Vacation Rentals By Owner In Key West, FL

City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to The Pinder House – where modern comfort meets historic charm in the heart of Old Town Key West! brbr brbrThis beautifully updated historic “Eyebrow” home offers the perfect blend of Key West nostalgia and vacation convenience. Located just steps from world-famous Duval Street and the Historic Seaport, The Pinder House puts you right in the middle of the island’s best dining, nightlife, and attractions — while still offering a peaceful retreat when you’re ready to relax. brbr brbrSpend your days lounging by the private heated/chilled pool, perfect for refreshing dips after a day of exploring or relaxing under the Key West sun. Start your mornings with a cup of coffee or unwind in the evenings with a cocktail on the inviting front porch — the ideal spot to watch the world of Key West go by. brbr brbrInside, the home has been thoughtfully updated with modern amenities while preserving its unique character. Enjoy relaxing living spaces, a fully equipped kitchen, and comfortable bedrooms designed for restful nights after your island adventures. brbr brbrWhether you’re exploring historic landmarks, indulging in fresh seafood, or simply soaking in the laid-back island lifestyle, The Pinder House is your ideal home base. brbr brbrBook your Key West getaway today and experience the charm, comfort, and luxury of The Pinder House! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1 (1st Floor): Queen Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (2nd Floor): Queen Bed brbr brbrLiving Room: Sofa with Pull Out Queen Bed, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely Equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Chlorine Pool (heated to ~85 degrees Nov-Apr, chilled to ~85 degrees Jun-Aug) brbr brbr- Private Outdoor Patio With Seating brbr brbr- Washer/Dryer brbr brbr- Nespresso Machine, Drip Coffee Maker, Toaster, Blender brbr brbr- Linen's and Towels Provided brbr brbr- 3 blocks to Duval Street brbr brbr- 0.7 miles to Mallory Square Sunset Pier brbr brbr- 0.9 miles to Key West Historic Seaport brbr brbr- 0.9 miles to Southernmost Point brbr brbr- 0.9 miles to Fort Zachary Taylor State Park Beach brbr brbr- 2.6 miles to Smathers Beach brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. 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 brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. 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 our guests and property, one exterior security camera monitors the front door. This camera is for security purposes only and does not monitor any private interior or outdoor living spaces.

The Pinder House: Historic Charm w/ Heated/Chilled Private Pool, Steps from Duval St & the Seaport

Key West, Florida, United States

Bed

Bath

6

Sleeps

$313.89

This listing is for a room within a hotel.brbr✦ Your room is 200 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pets are welcome with an additional charge of USD 50.00 per night, with no restrictions on size or breed.

Hotel

Old Town Key West Hideaway with Poolside Fun!

Key West, Florida, United States

1

Bed

1

Bath

Sleeps

$313.88

This listing is for a room within a hotel.brbr✦ Your room is 240 sq. ft, equipped with complimentary toiletries, standard quality TV, available with Standard cable.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 18 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool is available, opened from 7:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $45.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Pets are welcome with an additional charge of USD 50.00 per night, with no restrictions on size or breed.

Hotel

Peaceful Key West Lodge with Outdoor Swimming Pool and Near Attractions

Key West, Florida, United States

Bed

Bath

Sleeps

$785.76

Elegance. Sophistication. Perfection.brbrWelcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Key West. Located on the picturesque and coveted William Street, this extraordinary residence embodies timeless charm, architectural grace, and modern luxury — a rare gem that truly stands apart.brbrBuilt in 1866, this iconic conch-style home was originally owned by the youngest son of prominent Bahamian settlers. With each ownership, the property has been meticulously restored and thoughtfully enhanced, preserving its historic footprint while seamlessly blending in tasteful, contemporary upgrades.brbrRecognized with architectural awards and revered as one of the most exquisite homes in the Key West Historic District, the Gideon Lowe House invites guests into a world where heritage meets comfort in the most elegant fashion.brbrPROPERTY HIGHLIGHTS:brbr- 3 Bedrooms | 3.5 Bathroomsbrbr- Award-Winning Historic Homebrbr- Original Dade County Pine Throughoutbrbr- Private Pool with Waterfall & Sun Deckbrbr- Off-Street Parking (1 space)brbr- Fully Fenced Front & Rear Yardbrbr- Prime Old Town Location – 4 Blocks from Duval St.brbrINDOOR FEATURESbrbrMain Floor:brbr- Expansive sitting porch & welcoming foyerbrbr- King guest suite with walk-in closet, flat-screen TV, and luxurious en-suite bath (tub & shower)brbr- Stylish powder roombrbr- Chef’s kitchen with premium finishesbrbr- Formal dining room ideal for entertainingbrbr- Spacious living room & back entertainment loungebrbr- Lush outdoor sitting area, private pool with waterfall, sun deck & loungersbrbrSecond Floor:brbr- Dedicated laundry room & office/landing areabrbr- Lavish primary suite with king bed, flat-screen TV, oversized walk-in closetbrbr- Spa-inspired bathroom with soaking tub & walk-in showerbrbr- Private balcony with cozy seatingbrbrThird Floor:brbr- Charming third bedroom with two twin bedsbrbr- Full bathroom with walk-in showerbrbr- Generous closet spacebrbrLOCATION, LOCATION, LOCATION: brbrNestled in the desirable Historic Seaport District, this home is just steps away from the very best of Key West — world-class dining, galleries, shops, and entertainment. Only four blocks from Duval Street, yet tucked away in a quiet residential enclave, the Gideon Lowe House offers unmatched convenience with serene privacy.brbrYOUR STAY:brbrWhether you're seeking a tranquil escape or a stylish base for island adventures, this remarkable residence delivers beyond expectations. From its storied past to its curated interiors and luxurious amenities, every detail has been designed with your comfort and experience in mind.brbrDon’t miss your chance to stay in one of the most captivating homes in Key West — where history, elegance, and tropical splendor come together in perfect harmony.

The Gideon Lowe House - Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$611.19

Welcome to The Secret Grotto — Your Luxurious Tropical Escape!brbrStep into this stunning 3,220-square-foot sanctuary nestled on nearly 5,000 square feet of lush, private paradise. This spacious Key West retreat boasts 3 oversized bedrooms, 4 full bathrooms, and an entertainer’s dream layout designed for unforgettable moments with family and friends.brbrInside, be wowed by the chef’s kitchen—gleaming with top-of-the-line Viking appliances including a 48-inch gas range, built-in steamer, wine cooler, and rich Cherry cabinetry—perfect for crafting gourmet meals or casual island snacks. The open-concept living and entertainment area flows effortlessly, ideal for relaxing or hosting lively gatherings.brbrStep outside through two grand sliding doors to your own tropical oasis. Lounge by the expansive lagoon-style pool complete with a mesmerizing grotto waterfall, or unwind on sun-kissed loungers and dine alfresco with seating for eight under the open sky. Private, fully fenced, and inviting—this backyard paradise is your personal slice of island heaven.brbrUpstairs, discover three sumptuous en-suite bedrooms designed for ultimate comfort and privacy. The primary suite pampers you with a king-size bed, cozy sitting area, smart TV, a private balcony overlooking the pool, and a spa-inspired bathroom featuring a jacuzzi tub, dual vanities, and a spacious walk-in closet.brbrTwo additional guest suites offer king and queen beds, elegant sitting areas, smart TVs, and luxurious bathrooms with walk-in closets, ensuring every guest feels right at home.brbrAdditional amenities include a two-zone HVAC system for perfect climate control, impact windows and sliding doors for tranquility and safety, plus secured off-street parking for two vehicles.brbrLocation is everything: Situated in vibrant Mid-Town Key West, you’re just minutes from pristine beaches, iconic landmarks like the Southernmost Point, Mallory Square, the buzzing 200 Block of Duval Street, and a variety of top-notch dining and nightlife options. Whether you prefer a vehicle or golf cart, everything you want is within easy reach.brbrBonus: Heat your private pool during cooler months (November 15 - May 1) for just $20 per day—perfect for year-round luxury.brbrThe Secret Grotto is more than a vacation home — it’s your personal island retreat, combining spacious elegance, upscale finishes, and unbeatable location to create a getaway you’ll want to return to again and again.

The Secret Grotto

Key West, Florida, United States

Bed

Bath

Sleeps

$275.79

OLD TOWN PARADISE....brParadise awaits in a cozy Truman Annex retreat. Set on a cozy lane that is off the beaten path but close enough to walk or ride your bicycle to restaurants, this unique gem offers your much needed tropical R&R!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brEnter this sparkling, cozy abode through the front gate where a small porch with seating invites you for morning java and sultry island breezes. As you enter, a fully-equipped kitchen greets you which includes an electric stove, microwave, refrigerator, coffee maker, toaster oven, and kitchen bar area. Gather, drink and dine around the dining table for 4, then settle in the adjacent living room on your cozy sofa (pulls out as a sleeper) or cushioned chair and enjoy movies on a large flat-screen tv. Two sets of french doors welcome in the warmth and sunshine of tropical living and open to your private patio with grill and outdoor seating for 4. A convenient powder room is also located in the living area.brbrSLEEPING ARRANGEMENTS...brTravel up the stairs to two en-suite guest rooms when you're ready to rest and refresh for the next day's adventures. The primary bedroom features a king bed with dresser, small flat screen tv, a large closet for storage and hanging clothes and also includes a make-up vanity, ironing board, and iron. The private bathroom is equipped with a glass-door shower and sink cabinet with storage drawers. Open your french door to your own enchanting small terrace with two chairs and a table for quiet conversation or a date with your favorite novel. Walk down the upstairs hallway to the second bedroom which features a queen bed, flat screen tv, storage closet for hanging clothes and an additional dresser inside. The private bathroom offers a shower/tub combination and sink cabinet with storage drawers. The washer/dryer closet sits between the two bedrooms in the upstairs hallway.brbrOUTDOOR LIVING...brWalk through the living area french doors to your private outdoor area with seating for 4 and a gas grill, which is the perfect cocktail spot or for dining under the twinkling stars. Take a stroll through this attractive community which is just right around the corner from Fort Zachary Taylor State Park, Harry Truman’s Little White House and Truman Annex’s Waterfront Park. Swimming in the heated community pool is a great way to wash off the day and it's just around the corner from the unit. There is a cabana with restrooms in the pool area and plenty of lounging chairs for your sunbathing pleasure.brbrPARKING...brThis home does offer covered parking for one vehicle. No vehicle length over 18’ long, including trailer hitches, or 80” wide is allowed on property.brbrPETS...brThis is not a pet friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPet fee (if applicable)brbrBOOKING DATES...brThis home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$617.63

The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, dining area, a luxurious kitchen, and two bathrooms. It can accommodate up to six people, two in each of its two bedrooms and two additional persons on a convertible sofa in the living room. Book a Key West getaway today!brbr* 1 King, 1 Queen, 1 Queen Sleeper Sofabr* 2 Full Bathroomsbr* Sleeps up to 6 Peoplebr* Continental Breakfast Includedbr* Full Kitchen with Dining Areabr* Shared Pool Deck and Private Balconybr* Flat Screen TV with Cablebr* Parking by Reservation ($15/night plus tax)br* 200 Feet from Duval Street

Villa

Two Bedroom Two Bath Balcony Villa Steps from Duval!

Key West, Florida, United States

Bed

Bath

Sleeps

$405.05

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in Key West. Best of all, Casa Atlantica is located just a short bike ride from Duval Street and the Historic District, so you get the peace and quiet of the tranquil shore without sacrificing access to Key West’s unsurpassed restaurants, shops, and attractions.brbrOpen the door to this property and you are welcomed by an entire wall of floor-to-ceiling windows, giving you unrestricted access to the most breathtaking view in the Keys. Slip outside on to the large, private patio and enjoy the warm sunshine and salty breeze of the natural shoreline. Playful pelicans and majestic egrets swoop and dive into the cobalt-blue water directly in front of you! This is true coastal living at its best.brbrThe large patio doors can be left open to allow the ocean breeze in to the spacious, comfortably furnished living area, which features a flat panel television and a sizeable dining area with a wet bar. Down a short hallway is the fully equipped kitchen with a glass-top range. The large, unique bathroom includes conveniently separated areas for the sink and commode, as well as a massive tub for soaking. The tranquil bedroom contains a king sized bed and heavy drapes for those mornings you want to sleep in. Another patio can be accessed from both the bathroom and bedroom areas. The entire home features distinctive, Adobe-style rounded walls with built-in furniture and charming brick tile floors. The whitewash walls reflect the lovely natural light and create an effect that is fresh and soothing to the senses.brbrIf you want to put your toes in the sand, head downstairs to the charming tiki hut right by the water. This property also has a shared washer and dryer and limited street parking. Please be aware that this unit is accessible only via 2 flights of a centrally located staircase.brbrIf you are dreaming of a vacation by the shore, it just doesn’t get any closer than Casa Atlantica!brbrBedding: 1 Kingbrbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the summer. This is a natural phenomenon that is outside of our control.

Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$235.38

Stunning open water views from this beautiful oceanfront home. You can enjoy quiet mornings and spectacular sunsets.brbrThe home features 2 bedrooms and 2 bathrooms. The master bedroom is equipped with a king size bed, and attached master bathroom. The guest bedroom is furnished with a queen size bed. Second bathroom can be accessed from the main living/kitchen area, as well as from the guest bedroom hallway. There is a limit of 2 pets only. brbrThis home has a fully equipped kitchen/dining area sitting for 6, as well a spacious living area, with a queen size sofa sleeper and a big screen TV. Just exit the living room, and you can enjoy spectacular views from the upstairs patio overlooking the Atlantic Ocean.br brGuests have full access to both Atlantic and Gulf from our 44 feet seawall.brbrThe downstairs area is covered, and includes a dining table and grill, where you can cook your fresh catch. There is also covered parking for 2 cars. You can explore the beautiful bay area from the home using the 2 kayaks provided. brEnjoy a day out in the sun on one of the 4 lounge chairs or watch the unique sunset from the lower level concrete patio by the water, also have a glass of wine in our TIKI HUT and enjoy the view!brbrThe neighborhood has a large community park with tennis courts, basketball, playground and a large field. It is also within walking distance to the world-famous Baby’s Coffee shop.brbrThis home is located only 10 minutes to beautiful island of Key West. Come and see what the Florida Keys have to offer!!! br

Oceanfront Paradise! (15 minutes from Duval)

Key West, Florida, United States

Bed

Bath

6

Sleeps

$556.88

This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It features a fantastic, fully equipped kitchen with new cabinetry and granite countertops, dining room, living room and a very spacious master bedroom & bath. This suite will sleep 5, with a king bed and a twin pullout in the master bedroom and a queen pullout in the living room. Also, one of a kind, is the huge deck with an outside table & chairs, private hot tub and a spiral staircase to a private rooftop deck for fantastic views of all of Key West. For added convenience, this suite offers 2 TVs with cable, DVD players, washer/dryer, iron & ironing board, free wireless internet and a safe..

Galleon Resort beach hotel luxury in Old Town Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$457.6

Home of Famous Ernest Hemingway and Jimmy Buffet. Enjoy the downtown area on Duval Street where Sloppy Joe's and Captain Tony's bar are located. .Hemingway House greets thousands of visitors to experience the 6 toe cats living on the property. The Ole Light House Museum across the street is a highlight. A tropical boater's and angler's paradise boasts the best fishing and weather in the country. With tangerine sunsets glistening across the calm Atlantic and Gulf of America. An afternoon boat ride is just a perfect way to end your day. Pulling up to the docks at the famous sunset activities gathered on Mallory Square daily. Dolphin, turtle and fish sightings are possible in the turquoise waters of the keys. Lovely views from the balcony to enjoy the beautiful private outdoors. Smart TV and internet available.brbrKitchen utensils, dishes, and linens are plentiful. brbrFamily oriented community with pool/BBQ. Quiet private yard with parking. Beautiful grounds to entertain by the pool.

Charming Key West Town Home Beach/Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$390.06

PERFECT TROPICAL POOL RETREAT…brIf you've been searching for the ideal island getaway, look no further. This classic Key West jewel is precisely what your island soul has been yearning to find. This quintessential tropical nest beckons you inside its private gated entrance, where sumptuous living and sultry breezes collide in a perfect storm of blissful pleasure. Tucked into the quiet neighborhood of Midtown, you are close to pristine beaches, White Street Pier, bustling restaurants and a short bike ride to famous Old Town.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brStep inside this oasis where you are surrounded by a privacy fence that encompasses lushly landscaped front and back yards. The serene refuge of this home offers respite after a day of adventure under the southernmost sunshine. Craft your icy cocktail in the modern, fully-equipped and beautifully updated kitchen with a gas range and under counter beverage fridge, then ease onto the cozy furnishings in the adjacent living room and relax with your favorite tv show, a good book or dive into a board game together. The spacious dining room is a perfect setting to share stories over delicious cuisine with your friends and family. This home is equipped with wall mounted Roku enabled SmartTVs in every room and free WIFI. throughout. A washer/dryer is available for your convenience as well. brbrSLEEPING ARRANGEMENTS...brAll of the 4 bedrooms (to include the one in the pool house), offer smart TVs and cooling ceiling fans. The main house features a king bedroom, a queen bedroom and a twin bedroom that can convert to a king bed upon request. The king and queen rooms have desks and a laser wifi printer for those working remotely. The bedroom in the pool house offers twin beds that can also convert to a king (shown as King in photos). Both glass walk-in showers reside in the main house. brbrOUTDOOR LIVING...brThe impressive backyard oasis is a focal point of this spectacular island gem, boasting a sparkling heated pool, al fresco dining table for 10 and seating with sail shade, large propane grill, cooling outdoor shower, cafe table with seating, and pool loungers. It all adds up to an exquisite day under shaded palms and healing sunshine. Sway on the front yard hammock or hop on of of the 5 beach cruisers so you can stroll the charming lanes of Key West to the nearby Pickleball and Bocce courts!brbrPARKING...brThere is off street parking available for this home.brbrPETS...brPets are considered at this home and a pet fee is required. Please include the size/breed when inquiring. brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refund. brbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrTHIS IS YOUR HAPPY PLACE...

BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$354.65

SUMMER SPECIAL PRICING NOW AVAILABLE — INCLUDING SELECT TWO-NIGHT MINIMUM STAYS!brbrTake advantage of reduced summer rates and enjoy a relaxing Key West getaway at Sunrise Condo — the perfect home base for your island vacation.brbrThis spacious two-bedroom, two-bath condo comfortably accommodates up to six guests. The primary bedroom features a king bed, the second bedroom includes a queen bed, and the living room offers a queen-size sleeper sofa for additional sleeping space. For added comfort and entertainment, all bedrooms as well as the living room feature flatscreen smart TVs.brbrAfter a day at the beach, exploring Old Town, or enjoying Key West’s restaurants and attractions, cool off in the sparkling community pool or relax in the hot tub. Inside the condo, you’ll find a comfortable living area with flatscreen TV and free high-speed WiFi, along with a fully equipped kitchen perfect for preparing meals at home. A private covered parking spot is also included — a valuable convenience in Key West.brbrSunrise Condo is family-friendly and dog-friendly. A Graco Pack 'n' Play with sheet is provided at no charge, and additional baby equipment rentals are available locally. One well-behaved dog up to 25 pounds is welcome with payment of a pet fee.brbrPool Safety Notice:brThis property features a community pool. There is no lifeguard on duty. Guests swim at their own risk, and children must be supervised by an adult at all times while in or near the pool area. By booking this property, guests acknowledge the inherent risks associated with pool use and agree to exercise appropriate caution and supervision.brbrPlease note: All cancellations are subject to a cancellation fee, which varies depending on the cost of the reservation.

Key West Sunrise Condo - SPECIAL SUMMER RATES!

Key West, Florida, United States

Bed

Bath

Sleeps

$709.5

Discover the charm and grace of Old Key West in a new and distinctive setting. Luxury, two-bedroom, two-bath, waterfront condominium set in a topical garden paradise with sweeping balconies overlooking the Atlantic Ocean. Your vacation hideaway is decorated in authentic island tradition with fully-equipped modern kitchen, living room with wet bar, and dining room. Washer/dryer, phone, TVs, stereo, and over-sized jacuzzi tub in the master suite.brbrYour bit of paradise features a lush tropical garden complete with an Olympic-size, oceanfront, heated pool, and sun deck with adjacent bubbling whirlpool. Balmy Caribbean breezes caress you from your sweeping balcony. For your sporting pleasure, there are three lighted tennis courts (one which is clay), racquetball courts, and pro shop. Your condominium has a unique barbecue/picnic area, and features 400 feet of private frontage adjacent to Smathers Beach. Also available is a private slip that can accommodate 30' boat. brbrbrOff Season specials: please contact us for these and other specials

Oceanfront

Key West, Florida, United States

Bed

Bath

Sleeps

$2032.11

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrTHE DUKE & THE DUCHESS is a compound fit for a Queen, her King, and their whole court! These newly built, professionally designed side-by-side homes have everything you could desire for a large group vacation - a prime location, coveted amenities, and plenty of space. Your stay at the THE DUKE & THE DUCHESS also includes Last Key Realty's Five-Star Guest Services & Complimentary Concierge, ensuring you’ll receive 'the royal treatment.'brbrTHE LOCATION…brbrIf you decide to pull yourself away from these beautiful homes, you’ll realize that the best Key West restaurants, live entertainment, and attractions are all within a few blocks of your front door. While you won’t need a car to get around from this fabulous location, there are two off-street parking spaces in the driveways. If you don’t have vehicles but want to explore the island in a fun way, Last Key Realty’s concierge service can assist with golf carts, scooters or bike rentals.brbrTHE LIVING AREAS…brbrEach home features an open and spacious living area. There are large flat-screen Samsung Frame TVs in each living room watchable from the large, plush sofas, which pull out to a queen sleepers for extra guests. The open floor plans seamlessly flow between the living areas and the kitchens, creating even more open space. Both homes offer fully equipped kitchens with every appliance and tool your chef will need, as well as large dining tables with room for the entire royal court to feast.brbrTHE BACKYARDS...brbrTHE DUKE & THE DUCHESS each have a private, fully fenced backyard that connect via a lockable gate. The backyard of THE DUKE features a propane grill, an outdoor dining table, and a spacious hot tub. The backyard of THE DUCHESS features a propane grill, and outdoor dining table, and a private heat-optional pool.brbrTHE ACCOMMODATIONS…brbrTHE DUKEbr** Sunset Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Ocean Suite: Located on the Second Floor with Two Twin beds OR One King bed, a flat-screen TV, a built-in armoire, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbr** Queen-sized sleeper sofa in the living roombrbrTHE DUCHESSbr** Florida Suite: Located on the First Floor with a King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Paddleboard Suite: Located on the First Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Media Room: Located on the First Floor with a sofa that pulls out into a Queen to accommodate extra guests and a flat-screen TV.brbr** Whale Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a built-in armoire, and an en-suite bathroom with a walk-in shower.brbr** Flamingo Suite: Located on the Second Floor with Two Twins OR One King bed, a flat-screen TV, a closet, and an en-suite bathroom with a walk-in shower.brbr** Aviary Suite: Located on the Second Floor with a King bed, a flat-screen TV, a closet, a trundle bed with two twin mattresses, and an en-suite bathroom with a walk-in shower.brbrNeed even more space Add QUEEN OF LOUISA, a 4 bedroom private home, which connects through the backyard of THE DUKE!brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Rooms & All Bedroomsbr** Fully-Equipped Kitchensbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** 2 Fully Fenced Yardsbr** Private Pool (with heat available)br** Private Hot Tubbr** 2 Propane BBQ Grillbr** Off-Street Parking for 2 Vehiclesbr** 2 Queen Sleeper SofasbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 22 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per petbr** 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.

**THE DUKE & THE DUCHESS @ DUVAL** Compound w/ Pool & Hot Tub + LAST KEY SERVICE

Key West, Florida, United States

Bed

Bath

Sleeps

$815.63

Concierge Realty is proud to present luxury villas at Hyatt Windward Pointe!brbr**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.brbr**All bookings are time sensitive and availability can change at any time. Send us a message to confirm exact availability prior to making a booking request. brbrSet along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale resort ambiance. Here is a retreat where you can slow down and forget the rush and stress of your day-to-day life.brbrThis ultra-spacious, ultra-plush two bedroom at Hyatt Windward Pointe features a master bedroom with a king bed and master bath outfitted with a walk-in shower and spa tub, and the guest bedroom with a queen bed. Enjoy the convenience of having a full kitchen, dining area, living room, TV, fully-furnished balcony and complimentary Wi-Fi access!brbrBask beside the lushly landscaped pool that gives you the illusion that you’re softly floating on the open sea, grab a snack at Abbey Road poolside sandwich and snack bar or get your blood pumping at the fitness center at site resort Hyatt Key West Resort & Spa.brbrComplimentary self-parking is available at the resort. No recreational vehicle parking is permitted. No valet parking is available. Tesla and electric car charging stations are available. Boat and trailer parking is available at $25 plus tax per night and must be booked in advance by calling the front desk.br brbrThe Vrbo calendar helps provide availability and estimated price quote. Always inquire with the agent and do not reserve airfare until your confirmation has been received.brbrAny issues with resort service, accommodations, physical plant, amenities, etc. are the direct responsibility of the developer and must be handled through the resort, not Concierge Realty. Photos are thought to be truly representative of the resort and accommodations. Any variation from the photo and actual property are unintentional, so guests are encouraged to do their own due diligence prior to reserving. Any variance or disruption including but not limited to renovation, unavailable amenity, change in decor, etc. during the stay, whether announced prior to reservation, occurring during the stay or announced after confirmation, is a matter strictly between the guest and resort, are not deceptive advertising, breach of contract or the responsibility of Concierge Realty.brbrNote that the images are representative of this villa and that a specific view type is not implied nor promised by virtue of the images. A specific view category must be addressed with rental agent. Concierge Realty reserved the right to reserve any view category unless one has been agreed upon in writing. The resort confirmation will show the view designation and the villa will be placed within that view category unless, in a rare instance the view will be noted as not guaranteed in which case the resort reserves the right to place the guest anywhere within the property. Issues regarding view within the guaranteed view category are to be addressed with the resort management as Concierge Realty is not responsible for villa placement.brbrPlease be advised that if a non-domestic credit card is used to reserve a vacation rental, additional fees may be incurred.brbrAll details are accurate to the best of our knowledge. Any questions with regard to view, amenities, bedding configuration, decor or other details should be addressed with Concierge Realty, Winter Garden, FL.brbrGuests are encouraged to do their own due diligence to assure that the resort and villa will meet their expectations.

Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Book now!

Key West, Florida, United States

Bed

Bath

Sleeps

$303.91

In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard Condominium has great access to Fort Zachary Taylor State Park Beach as well as the Historic Old Town Key West. This beautifully decorated first floor condominium on Southard Street has two bedrooms, one full and one half bathrooms. brbrThe living room is nicely furnished with leather sofas, tv with DVD and high speed internet along with a fully equipped kitchen and dinette area to accommodate four people. One bedroom has been upgraded to a king bed, while the front bedroom has a queen bed. A large back deck gets ample sun and just enjoy the Key West weather. The association pool is just a short distance away. brPLEASE NOTE THERE IS NO GRILL.brTHE POOL WILL BE CLOSED FOR THE MONTH OF AUGUST, 2026.brbrBedding: 1 King, 1 QueenbrbrThere is one reserved parking space in a gated lot.

Reduced Pricing!!! A Slice of Paradise! @ the Shipyard Palms!

Key West, Florida, United States

Bed

Bath

Sleeps

$421.86

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. Both bathrooms have recently been remodeled and a private laundry is located in the unit.brbrThe quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, and Hog's Breath as well as a plethora of delicious restaurants. Venture just a short distance further to Mallory Square or the famous Historic Seaport. It's easy to see why this location is unbeatable. The shared compound, of 6 total homes, features a winding brick pathway surrounded by tropical foliage and flowers that lead to a free form heated pool tucked away in the far side of the gardens. Take a refreshing dip, lounge and catch some sun, or enjoy a good book while being surrounded by beautiful trees and plants. This truly is a relaxing outdoor oasis!brbrUpon entering Ann Street Cottage you'll feel refreshed by the cool and relaxing decor. Neutral colors combine with pops of tropical color throughout to create an inviting atmosphere to relax in. Lounge in the living room while reading a great book or catch the morning news. Transom windows let in light and the vaulted ceiling creates a bright and airy atmosphere. A small dining table for two sits just off the fully equipped clean white kitchen. A half bathroom is conveniently located next to the kitchen. The bedroom combines island charm with boutique hotel style complete with full ensuite bathroom. Calming hues and pops of coral and teal will lull you to sleep after a busy day of exploring the island. French doors open out to the private patio with outdoor dining table from the bedroom and living room. A small office space with desk and chair are located behind the patio, in case you must get some work done. The washer and dryer is in this office space as well.brbrAnn Street Cottage combines a peaceful hideaway with excellent location making it the perfect option for a couple looking to have the ultimate Key West experience. brbr(The Ann Street Compound Homeowners Association requires all occupants to be 16 + yrs. Regretfully, NO Children under 16 are allowed. This home is also not pet-friendly) STREET PARKING ONLYbr brBedding: 1 king bed

Cottage

Ann Street Cottage: A bright and airy home near Duval Street

Key West, Florida, United States

Bed

Bath

Sleeps

$420.43

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly opposite Smathers Beach. La Brisa offers a neighborly and relaxing atmosphere. Join in on community held activities at the club house, play in a match on the tennis courts and enjoy the sizable pool, hot tub and a spacious common area for chatting, eating and lounging in the sun.brbrMake your vacation memorable and relish in the comfort and beauty of The Sea Orchid. This recently renovated condo features two bedrooms, two bathrooms and a magnificent view of the ocean. The open air design of the living/dining area adds to the spaciousness. While looking out over the Atlantic Ocean, recline on your sofa or rock yourself in your wicker rocking chair and take in the colors of a Key West sunset. The recently renovated kitchen is roomy and boasts a stainless steel refrigerator, and double sink. The large glass dining table has room for six a great view of the ocean.brbrThe primary bedroom offers a king bed and double windows looking out over the ocean and a fabulous walk in closet/dressing room. The spa-like primary bathroom has dual vanities and an oversized, glass-enclosed walk-in shower. This bedroom also has its own individual access to the private balcony, perfect for an early morning cup of coffee and a sunrise. The second bedroom has two twin beds and a large closet boasting lots of storage. The second bathroom is stylish with its modern glass and tile shower, full wall mirror and granite topped vanity.brbrLa Brisa captures a feel for island life, the way the locals live it, away from the clamor of down town. Quiet moonlit walks on the beach, a morning café con leche from a local vendor and a beach sunrise make for an unforgettable vacation. And while you are tucked away from the noise, you are not too far away. There is a bike trail that leads you along the Atlantic Ocean, past many Key West sights, into the down town area. A large selection of fantastic Key West restaurants and attractions are just a pleasant bike ride away.brbrBedding: 1 King and 2 Twins.brbrThere is elevator access from the ground floor to the condos above. There is one reserved, covered parking space.brbr**ELEVATOR SHUT DOWN NOTICE: The East building elevator will be shut down starting April 27th, 2026 until April 25th, 2026 for a Elevator Modernization Project. The condo will ONLY be accessible via stairway.brbr**POOL CLOSURE** The pool and jacuzzi will be closed from July 6th to August 30th. brbrPlease note; the LaBrisa Condo Association requires additional registration in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr**Disclaimer**brbr*The peak sargassum season in Key West is typically from July thru September, with June may also see significant amounts which can impact your stay. While the naturally occurring seaweed itself is not dangerous, it can accumulate on beaches, producing a foul odor and potentially harboring organisms that cause skin irritation. We do not provide discounts for the situation.

Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)

Key West, Florida, United States

Bed