Vacation Rentals By Owner In Key West, FL

$907.82

Waterfront Luxury Home with private pool!

Key West, Florida, United States

Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be in Coastal Comfort. This home is located in the private community of Key Cove Landings, on an exclusive lane of waterfront residential homes. The perks of this little-known location are many: walking distance to the essentials such a Publix grocery store and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. This home includes plenty of off-street parking in the private garages, as well as on the driveways in front of the house.brKey Feature:br3 en'suite bedroomsbrThis home’s highlight is the wall of floor-to-ceiling windows facing the water to provide the optimal view from every part of the house. The large open plan living room has a spacious seating area with plush couches around a large HD flat screen Smart TV. One of the couches also pulls out to a Queen-sized sleeper sofa for additional guests. There is a dining table with seating for up to 6 diners, with additional seating for 4 at the kitchen bar. brThe master bedroom has a King-sized bed, a large flat-screen HD TV, and an en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony. The second bedroom has a King-sized bed, a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The bathroom is en-suite. The third bedroom is also on the 2nd floor with a Queen bed, flat screen TV, balcony access and en-suite bathroom. On the main floor there is a fourth bedroom with trundle bed. There is a half bath down the hall.brOut back is one of the highlights of this home: the covered lanai and pool area. The covered outdoor dining area comfortably seats six for a poolside meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a pool lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for a poolside BBQ. brAMENITIES: Washer & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Heated Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).brbrDOG FRIENDLY. Please contact us to confirm specific pet policies.

4

Bed

3

Bath

8

Sleeps

$27718.28

/ Nightly

Hotel

Beachfront Key West + Free Breakfast, Pool & Spa

Key West, Florida, United States

Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resort. This adult-focused retreat blends historic island character with full access to one of Key West’s most iconic resort experiences. Guests enjoy stay at one, play at all access to the full Southernmost campus, including 3 heated pools, a private beach, oceanfront bars, tropical gardens, daily activities, and a world-class spa. Walk to the Southernmost Point, step onto South Beach, or spend the day exploring Old Town before returning to a peaceful guesthouse setting designed for laid-back island living.br✨ Why Guests Love Staying Herebrbr▶ Booking a room at The Guesthouses means enjoying an intimate boutique experience while gaining full stay at one, play at all access to the expansive Southernmost Beach Resort campus:brbr• Quiet End of Duval Street – Stay in the heart of the action but tucked away in a peaceful, sophisticated adult-focused sanctuary.brbr• Private Beach Access – Relax on the resort's exclusive tanning pier and private beach area with complimentary loungers.brbr• 3 Heated Pools – Choose your vibe between the lively Shores Pool, the tranquil Pineapple Pool, or the South Beach Pool.brbr• Tropical Gardens & Hammocks – Meander through award-winning lush grounds filled with hidden seating nooks and swaying hammocks.brbr• Daily Resort Activities – Enjoy poolside yoga, live music, and lawn games like cornhole and giant Jenga.brbr• Full-Service Concierge – Expert local advice for booking sunset sails, bike rentals, and the best island dining.brbrbr✨ Avalon King – Boutique Sophistication & Island Luxurybrbr▶ Located within the elegantly restored Avalon Guesthouse, the Avalon King is the epitome of Key West coastal chic. This room combines historic Victorian architecture with upscale, modern amenities, offering a serene haven for guests who want a refined, residential feel at the island's most famous address.brbr▶ Sleeping Arrangements:brbr• 1 King Bed with a plush pillow-top mattress and premium, high-thread-count linens.brbr• Sleeps up to 2 guests – A spacious, romantic sanctuary designed for couples seeking an elevated boutique experience.brbr▶ In-Room Features:brbr• Modern Beach-Chic Decor – Featuring bright, airy interiors, vaulted ceilings in select rooms, and sophisticated island finishes.brbr• Smart Mini-Refrigerator – Keep your champagne or tropical juices perfectly chilled.brbr• Gourmet Coffee Maker – Start your day with a high-end brew before stepping out onto Duval Street.brbr• Large Flat-Screen TV – Includes premium high-definition cable and easy-to-use streaming options.brbr• High-Speed Wi-Fi – Seamless high-speed connectivity throughout the Avalon and the wider resort.brbr• In-Room Safe, iron, and individual climate control for a tailored, comfortable environment.brbr▶ Bathroom:brbr• Contemporary Walk-in Shower with custom glass doors, designer tile, and high-end fixtures.brbr• Signature Bath Amenities, plush oversized towels, and a professional-grade hairdryer.brbrbr✨ A World of Food & Drinkbrbr▶ Between the Guesthouses and the main resort, you are steps away from fresh boat-to-table flavors and iconic Key West cocktails:brbr• Southernmost Beach Café – Oceanfront dining just 90 miles from Cuba. Enjoy a blend of Caribbean and classic Americana cuisine right on the sand.brbr• Shores Bar – Sip a signature Key Lime Colada while taking in stunning views of the Atlantic and South Beach.brbr• Pineapple Bar – A beautiful poolside retreat offering live music, house-made herb focaccia Beach Bread, and the famous Key Lime Margarita.brbr• The Parlour at Avalon Guesthouse – A quaint coffee and cocktail venue. Grab a drink and head to the porch for the best people-watching on Duval Street.brbr• The Coffee Shop – Located by the Café, serving fresh smoothies, juices, and pastries on a lovely oceanfront patio.brbrbr✨ Unmatched Resort Amenitiesbrbr▶ Your stay at The Guesthouses grants you the full luxury resort experience across the Southernmost campus:brbr• World-Class Spa – Indulge in ocean-side massages, facials, and signature body treatments.brbr• Fitness Center – Stay active with a state-of-the-art health club and weekly wellness classes.brbr• Tanning Pier – An iconic Key West landmark perfect for sunbathing or watching the Atlantic waves.brbr• Bicycle Rentals – Explore the island like a local with on-site rentals (additional fees apply).brbr• Lush Courtyards – Quiet, adult-friendly spaces perfect for reading or enjoying a glass of wine at sunset.brbrbr✨ Additional Detailsbrbr• Check-in: 4:00 PM | Check-out: 11:00 AM.brbr• Must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability.brbr• Adult-Focused: While the main resort is family-friendly, the Guesthouses (Avalon and Duval Gardens) are designed as adult-only retreats (18+).brbr• Minimum Age: Must be 21+ to check in at Southernmost Beach Resort.brbrIMPORTANT NOTE: Guests who do not check in as scheduled will be considered a no‑show.brbr• Pet Policy: At this time, pets are not permitted at The Guesthouses.brbr• Resort Fee: A mandatory fee of $73.13 per day is required (includes Wi-Fi, fitness center access, private beach chairs/umbrellas, bottled water, and daily resort activities).brbr• Security Deposit: A credit card pre-authorization of your total stay plus 15% for incidentals is required at check-in.brbr• Housekeeping: Professional daily service is included to ensure your historic retreat remains fresh and comfortable.brbr• Parking: Self-parking is available for $53.75 per night. One vehicle is allowed per guestroom reservation.brbr• Breakfast Included: Unlike the main resort rooms, bookings at The Guesthouses typically include a daily European-style breakfast spread.

1

Bed

1

Bath

2

Sleeps

$976.0

/ Nightly

Private Vacation Home

Mermaids Cove - Luxury Meets Location - 5BD/5.5Bath, May - August 10% off

Key West, Florida, United States

Welcome to Mermaid’s Cove, a stunning 5-bedroom, 5.5-bath luxury vacation home in the heart of Key West. Designed for comfort, connection, and a little bit of magic, this spacious retreat is perfect for large groups, families, girls’ trips, and multi-generational getaways.brbrWith all en-suite bedrooms, high-end finishes, and thoughtful design throughout, this home offers the perfect balance of privacy and togetherness.brbrSpacious Layout for Groups & Familiesbr • 5 Bedrooms | 5.5 Bathrooms | Sleeps 12+br • Every bedroom features a private en-suite bathbr • Two first-floor bedrooms ideal for guests who prefer no stairsbr • Third-floor loft with two queen beds – perfect for teens or a bonus hangout spacebrbrWhether you’re traveling with friends or family, everyone has room to relax in comfort.brbrOutdoor Oasis with Heated Pool & Hot TubbrbrStep into your own tropical sanctuary:br • Private heated pool (optional heating)br • Relaxing hot tub for evenings under the starsbr • Lush, secluded backyard perfect for entertainingbr • Ideal for morning coffee, poolside lounging, or sunset cocktails.brbrThis is the kind of backyard that makes you cancel plans… and stay in.brbrDesigned for Gathering & Entertainingbr • Large eat-in kitchen with gas stovebr • Open living spaces for connection and comfortbr • Perfect for group dinners, celebrations, or a private chef experiencebr • Charming upper and lower porches for quiet moments and island breezesbrbrbrUnbeatable Location – Walk to Duval Street and the Atlantic OceanbrbrLocation is everything, and Mermaid’s Cove delivers:br • 1 Mile from Duval Street (restaurants, nightlife, shopping)br • Close to Old Town Key West, beaches, and attractionsbr • Walkable, yet tucked away for peace and privacybrbrEnjoy the energy of Key West… then retreat to your own serene oasis.brbrWhy Guests Love Mermaid’s Covebr • Ideal for large groups & luxury travelersbr • En-suite bathrooms in every bedroom (rare find!)br • Prime Old Town / near Duval locationbr • Private pool + hot tub combobr • Perfect for birthdays, girls’ trips, family vacations, and special occasionsbrbrThe ExperiencebrbrThis isn’t just a rental.brIt’s where mornings start slow, afternoons turn golden, and nights stretch into laughter-filled memories.brbrbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. brPlease note due to city ordinance, this home has a minimum nightly stay of 28 nights.

5

Bed

5

Bath

12

Sleeps

$27631.45

/ Nightly

Hotel

Duval Street Stay + Free Breakfast, Beach & Pool

Key West, Florida, United States

Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resort. This adult-focused retreat blends historic island character with full access to one of Key West’s most iconic resort experiences. Guests enjoy stay at one, play at all access to the full Southernmost campus, including 3 heated pools, a private beach, oceanfront bars, tropical gardens, daily activities, and a world-class spa. Walk to the Southernmost Point, step onto South Beach, or spend the day exploring Old Town before returning to a peaceful guesthouse setting designed for laid-back island living.br✨ Why Guests Love Staying Herebrbr▶ Booking a room at The Guesthouses means enjoying an intimate boutique experience while gaining full stay at one, play at all access to the expansive Southernmost Beach Resort campus:brbr• Quiet End of Duval Street – Stay in the heart of the action but tucked away in a peaceful, sophisticated adult-focused sanctuary.brbr• Private Beach Access – Relax on the resort's exclusive tanning pier and private beach area with complimentary loungers.brbr• 3 Heated Pools – Choose your vibe between the lively Shores Pool, the tranquil Pineapple Pool, or the South Beach Pool.brbr• Tropical Gardens & Hammocks – Meander through award-winning lush grounds filled with hidden seating nooks and swaying hammocks.brbr• Daily Resort Activities – Enjoy poolside yoga, live music, and lawn games like cornhole and giant Jenga.brbr• Full-Service Concierge – Expert local advice for booking sunset sails, bike rentals, and the best island dining.brbrbr✨ Avalon Petite Queen – Sophisticated Island Efficiencybrbr▶ Located within the elegantly restored Avalon Guesthouse, the Petite Queen is a masterclass in stylish efficiency. This room offers a refined, beach-chic atmosphere within a historic Victorian setting, perfect for guests who want an upscale home base while spending their days exploring the island.brbr▶ Sleeping Arrangements:brbr• 1 Queen Bed with a premium pillow-top mattress and high-thread-count linens.brbr• Sleeps up to 2 guests – A cozy, intimate layout meticulously designed for the modern traveler.brbr▶ In-Room Features:brbr• Modern Coastal Decor – Featuring bright, airy finishes, local artwork, and sophisticated island-inspired touches.brbr• Smart Mini-Refrigerator – Keep your tropical drinks and snacks perfectly chilled.brbr• Gourmet Coffee Maker – Enjoy a high-quality morning brew before heading out to the resort pools.brbr• Flat-Screen TV – Equipped with high-definition cable and streaming capabilities.brbr• High-Speed Wi-Fi – Seamless connectivity included throughout the guesthouse and resort campus.brbr• In-Room Safe, iron, and individual climate control for a personalized, comfortable stay.brbr▶ Bathroom:brbr• Modern Walk-in Shower featuring designer tile work and excellent water pressure.brbr• Signature Bath Amenities, plush towels, and a professional-grade hairdryer.brbrbr✨ A World of Food & Drinkbrbr▶ Between the Guesthouses and the main resort, you are steps away from fresh boat-to-table flavors and iconic Key West cocktails:brbr• Southernmost Beach Café – Oceanfront dining just 90 miles from Cuba. Enjoy a blend of Caribbean and classic Americana cuisine right on the sand.brbr• Shores Bar – Sip a signature Key Lime Colada while taking in stunning views of the Atlantic and South Beach.brbr• Pineapple Bar – A beautiful poolside retreat offering live music, house-made herb focaccia Beach Bread, and the famous Key Lime Margarita.brbr• The Parlour at Avalon Guesthouse – A quaint coffee and cocktail venue. Grab a drink and head to the porch for the best people-watching on Duval Street.brbr• The Coffee Shop – Located by the Café, serving fresh smoothies, juices, and pastries on a lovely oceanfront patio.brbrbr✨ Unmatched Resort Amenitiesbrbr▶ Your stay at The Guesthouses grants you the full luxury resort experience across the Southernmost campus:brbr• World-Class Spa – Indulge in ocean-side massages, facials, and signature body treatments.brbr• Fitness Center – Stay active with a state-of-the-art health club and weekly wellness classes.brbr• Tanning Pier – An iconic Key West landmark perfect for sunbathing or watching the Atlantic waves.brbr• Bicycle Rentals – Explore the island like a local with on-site rentals (additional fees apply).brbr• Lush Courtyards – Quiet, adult-friendly spaces perfect for reading or enjoying a glass of wine at sunset.brbrbr✨ Additional Detailsbrbr• Check-in: 4:00 PM | Check-out: 11:00 AM.brbr• Must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability.brbr• Adult-Focused: While the main resort is family-friendly, the Guesthouses (Avalon and Duval Gardens) are designed as adult-only retreats (18+).brbr• Minimum Age: Must be 21+ to check in at Southernmost Beach Resort.brbrIMPORTANT NOTE: Guests who do not check in as scheduled will be considered a no‑show.brbr• Pet Policy: At this time, pets are not permitted at The Guesthouses.brbr• Resort Fee: A mandatory fee of $73.13 per day is required (includes Wi-Fi, fitness center access, private beach chairs/umbrellas, bottled water, and daily resort activities).brbr• Security Deposit: A credit card pre-authorization of your total stay plus 15% for incidentals is required at check-in.brbr• Housekeeping: Professional daily service is included to ensure your historic retreat remains fresh and comfortable.brbr• Parking: Self-parking is available for $53.75 per night. One vehicle is allowed per guestroom reservation.brbr• Breakfast Included: Unlike the main resort rooms, bookings at The Guesthouses typically include a daily European-style breakfast spread.

1

Bed

1

Bath

2

Sleeps

$320.6

/ Nightly

House Boat

53' Vintage 3-bedroom Houseboat with AC & Pontoon`

Key West, Florida, United States

Discover the charm of “Old Key West” aboard Vita Felice and embark on the journey of a lifetime by staying on a Luxurious Vintage Yacht and a piece of American History. This stay is paired with a Self Drive 20' Sun Tracker Pontoon Boat for Fishing/Lobstering, Cruising and Exploring the Sandbars. Enjoy local resturants with provided docks for the pontoon to enjoy night life. The location near downtown Key West is perfect for exploring the island on land but also provides a great opportunity to enjoy activities normally provided by boat charters. This unique opportunity gives you a secluded stay with a beautiful open water view unmatched by any other Key West lodging but also gives you freedom of water activities that would normally require a charter. Fishing, lobstering, and snorkeling are among many of the activities, including exploring on the Pontoon boat that can be used for island hopping and sandbars.brbrThis Yacht was “The first Hatteras” certified for charter and is anchored offshore Key West Island and it’s accessible with the paired Pontoon Boat. This elegant vessel offers a timeless escape into the Grandeur of the Past in True Old Key West Style. Experience authentic boating living in the ocean at anchor with a secluded tropical paradise on the water, WITHOUT neighbors in close proximity! Anchored just a short pontoon boat ride from land. brbrThe Pontoon rental for this boat is required and is the deposit for your nightly stay. Deposit is paid within 3 Days after you book your nightly stay. Pricing for the Pontoon is $250 per day depending on the length of your stay and is a bareboat rental that can be self drive or you can hire a captain to drive you and a list of captains can be provided.brbrExperience the Enchantment of Key West and unwind while Lobstering/Snorkeling, Swimming or Fishing, and Capture a Breathtaking Iconic Sunset at Sea!brbr#Provided Equipment (No extra charge):brSnorkeling GearbrLobstering Kits brbrThis yacht offers everything you could desire! Perfect for Catch, Clean & Cook videos to share with friends and family.brbr#2017 Sun Tracker DXL Fishin Barge Pontoon Boat brBareboat Rental (For Entire Stay)– Self Dive or Hire CaptainbrSpacious Deck with Comfortable Cushion 10 person seating and small tablebrIdeal for Fishing (fishing pole holders)brWater ladder for Snorkeling/LobsteringbrGarmin GPS for navigationbrBluetooth Sound for Smartphone brBimini Top for shadebrbr#1972 53' Hatteras MotoryachtbrAmenities On Deck! brSpacious Bow & Aft DeckbrBow Cushions for Lounging and SunbathingbrAft Deck Chairs & Couch for Entertaining brOutdoor Sink & Tables for Cooking & Cleaning your Catch , Inside full kitchen for cooking.brColor-changing led lightsbr brInside, Features Beautifully Preserved Original Mahogany Woodwork and Down Helm for Authentic Boating Experience and Pictures to Document and Share of Your Vacation.brbr#The Main Salon Includes:brBose sound bar system brSmart TV brWi-FibrColor-changing led lightsbrElectric CoolerbrDedicated A/C brTwo Convertible Couches Option into Two Twin Beds or a California King Bedbrbr#This Yacht comes Equipped with a Full Kitchen with Modern Home-Sized Appliances: brFull Sized Refrigerator brFull Sized 4 Burner Flat Range with OvenbrLarge Microwave brComplete Cookware and DishesbrToaster brTea KettlebrPantrybrbr#The Captain's Quarters Accommodations: brQueen Walk-Around Bed Nautical-Themed Bedding with Memory Foam ToppersbrTwo End Tables with Lampsbr32” Smart TVbrDedicated A/CbrAmple LightingbrFull ClosetbrEn Suite Full Private Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The Guest Cabin: brTwo Single Beds with Nautical-Themed Bedding with Memory Foam ToppersbrFull ClosetbrDedicated A/CbrFull Guest Bathroom Stocked with Fluffy Towels, Hair Dryers and Complimentary Toiletriesbrbr#The V Berth includes: brBunk Beds with Nautical-Themed Bedding with Memory Foam ToppersbrDedicated A/CbrWasher/Dryer Combobr Linen Closet brExtended Shower Room with Vanity Stocked with Fluffy Towels, Hair Dryers and Complimentary ToiletriesbrbrVita Felice is Perfect for your next Special Occasion or Fun Getaway! brComplete with its Extensive Accommodations and Amenities! brbr#Spacious Timeless Classic Yacht for Events:brCelebration of Life/Memorial CeremonybrBachelor/Bachelorette PartiesbrProposalsbrHoneymoonbrBirthday Party'sbrOthersbrbrBE SAFE !brbr

Bed

Bath

Sleeps

$695.54

/ Nightly

Condo

**TOP OF OLD TOWN @ DUVAL SQUARE** Renovated Home + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrPerched above the sights and sounds of Duval Street, sits TOP OF OLD TOWN, a recently renovated 2-bedroom private home, located within a secluded community in the heart of Old Town. This hidden gem offers a spacious interior, multiple outdoor spaces, and access to the community pool. Combined with Last Key Realty’s Five Star Guest Services & Complimentary Concierge, your stay at TOP OF OLD TOWN will leave you feeling on top of the world.brbrTHE LOCATION & COMMUNITY...brbrTOP OF OLD TOWN is located in the Duval Square community, with entrances from Duval, Virginia, and Simonton Streets. This location means you'll enjoy the convenience of having shops, restaurants, and art galleries right at your doorstep. Take a refreshing dip in the beautiful community pool or unwind in the spacious common area overlooking the bustling street below.brbrNo visit to Key West would be complete without a selfie at the iconic Southernmost Point Buoy, which is located just a few blocks away. You’ll also be within walking distance to several of Key West's best and most unique restaurants, including Martin’s, Moondog Cafe and 915. While you won't need a car to get around, this condo does include one covered, off-street parking space in the parking garage.brbrTHE LIVING AREA...brbrStep inside and be greeted by a bright and airy, open concept living space. Relax on the plush sofa, which converts to a queen sleeper for extra guests, and enjoy your favorite shows on the large flat-screen TV. The adjacent dining area comfortably seats six, perfect for gathering with friends and family.brbrThe fully equipped kitchen is a chef's dream, featuring new luxury appliances and all the essentials you need to whip up delicious meals. Prefer to dine al fresco Step out onto your private covered balcony and savor your meal while soaking up the lively atmosphere of Duval Street.brbrTHE ACCOMMODATIONS...brbr** Master Bedroom - Located on the Second Floor with a King bed, flat-screen TV, full closet, balcony access and an en-suite bathroom with a walk-in shower.brbr** Guest Bedroom - Located on the Second Floor with a King bed, flat-screen TV, full closet, and an en-suite bathroom with a walk-in shower.brbr** The Living Area sofa pulls out to a Queen-size bed.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TV in Living Roombr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & Cable TV includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked condo also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Assigned off-street carport for 1 carbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Not Allowedbr** No Smoking Allowed - not even on the porchbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

Bed

Bath

Sleeps

$221.52

/ Nightly

Condo

J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point & Shared Pool!

Key West, Florida, United States

Welcome to J Ferrara, your ideal retreat in the heart of Key West! brbr brbrNestled on a quiet street in the artist-inspired condominium complex in Bahama Village, The Galleria has a rich history dating back to the early 1900s. It was once a popular spot for traveling artists who came to Key West for inspiration and showcased their work in the nearby art galleries on Duval Street. Our cozy studio offers a peaceful base for your fun, adventurous vacation. Just 10 blocks from the beach & a short 2.5 blocks from the famous Duval Street, our location provides easy access to the best of Key West. Whether you're returning from a day of sun & sand, a boat excursion, or a leisurely stroll down Duval Street, our studio is the perfect Old Town Key West stay! Our vacation rental is named after one of our dear and talented friends, James Ferrara of J Ferrara Gallery. Based in South Florida, James specializes in underwater photography. You will find several of his pieces throughout the room! Whether you seek relaxation, adventure, or a mix of both, J Ferrara provides the perfect base for your Key West getaway. brbr brbrSLEEPS MAXIMUM OF 2 GUESTS: brbr brbrBedroom: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrKitchenette: Lightly Equipped (dorm size refrigerator/freezer, sink, microwave, Keurig, drip coffee maker) brbr brbrAMENITIES: brbr brbr- Shared Heated (Nov-Apr) Pool brbr brbr- Shared Laundry brbr brbr- Shared Bike Rack brbr brbr- Shared Propane BBQ Grill & Picnic Area brbr brbr- Keurig & Drip Coffee Maker brbr brbr- Linen's and Bath/Pool Towels Provided brbr brbr- Street Parking available, no off-street/designated parking available brbr brbr- 2.5 blocks to Duval Street brbr brbr- 0.4 miles to Southernmost Point brbr brbr- 0.7 miles to Fort Zachary Taylor State Park/Beach brbr brbr- 1.1 miles to Mallory Square Sunset Pier brbr brbr- 1.2 miles to Key West Historic Seaport brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrUnit Size: Please be aware, this unit is a cozy 138 sq. ft. studio—while compact, it provides all the essentials for a comfortable and enjoyable stay. brbr brbrAge and Occupancy Requirements: Booking tenant must be 25 years of age or older and must occupy the property for the entire duration of the booking. Furthermore, this property is exclusively available as a vacation rental and is not available for worker housing. brbr brbrNo Smoking: Smoking is strictly prohibited within the property to maintain a smoke-free environment for all guests. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time. brbr brbrSecurity Cameras: For the safety and security of guests and property, exterior security cameras monitor all exterior areas of the complex. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

1

Bath

2

Sleeps

Exceptional(20)

$2368.25

/ Nightly

Private Vacation Home

BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST

Key West, Florida, United States

A Castle on an Island On A Privately Owned Key West IslandbrbrPrivate Bridge for Cars and Trucks connected to Key WestbrbrFrom the Era of the Great Gatsby, in 1926, one of the richest men in South Florida, his family owned 45 percent of the land in Key West and most all of the shrimp and fishing boats in the Keys, married a beautiful young New York socialite and wanted her to move to Key West to live with him. Honey, I will only move to Key West if you build me a Castle on an Island. So it was!!brbrFor almost a century, this special Island has hosted a presidents, governors and business leaders for meetings, celebrations and parties. This historical property has been restored to its original beautiful stately manner , furnished in modern hip hop Gatsby Style from the recent movie, and now is available for you to host your colleagues, families, and friends for business meetings, educational conferences, and special family events,.brbrThis is one of the most historic, beautiful and expensive properties in Key West, A 35 million dollars private Island, connected to Key West by a bridge and only 8 short minutes to Duval Street. This is a controlled access, gated island community.brbrYour friends, family and colleagues can make your private island, their meeting place for time in the Key West and the Florida Keys. On your own secluded and secure gated Island,, only 10 minutes to the downtown area, you can enjoy the refreshing trade winds while you meet with your group. The properties boasts some 25 rooms to host your activities, whether formal meetings or just a simple game of teambuilding Volleyball and then a swim in either the salt water pool or fresh water pool, you will enjoy the best the Florida Keys has to offer.brbrOTHER AMENITIESbrbrFULL AIR CONDITIONINGbrbrPRIVATE SMALL BEACH AREAbrbr5 ACRE SECURE GATED ISLANDbrbr4 KAYAKS,brbr2 PADDLEBOARDSbrbrJACUZZIbrbrPOOLVOLLEYBALL COURT (Sand)brbrDOCK AND BOAT SLIPS WITH FISHING and FISH CLEANING AREAbrbrTENNIS COURT (OFF SITE)brbrBASKETBALL HOOPbrbrPOOL TABLEbrbr10 FLAT SCREENSbrbrMULTIPLE WIFI (INCLUDING 5G) NETWORKSbrbrRACKETBALL COURT (OFFSITE /OPTIONAL)brbr2 LARGE OCEANVIEW PORCHESbrbrBedroom and Sleep InfobrbrThe VERY LARGE MASTER is 600 sq. feet with a private bathroom, shower and tub, and has 2 king beds.brbrThe Coral Room, about the size of an average master has a king bed with private bath, shower and tubbrbrThe Ocean Room has a king bed and private bathroom with tub and shower.brbrThe Turtle Room has a king bed with private bathroom with showerbrbrThe Gatsby Room has a king bed with bathroom and shared shower.brbrINCLUDED NO EXTRA CHARGE The Mango Tree Cottage had a large living room, a full kitchen, 2 larger bedrooms with kings, and 2 private bathrooms with showers.brbrbrbrOPTIONAL EXTRA FEEbrbrThe Mermaid's Cottage is very modern with a small living area and small full kitchen, very large bedroom with a king bed and a bathroom with shower.brbrOPTIONAL EXTRA FEE BEACH COTTAGEbrbrThe Beach Cottage is very modern with a small living area, very large bedroom with a king bed and a bathroom with shower.brbrPLEASE CALL FOR MORE INFObrThanks Andrew cell 305 923 6480

9

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8

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20

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$337.5

/ Nightly

Condo

Downtown Sunset Harbor Studio!

Key West, Florida, United States

This is a great studio unit at Hyatt Sunset Harbor in downtown Key West. Walk along the boardwalk or head to Duval Street only a couple blocks away. The resort has pool, hot tub, and grills for use during your stay.brbrThere are laundry facilities on site free of charge. There are NO daily resort fees, but parking is extra.brbrEach unit has a King sized bed, kitchenette with microwave and mini fridge, and bathroom.brbrWeeks are Sun-Sun.

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Private Vacation Home

Southernmost View - Private Pool

Key West, Florida, United States

Summary:brbrSouthernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps from the beach as well as the Southernmost Point of the continental USA. Turquoise blue waters await you on the rooftop sundeck - perfect for tanning, reading and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.brbrbrbrThe Space:brbrEnjoy this perfect upscale beach vacation home in its convenient location. You can walk or bike along the pathways to all of your favorite attractions.brbrbrbrThis home features a fully-equipped gourmet kitchen adorned with white marble countertops and spacious cooktops. Cook today’s catch on the Weber grill and unwind over dinner at the kitchen table for six. The small pool is surrounded by natural wood decking.brbrbrbrWith four bedrooms, three and a half baths, a private washer/dryer and parking, what more could your next Key West getaway need This home is a rare find on the island making it a perfect spot for groups and accommodating your extended family. brbrbrbrTwo master suites include king size beds and en suite baths. While the Jack and Jill bathroom splits two additional bedrooms, one with a king size bed the other with two twin beds. This home sleeps up to eight guests and it can be rented for a 28-night minimum in the best tropical location.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guest will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrFind yourself on world famous Duval Street, just one short block away, for shopping, dining, and year-round entertainment and special events. Visit the Key West Butterfly and Nature Conservatory (also on Duval Street) to see over 50 butterfly species along with a number of exotic birds from around the world. Head over to Fort Zachary Taylor Historic State Park to explore the fort and hit the sandy beaches, just a little over a mile away, and don't forget to take a selfie by the Southernmost Point Buoy located just a few steps from your rental at the end of Whitehead.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close in proximity you are to everything. Don’t feel like walking Peddle your way to breakfast, or take a bike ride along the water at sunset. Rent your bikes from Fury or Island Bicycles who offer both pick up & drop off services to your home! Feel like you’re on island time when you rent from Minty’s where you can enjoy exploring Key West on a scooter or golf cart. In addition to these non-traditional modes of transportation, you can also Uber, Lyft or Taxi to your next destination. Pink Taxi is an easy, reliable and affordable way for getting to your rental from the airport.brbrbrbrThis stand alone home also includes a private assigned parking space in the gated community.brbrbrbrOther Things to Note:brbrThis unit is pet friendly! brbrAssigned parking included for 1 vehiclebrbrPrivate gated communitybrbrHouse features private grillbrbrPool is heatedbrbrBuilt to current hurricane-resistant codes with 180 mph windows and doorsbrbrMid-stay cleans are available upon request.brbr28-night minimum

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$283.73

/ Nightly

Guest House

NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Key West, Florida, United States

PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...brSteeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Night Watch room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his secret cellar - one of the few basements in Key West! You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.br***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.brbrDETAILS AND AMENITIES...brOn the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.brbrSLEEPING ARRANGEMENTS...brThe Night Watch room is located downstairs and offers a king bed, a stocked kitchenette, a shower bathroom and a hanging closet for your convenience.brbrOUTDOOR LIVING...brTake in the island air and sip on your frosted cocktail just outside of your room, with semi-private seating. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. brbrPARKING...brParking is limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.brbrPETS...brThis is not a pet-friendly inn.brbrCancellations requested at least 30 days prior to arrival receive a full refund.brCancellations requested at least 14 days prior to arrival receive a 50% refund.brbrJOIN THE ADVENTURE...

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$529.81

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Condo

Truman Annex Best Location in Town

Key West, Florida, United States

We stick to a Saturday check in during the in season months (Jan-April)brbrGreetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita.brbr'Margarita Villas' are located in historic Old Town in a beautiful, very private gated compound that has won awards as the best development in Florida. (And yes it does have a blender).brbrIt’s just off Duval Street, with its bustling shops and nightlife; yet quiet and private. Fort Zachary Taylor on the south side of the property has one of our most picturesque beaches located among the tall whispering pines of the uplands; the view of the reef and the turquoise waters is magnificent.brbrThe heated pool is conveniently located nearby so you are never far from a refreshing dip or just 'conching out' in the sun.brbrThere are two bedrooms and one baths; the master bedroom is furnished with a queen-size bed, the other, two twins. French doors in the living room open onto the garden deck for outdoor dining or to catch the tropical breezes. Outdoor porch furniture on the deck.brbrThe kitchen is completely equipped (including the mandatory BLENDER).brbrFully air-conditioned, all rooms have tropical ceiling fans and all linens are provided. There is off street parking for one car.brbr brMike WernicoffbrbrPS: Did I mention that we have a BLENDER brbrKeywords: Condominiumbr

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$916.2

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Private Vacation Home

Villa Porta del Sole - 3BR Sunset Key Villa with Private Pool, Direct Beach Access and Sunset Ocean View!

Key West, Florida, United States

Staying on Sunset Key is always magical—but even more so when you’re in one of the few homes with a completely unobstructed view of the western horizon. For unmatched sunset watching from your private sandy beach or king suite balcony, tropical birds visiting your tranquil backyard, and slow mornings by the pool, welcome to Villa Porta del Sole.brbrThis standout property at 10 Sunset Key is the beloved island home of a world champion sailor, whose maximal nautical style immerses you in ocean life without ever leaving land. Vaulted ceilings, model helms and monohulls, coiled ropes, and other seafaring details fill the living room, which sits just off a calming blue kitchen and overlooks the pool and ocean beyond. The main level also features a spacious king bedroom with a full bathroom and direct walkout to the covered porch.brbrUpstairs, you’ll find two additional bedrooms. One is a master suite with a king bed, full bath, and private balcony—complete with a hammock for siestas or quiet downtime. The second is a lofted bedroom overlooking the living area, furnished with two twin beds that can be converted into a king. This room also includes a full bathroom.brbrThe outdoor space is where 10 Sunset Key truly shines. A large, covered porch offers both shaded and sunny seating areas, plus a grill and prep station. The heated pool invites gathering, play, and relaxation. Just beyond, a private footpath leads to your own sandy beach with plenty of seating—perfect for watching ships drift past the horizon, spotting birds in flight, and cherishing the joy on your family’s faces.brbrRestrictions: Smoke free house. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.

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$2193.75

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Hotel Resort

Celebrate New Years Eve in Key West @ Exclusive Hyatt Windward - SLEEPS 6 !

Key West, Florida, United States

IMPORTANT...THIS RENTAL IS AVAILABLE FOR ONE NIGHT CHECKING IN DECEMBER 31, 2024 AND CHECKING OUT JANUARY 1ST, 2025. PLEASE WHEN RESERVING MAKE SURE YOU SELECT THESE CHECK-IN AND CHECK-OUT DATES OR THE RESERVATION CANNOT BE ACCEPTED....THANK YOUbrbrTwo Bedroom Villa with Ocean ViewbrSleeps 6brbrWhether you choose to spend your days simply relaxing by the infinity pool or setting off on a dive adventure, Key West delivers a dream vacation of your own design. Your island home is just minutes away from celebrating the sunset each evening at Mallory Square and taking in the renowned dining, shopping and nightlife of Duval Street.brbrHyatt Windward Pointe offers and ideal respite from reality. Located on the southeast end of Key West, this seaside resort will immediately capture your soul and transport you to the casual comfort of the islands.brbrHotel Features br•Wi Fi Blu-Ray Home Theatre Systembr•Accommodates 6 peoplebr•Comfortably Appointed Two Bedroom/Bathroom Units with King-Sized Beds in Master Suitebr•Fully Equipped Kitchens with Separate Dining Roomsbr•Shuttle to/from Key West International Airport & to/from Old Town Feebr•Complimentary Wireless High-Speed Internet Accessbr•Maps & Directionsbr•Complimentary Parkingbr•Fully equipped kitchensbr•Pool side Abbey Road Snack Shackbr•Fine local diningbr•Pool & Spabr•Bicycle rentals and barbeque grillsbr•Volleyball courtbr•Shuffleboardbr•Ping Pong/Pool TablebrbrGuest Services brWelcome to Hyatt Windward Pointe, A Hyatt Residence Club. We believe great destinations in Key West should offer more than a good night's sleep, and we take pride in offering you the best of everything -- a great location, luxurious rooms and unparalleled service. Whether your stay in Key West is for business or pleasure, it should be a worry-free experience that delights your senses. So choose Hyatt Windward Pointe, A Hyatt Residence Club. We assure you the best stay in Key West. brbrTwo Bedroom / Two Bath Residence Includes:brAtlantic ocean, pool or lush courtyard views and lavish plantation-style decor welcome you to a two-bedroom condominium offering a master suite with king bed and adjoining bath with walk-in shower and jetted tub, and guest bedroom with queen bed and full bath. Deluxe amenities include full kitchen, dining area, living room with TV and stereo CD player, furnished balcony and wireless Internet.brbrAmenities: br •Additional TV(s) in bedroom(s)br•Wi-Fi Blu-ray Home Theater Systembr•37 Flat Screen TV in Living Room and Master Bedroombr•26 Flat Screen TV in Guest Bedroombr•Hairdryerbr•Iron/ironing boardbr•Washer/dryerbr•Dining areabr•Refrigeratorbr•Microwavebr•Coffee makerbr•Dishwasherbr•Conventional oven with stove topbr•Additional TV(s) in bedroom(s)br•Cable/satellite TV channelsbr•Stereo systembr•Three telephonesbr•Voicemailbr•High-speed Internet accessbr•Dataportbr•Complimentary Wi-Fi and High Speed Internet Accessbr•Concierge during regular hoursbr•In-room safebr•Maximum guests per room: 6br•Walk-in showerbr•Spa tubbr•Separate sitting areabr•Fully equipped kitchenbr•Balconybr•Individual Climate Controlbr•iHomebrbr$60.00 Fee due upon check out at concierge

2

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2

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6

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$975.31

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Private Vacation Home

Oceanview home with private pool & lush landscaping!

Key West, Florida, United States

Banana Breeze is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasis in a private waterfront retreat, with your own heated pool. brLook out at the open water views while enjoying the professionally decorated interior and spacious outdoor patio. Imagine relaxing at Banana Breeze with friends, family or both while listening to island music and casting away into delightful bliss. brbrKey Cove estates is an exclusive group of homes all located on the waterfront and provides hard to find privacy. Centrally located in the middle of Key West, you and your guests will have the convenience of walking to grocery stores as well as shopping just across the street. Old Town, Key West's Historic area is just a few minutes away by transportation. Whether you bring your own vehicle or rent one of the many local options like mopeds, electric cars, or bikes, you can easily park in one of two garages or your own private driveway. brbrThe first floor of the home is located atop of a grand set of exterior stairs which lead you to the front door, through which you will find a expansive floorplan consisting of a professional kitchen fully functional for even the most advanced chefs. This area also consists of a large living room and dining area suitable for all your guests to congregate. The far wall is comprised of glass doors allowing breathtaking views at the Florida Bay and the waters edge below. This floor as a whole is your central area for entertaining guests and gathering families together. brbrAccommodationsbrThis home has one master suite located on the top floor. The master bedroom has a King sized bed and a beautiful en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate facilities room. The bedroom opens out to your waterfront balcony, with gorgeous water view. brThe other rooms are down the hallway, one with a Queen size bed and the other third bedroom has two twin beds that may be converted into 1 King upon request, with ample notice. Both have a glass sliding door with access to the same waterfront balcony and share a full bathroom. On the main floor there is a fourth bedroom with two twin beds that also seamlessly convert to a King bed, upon request and a full bathroom down the hall for convenience.brbrOutdoor EntertainingbrOn the ground floor is one of the highlights of this home: the outdoor landing and entertainment area with a heated kidney shaped pool. The outdoor dining area comfortably seats six for an outdoor meal. The pool is heavenly, with views of the open water and visiting heron on the tropical greenery that surrounds the back yard. There is also a lounge area with comfortable chaises in a piece of deck that gets equal sunshine and shade. The backyard is complete with a large propane grill for BBQs. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc.brEach floor has its own outdoor area with furnishings for what ever your mood might be. Whether you'd like to entertain a larger group on the ground floor, or have a more intimate occasion on the first floor balcony overlooking the water, or if you'd simply like to take in the morning views while sipping coffee out your master suite, Banana Breeze offers numerous different options brbrAMENITIES...brWasher & Dryer, Central Heat and A/C, Ceiling Fans, Off-Street Parking in Garage & on Driveway, Flat Screen State-of-the Art Smart HD TVs in all bedrooms and main living area, Fully Equipped Chef’s Kitchen with Gourmet Appliances, Private Pool, Large BBQ Grill, Linens and Towels provided. Interim housekeeping provided upon request. Wireless high-speed Internet access and full cable is included. Pets Considered. This property will accommodate 8 guests.brbrDockage is not available at this home's development.brbrRATES: we have 3 night (not always available) and 4 night rates available. We also have a 7 night and 21+ night discounted rate (automatically provided with dates).

4

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3

Bath

8

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$299.03

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Condo

Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews

Key West, Florida, United States

If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bedroom condo you are greeted with a beautiful view the Atlantic Ocean. Completely upgraded with all new furniture and large flat screen televisions. The kitchen is upgraded and room for two chefs. The master bedroom has a king bed and en suite bathroom with large flat screen television. Top of the line queen sleeper for your guests and an indoor dinning room table set for those special meals. Relax from your private balcony that overlooks the ocean and one of Key West largest beaches or enjoy the large resort-style community pool with Jacuzzi. There is a bbq grill area for your use as well as a tennis court. Free wi-fi and free covered parking bay. brDon't miss this one...book today!brbrNote: The property is set up for no contact check-in. The unit has been cleaned and sanitized by a professional cleaning company prior to your arrival. If Key West closes to tourists due to COVID related travel shutdown, you will recieve 100% refund minus credit card fee of 3.5%.

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1

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2

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$26537.95

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Hotel

Key West Beach Stay + Free Breakfast, Pool & Spa

Key West, Florida, United States

Escape to the quiet end of Duval Street and enjoy a refined Key West stay at The Guesthouses at Southernmost Beach Resort. This adult-focused retreat blends historic island character with full access to one of Key West’s most iconic resort experiences. Guests enjoy stay at one, play at all access to the full Southernmost campus, including 3 heated pools, a private beach, oceanfront bars, tropical gardens, daily activities, and a world-class spa. Walk to the Southernmost Point, step onto South Beach, or spend the day exploring Old Town before returning to a peaceful guesthouse setting designed for laid-back island living.br✨ Why Guests Love Staying Herebrbr▶ Booking a room at The Guesthouses means enjoying an intimate boutique experience while gaining full stay at one, play at all access to the expansive Southernmost Beach Resort campus:brbr• Quiet End of Duval Street – Stay in the heart of the action but tucked away in a peaceful, sophisticated adult-focused sanctuary.brbr• Private Beach Access – Relax on the resort's exclusive tanning pier and private beach area with complimentary loungers.brbr• 3 Heated Pools – Choose your vibe between the lively Shores Pool, the tranquil Pineapple Pool, or the South Beach Pool.brbr• Tropical Gardens & Hammocks – Meander through award-winning lush grounds filled with hidden seating nooks and swaying hammocks.brbr• Daily Resort Activities – Enjoy poolside yoga, live music, and lawn games like cornhole and giant Jenga.brbr• Full-Service Concierge – Expert local advice for booking sunset sails, bike rentals, and the best island dining.brbrbr✨ Duval Gardens Petite Queen – Cozy Historic Charmbrbr▶ Located within the beautifully restored Duval Gardens house, the Petite Queen is a masterclass in beach-chic efficiency. This room offers a cozy, historic Key West vibe, perfect for solo travelers or couples who prioritize a prime location and stylish comfort.brbr▶ Sleeping Arrangements:brbr• 1 Queen Bed with a premium pillow-top mattress and high-thread-count linens.brbr• Sleeps up to 2 guests – A compact and intimate layout designed for the modern island explorer.brbr▶ In-Room Features:brbr• Island-Inspired Decor – Features local artwork, soft coastal tones, and bright, airy finishes.brbr• Smart Mini-Refrigerator – Keep your tropical refreshments chilled and ready.brbr• Gourmet Coffee Maker – Start your morning with a fresh brew before heading to the beach.brbr• Flat-Screen TV – Includes high-definition cable and easy-to-use streaming interfaces.brbr• High-Speed Wi-Fi – Seamless connectivity included in your resort stay.brbr• In-Room Safe, iron, and individual climate control for total comfort.brbr▶ Bathroom:brbr• Modern Walk-in Shower with custom tile work and refreshing water pressure.brbr• Signature Bath Amenities, plush towels, and a professional-grade hairdryer.brbrbr✨ A World of Food & Drinkbrbr▶ Between the Guesthouses and the main resort, you are steps away from fresh boat-to-table flavors and iconic Key West cocktails:brbr• Southernmost Beach Café – Oceanfront dining just 90 miles from Cuba. Enjoy a blend of Caribbean and classic Americana cuisine right on the sand.brbr• Shores Bar – Sip a signature Key Lime Colada while taking in stunning views of the Atlantic and South Beach.brbr• Pineapple Bar – A beautiful poolside retreat offering live music, house-made herb focaccia Beach Bread, and the famous Key Lime Margarita.brbr• The Parlour at Avalon Guesthouse – A quaint coffee and cocktail venue. Grab a drink and head to the porch for the best people-watching on Duval Street.brbr• The Coffee Shop – Located by the Café, serving fresh smoothies, juices, and pastries on a lovely oceanfront patio.brbrbr✨ Unmatched Resort Amenitiesbrbr▶ Your stay at The Guesthouses grants you the full luxury resort experience across the Southernmost campus:brbr• World-Class Spa – Indulge in ocean-side massages, facials, and signature body treatments.brbr• Fitness Center – Stay active with a state-of-the-art health club and weekly wellness classes.brbr• Tanning Pier – An iconic Key West landmark perfect for sunbathing or watching the Atlantic waves.brbr• Bicycle Rentals – Explore the island like a local with on-site rentals (additional fees apply).brbr• Lush Courtyards – Quiet, adult-friendly spaces perfect for reading or enjoying a glass of wine at sunset.brbrbr✨ Additional Detailsbrbr• Check-in: 4:00 PM | Check-out: 11:00 AM.brbr• Must show a valid photo ID and credit card upon check-in. Please note that all special requests cannot be guaranteed and are subject to availability.brbr• Adult-Focused: While the main resort is family-friendly, the Guesthouses (Avalon and Duval Gardens) are designed as adult-only retreats (18+).brbr• Minimum Age: Must be 21+ to check in at Southernmost Beach Resort.brbrIMPORTANT NOTE: Guests who do not check in as scheduled will be considered a no‑show.brbr• Pet Policy: At this time, pets are not permitted at The Guesthouses.brbr• Resort Fee: A mandatory fee of $73.13 per day is required (includes Wi-Fi, fitness center access, private beach chairs/umbrellas, bottled water, and daily resort activities).brbr• Security Deposit: A credit card pre-authorization of your total stay plus 15% for incidentals is required at check-in.brbr• Housekeeping: Professional daily service is included to ensure your historic retreat remains fresh and comfortable.brbr• Parking: Self-parking is available for $53.75 per night. One vehicle is allowed per guestroom reservation.brbr• Breakfast Included: Unlike the main resort rooms, bookings at The Guesthouses typically include a daily European-style breakfast spread.

1

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1

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2

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$308.2

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Condo

The Cat Island Suite | Charmingly Renovated w/ Pool

Key West, Florida, United States

The Cat Island Suite | Updated! Stunning Sunset View, Pool!brbrEscape to The Cat Island Suite, a serene, beautifully updated, and well-appointed 2-bedroom condo located in the peaceful Sunrise Suites community on the east side of Key West. Just a mile from the beach, this charming getaway provides the perfect combination of relaxation and adventure. Whether you're lounging by the pool, exploring nearby attractions, or enjoying the comfort of your condo, The Cat Island Suite is the ideal place to unwind and create lasting memories.brbrThe Ambiance:brStep into The Cat Island Suite and experience a delightful blend of modern tropical charm. This stylish condo features luxurious finishes and an open-concept kitchen and living room layout that's perfect for gathering with family or friends. The two-bedroom suite accommodates up to four guests, offering:brbr- King-sized bed in the primary bedroombr- Queen-sized bed in the second bedroombrbrThe primary bedroom features a beautiful ensuite bathroom complete with modern walk-in shower, perfect for that spa-like feel. The fully equipped kitchen makes preparing meals a breeze, whether you're brewing your morning coffee with the Keurig or cooking on the electric stove. Relax on your private balcony and take in the views, or enjoy TV, WiFi, and central air conditioning for added comfort.brbrGuest Access:brEnjoy a seamless arrival with our contactless check-in process, where you'll receive a personalized access code to enter your unit. During your stay, make the most of the shared amenities, including:brbr- Shared heated pool and hot tubbr- Tennis courtbr- Walking paths and biking trailsbrbrLocation Highlights:brThe Cat Island Suite is ideally located within the peaceful Sunrise Suites Resort, just a short distance from Key West's best attractions. A quick 10-minute drive takes you to the lively Duval Street, where you'll find a vibrant selection of restaurants, bars, and entertainment. The Key West Airport is also just a short drive away, making travel easy and stress-free.brbrGetting Around: brWith parking available, you'll have convenient access to explore the island by car. For those who prefer to travel by bike, scooter, or golf cart, rentals are available nearby. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- The pool and hot tub are shared with other guests of the complex.br- No pets allowed in this unit.br- Private washer/dryer in unit.br- Guests must be 25 years of age or older to reserve this property.brbrCheck in time is 3:00PMbrCheck out time is 11:00AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

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$332.62

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Private Vacation Home

**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrDOCKSIDE DAYDREAMS is a tastefully decorated villa located in the Coconut Mallory Resort & Marina with two large community pools with plenty of chaises. There are boat slips available on-site for rent if you want to bring your boat.brbrTHE LIVING AREA...brbrThis modern home has just undergone a complete renovation to a very high standard. No expense was spared to make DOCKSIDE DAYDREAMS the best vacation home possible. The huge Smart TV in the living room is perfect for those evenings when you just need a break from all that Key West has to offer. The sofa converts to a queen bed for extra guests, and there’s a full bathroom on the first floor. The fully equipped kitchen has top-of-the-line stainless steel appliances and all of the tools the chef in your group will need to prepare a meal. The kitchen bar will seat four when you decide to stay in, and an outdoor dining set on front porch is perfect for a balmy tropical dinner.brbrTHE ACCOMMODATIONS...brbr** First Bedroom: Located on the Second Floor with a King bed, a large flat screen TV, and an en suite bathroom with a walk-in shower. brbr** Second Bedroom: Located on the Second Floor Two Twin beds OR One King bed, a flat screen TV, and access to the first-floor bathroom.brbrTHE COMMUNITY POOL & GROUNDS...brbrCoconut Mallory is a waterfront private community that provides resort-style amenities, including two large pools, Jacuzzi, BBQ grills, picnic tables and much more. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also an oversized Jacuzzi and a picnic area with BBQs available for guest use.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Smart TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Community Pool Accessbr** Community Jacuzzi Accessbr** Additional Parking Space available for $25 a day or $150 for the week - paid directly to the Property Office on sitebr** Picnic areas with BBQsbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.

Bed

Bath

Sleeps

$436.21

/ Nightly

Private Vacation Home

**MARINER’S HIDDEN HAVEN @ KEY HAVEN** Waterfront Home & Pool + LAST KEY SERVICE

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrEscape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout and coastal décor are the perfect complement to the sun worshipper’s playground outside. Combined with Last Key Realty's Five-Star Guest Services, MARINER’S HIDDEN HAVEN will remind you the importance of treating yourself to an escape from reality.brbrTHE LOCATION…brbrLocated at Mile Marker 5, Key Haven is a highly coveted residential neighborhood. The location has a great balance between a secluded community yet only a short drive or Uber ride to the heart of Old Town Key West. Stock Island has plenty to offer if you don’t feel like venturing into Key West proper; you can dine at Stock Island’s famous Hogfish Bar & Grill, Roostica Pizzeria or Chico's Cantina. You can take in a round of golf at the Rees Jones designed golf course or get out on the water via paddleboard, jet ski or private fishing charter from Hurricane Hole Marina.brbrTHE LIVING AREAS & KITCHEN…brbrMARINER’S HIDDEN HAVEN is a one-story home that offers an open floorplan with a spacious living room, separate TV area, and a beautifully renovated kitchen. There’s plenty of seating for your crew to gather in the living room for a game night or to watch your favorite show on the large flat screen TV. Directly off the living room is a home office space in case you need to work during your stay.brbrThe separate TV area is perfect for extra privacy (or when the group can’t agree on what to watch) and features comfortable seating options. The sofa pulls out to a Queen sleeper to accommodate 2 extra guests. The beautiful kitchen is fully equipped with every appliance and tool needed to prepare meals from home. The indoor dining table seats six comfortably.brbrTHE BACKYARD, POOL, & DOCK…brbrHidden behind a privacy fence and lush tropical landscaping, the backyard and pool area will undoubtedly be a primary gathering place for your group. Spend your days floating in the private pool, which can be heated OR chilled to your liking. Or soak up some sun in the poolside chaise lounges while listening to your favorite island tunes courtesy of the outdoor sound system. The outdoor shower is perfect for rinsing off after a day on the water or after the pool. Under the covered patio you’ll find a full outdoor dining set and mini fridge, plus a propane grill for cooking your fresh catch. You can practically live outside all month! brbrYou’ll also be able to keep your boat docked right out back on the 60' concrete seawall equipped with dock posts, cleats, and dry storage. The air-conditioned shed offers a versatile outdoor space to store your fishing and diving gear, as well as all the items you’ll need for beach or boat days. In addition, this rental home includes 2 kayaks with paddles.brbrTHE ACCOMMODATIONS…brbr** Master Bedroom: King bed, flat screen TV, and closet.brbr** Second Bedroom: Two Twin beds OR One King bed, flat screen TV, and closet.brbr** Pool House: Full sized Trundle Bed and flat screen TV.brbrThere are 2 full bathrooms in the main house - one with a walk-in shower and laundry, and the other with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE: brbr** Washer and Dryer br** Central Heat and A/C br** Ceiling Fans Throughoutbr** Flat Screen Cable TVs in Living Room & Bedrooms br** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels provided br** Wireless high-speed Internet access and full cable is included br** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list: brbr** 60’ of Seawall / Boat Dockagebr** Propane BBQ Grillbr** Private Heated Poolbr** 2 Kayaksbr** Outdoor Sound Systembr** Outdoor Showerbr** Queen Sleeper Sofabr** Off-Street Parking for 1 CarbrbrOther notes: brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings available br** This property will accommodate up to 6 adultsbr** Small Dogs Allowed - Max of 2 dogs and an additional fee of $200 per pet will apply

2

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2

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8

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