Vacation Home Rentals By Owner In Key West, FL

`In-the-know` travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia`s Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval, and because it is all the way at the end of an unknown lane it is well hidden from public view. Unless you`ve stayed in this villa before, there`s no-way you`d ever know it`s just steps off Upper Duval Street in one of the prettiest parts of Old Town Key West..brbrThe property itself is authentic Key West and unique all-the-way. Pineapple carvings on the fence gracing this property just hint at the island-living charm you find inside. Art work by famous local Caribbean folk artist David Wegman perched above the gates welcomes you at the entrance. Enter the large wooden blue-green gate off the little private lane and you step into the beautiful courtyard with a crystal clear swimming pool. A statue of the happy Buddha graces the pool side and further welcomes you to your home in Key West and once inside the courtyard you are treated to even more art work; this time canvas art pieces painted by the late Key West artist Sanford Birdsey are uniquely incorporated into the courtyard walls.brbrThe layout of this vacation villa was re-worked in October 2008 by local designers to maximize comfort and sleeping options that now include four full bedrooms that all open to the private courtyard. The room layout features one spacious great-room with open kitchen / living room and a flat screen HD TV. The great-room opens directly to a covered lanai that has a dining table for `el fresco` dining.brbrThe best way to visualize the layout of this Amelia`s Hideaway is to consider each room as it is situated within the courtyard. The house is built as an `L-Shaped` villa with each room in the house opening to the courtyard, and then 3/4 of the roof of the villa is an expansive Mexican tiled roof-top deck. We begin our descriptive tour as you pass the rooms once inside the courtyard gates.brbrRoom One: Bedroom #1 (yellow room) is a large room and is set as a full suite offering 2 twin beds that can be put together to make a king size bed and a private full bath divided into two - shower room and powder room with commode and sink. There is also a table conveniently placed for your lap-top. This room also offers a full size sofa that can be made into a queen bed.brbrRoom Two: Bedroom #2 (blue room) has a king size bed. This bedroom connects to a full bathroom with bath tub. The design is decidedly unique and very tropical using tumbled marble in an unusual design.brbrRoom Three: Bedroom #3 (rose room) has a Queen bed and offers a writing desk. While this bedroom connects to the same full bathroom as bedroom #2, the door connecting this bedroom to the courtyard is just steps from the `pool bath` which can be used as a private bath for the `rose room`.brbrRoom Four: The great-room (living room / kitchen) is the fourth room down the line of the courtyard. The great-room has a beautiful retro-style blue and white kitchen that is open to the cream colored living room area on the other end of the room that provides a sofa and love seat. This combined living area has a flat screen HD TV. The sofa in this great-room is a queen sleeper sofa if you need another bed in a private sleeping area. The main dining area for this room is found in the covered lanai just out the French doors from the kitchen offering a Caribbean `el fresco` dining.brbrRoom Five: The `pool bath` is an artistically tiled full bathroom with a blue and white design created by a local Key West artist. This bathroom has entrances from the lanai as well as the `great room.`brbrRoom Six: The sixth room (green room) is Bedroom #4 and is considered the master suite for this villa as it is situated `off to itself` offering the most privacy. This bedroom offers a king size bed and a private full bathroom. The bathroom is tiled in tumbled marble tile of muted tones of golden brown.brbrRoof Top Deck: The next living space in this unique Key West villa is outdoors and upstairs on the large Mexican tiled roof top deck which expands over 3/4 of the roof. This upper deck is reached by a stair case just outside the master suite. The upper deck offers the perfect spot for private lounging, sunning, star gazing, catching the ocean breeze, or staging a roof top cocktail party or dinner. This deck is furnished with outdoor furniture, built-in side bench seating, and outdoor lighting.brbrLaundry: Finally, back towards the entrance gate is a separate building which serves as the laundry and utility area.brbrThe general design of this property lends itself perfectly to small gatherings of families and friends and should be considered an ideal spot for a gathering of family or friends.brbrBedding Summary:brbrbrBedroom #1 - 2 twin size beds (can be made as a king size bed); queen sleeper sofa.brbrBedroom #2 - king size bed.brbrBedroom #3 - queen size bed.brbrBedroom #4 - king size bed.brbrAmenities: Well hidden at the end of little known lane. Private swimming pool, large private gated courtyard, expansive private roof-top sun deck, privacy fences. Fully equipped kitchen, el fresco dining, a/c, telephone, color cable TVs, stereo. Laundry room with washer / dryer. Linens and towels are provided. Designated parking spot at a nearby lot.brbrActivities: Elegant Upper Duval St. - Close to the Southernmost Point of the United States. Cafe neighborhood features art galleries, wonderful eateries and internationally famous fine restaurants, coffee houses, fine gift and clothing stores, Grand Vin wine tasting, Flamingo Crossing home made ice cream. Here you start at the top of Duval St. near the Atlantic Ocean and can take the 20 min stroll to the Gulf of Mexico (remember it takes 3 to 4 Key West streets to equal the distance of a typical city block). Sailing, boating, diving, museums, nightlife.brbrArea: Walk out your gate and down the lane to everything you want to see in Historic Key West. Best restaurants, shops, galleries, clubs, Hemingway House Museum, Light House Museum, Custom House Museum, Key West Aquarium, Butterfly Conservatory, 4 blocks from Southernmost Point of the U.S., close to beaches. Walk everywhere from here.brbrRestrictions: Smoke free house. Smoking permitted outside only. No pets please. We do not accept guests less than 25 years of age unless accompanied by a family group or guardian.brbrPAYMENT: Payment for the rental will be processed outside of VRBO according to the terms of your rental agreement (sent for review upon reservation). Payments by credit card are subject to an additional 2.95% merchant processing fee.brPARKING: Parking is NOT allowed on the lane, directly in front of Amelia’s Hideaway. Please understand that this is designated as a fire lane by the City of Key West. However, you are welcome to use this area for unloading and loading your vehicle when you arrive or bring in groceries.brbrOur company does provide one designated off-street parking spot for you. The lot is located at 600 Amelia St, about 5-minute walk from your property. Your spot is marked with a red sign that reads “521 Amelia.”brbrSince this part of the island was developed before there were cars, parking can be challenging and should be expected. It is best to park your car, remove your valuables, lock up, and forget about it when you are here. Enjoy your location and walk or bike everywhere if possible.

Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool

Key West, Florida, United States

4

Bed

4

Bath

10

Sleeps

$907.82

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.

Waterfront Luxury Home with private pool!

Key West, Florida, United States

4

Bed

Bath

8

Sleeps

$976.0

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$2368.25

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

BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST

Key West, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

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

Southernmost View - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$916.2

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$975.31

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).

Oceanview home with private pool & lush landscaping!

Key West, Florida, United States

Bed

Bath

Sleeps

$332.62

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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$345.44

Enjoy the best of Key West in modern and spacious comfort. This pet-friendly home is within minutes of restaurants, shops, and entertainment venues. This property has two separate residences which allow for privacy and guests. The main home has 1 bedroom, a kitchen, and a living room, plus a loft that could be an office or used as a guest space. The upper apartment has two more bedrooms with a kitchenette, a living room, and a bath. Relax under the palm trees in a large heated pool with sunning shelf.brbrThe spacebrThe home is on a large lot, completely fenced for privacy and security. There's a big yard and plenty of room for kids or pets to explore and play. There's a beautiful pool and shallow sunning shelf.brbrThere are two homes on the property.brbrThe main house is a beautiful and modern one-bedroom with an office loft. The office has a pull-out sofa. The bedroom has a King bed and opens to and overlook the pool area. It has a large bathroom and shower and washer/dryer. There is a full kitchen and living room.brbrThe second home is elevated, above a double garage and has its own living room, a kitchenette, and two bedrooms plus a large bath. One bedroom has a King bed, the other has a Queen adjustable bed. That home has its own porch that overlooks the pool and the main home.brbrThe property is new construction and has all of modern conveniences and luxuries. Pets must be approved, but are welcome. The lot has lots of foliage and palm trees and a great private outdoor shower. There's lot of exterior seating and loungers.brbrLocation: In a quiet neighborhood about 3 miles from Duval Street, on the island of Key West. There is a large garage and a place to park bikes, a boat trailer, a golf cart, and more. We recommend you rent a golf cart for the month or bikes so that you can enjoy the island with ease.brbrGuest accessbrYou have full use of the space. At least one garage space will be available.brbrOther things to notebrPets are allowed, but do need to be approved. Some pets may require additional cleaning fees. The yard is large with lots of room and a very secure fence for dogs.

Modern Luxury with 2-bed Guest Home, Garage and Pool in Key West!

Key West, Florida, United States

Bed

Bath

Sleeps

$436.21

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

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

Key West, Florida, United States

Bed

Bath

8

Sleeps

$326.31

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

Hatteras Sleeps 8 & SelfDrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar

Key West, Florida, United States

Bed

Bath

Sleeps

$294.31

This colorful three bedroom, two full bath, private, and historic home is just 2 blocks from world famous Duval Street! You will be just around the corner to The Hemingway House , famous Blue Heaven Restaurant and the Key West Lighthouse. brOur quiet lane starts on Petronia Street, which has become the culinary center of Key West. VIV wine bar, Le Creperie, Blue Heaven, Rams Head, & Santiago’sBodega are at the end of the road. Our location is simply perfect! Enter your desired dates and click Book Now! Read our 5-Star Reviews! (Please note: We have a 28 night MINIMUM stay. No exceptions can be made.)brbrOwners offer a marvelous home away experience. Three covered porches overlook a breezy tropical paradise with a unique shared 70' lazy river pool. TREETOPS has TWO floors of living. Perfect for your guests to join you in paradise. brbrAll furnishings have a cool, relaxed Key West vibe. The conch-style home was recently remodeled and meticulously furnished to a very high standard with ONLY Rave reviews from our guests. The pictures show accurately how well this SPOTLESS, colorful home SPARKLES. brbrTwo FREE bicycles come with the property and a parking spot option- not that you need it- Key West is a walker's paradise from your perfect location. brbrThe entire second floor is a Master Bedroom Suite with walk in shower, huge closet, and a private covered porch with views overlooking the Key West Lighthouse and our fabulous lazy river pool. Perfect spot for your morning coffee or a cocktail hour. Master suite also offers a private side staircase… easy access to pool. Outdoor teak and mahogany porch furniture, made from reclaimed boats, offers solitude and privacy up on the second level covered porch. Sliding glass doors on the second level overlook tropical grounds -See pictures! brbr Everything you need is right here... new appliances washer/dryer, linens, towels, gas grille on your private porch. brbrMany returning guests find TREETOPS to be their happy place. (Please note required minimum stays of 28 nights or longer. Due to Key West City transient licensing laws, many historic homes have a 28 night minimum to keep neighborhoods intact.)brbr* OASIS: Simply walk out the double glass doors to an amazing, one of a kind, 70' lagoon style shared pool. Adirondack chairs provided are perfect for reading or having a drink poolside. A Weber gas grille is located on your back porch for your use only. brbrThe spectacular common area backyard is lush and offers both sun and shade. Professional weekly landscapers and pool technicians keep the tropical gardens spotless. brbr* THE POOL: The unique 70' meandering salt water heated or cooled pool. The lagoon pool is shared with five cigar maker style homes. Spotless to swim in and gorgeous to look at, the evening pool and tree lighting is magical. brbrThe owners are very responsive to the needs of their guests and are always happy to answer your questions. Just ask! br________________________________________________________________________________br**TREETOPS is offered exclusively on VRBO. brBuyer Beware: Craigslist does not match owners to properties.

2027 calendar is now available! Old Town historic home Lagoon Pool 3BR ⭐️⭐️⭐️⭐️⭐️

Key West, Florida, United States

Bed

Bath

Sleeps

$354.86

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to The Great Escape, a beautiful 3-bedroom waterfront retreat on Big Coppitt Key, just 10 minutes from downtown Key West! brbr brbrThis ground-level home combines the best of island living with the comfort and convenience you crave. Step outside and soak up the Florida Keys sunshine beside your private heated saltwater pool, where you can unwind with a drink in hand and take in breathtaking sunset views over the water. The outdoor living space is designed for relaxation and fun, complete with lounge seating, a pool house, and plenty of room to enjoy the tropical breeze. Inside, you’ll find a bright and inviting open layout with coastal-inspired décor, a fully equipped kitchen, and comfortable furnishings perfect for families or couples traveling together. Each bedroom offers a serene retreat after a day on the water or exploring nearby Key West. brbr brbrWhether you’re planning to fish, kayak, or simply relax by the pool, The Great Escape offers the perfect home base for your Keys adventure. Experience peaceful waterfront living just minutes from the restaurants, nightlife, and charm of Key West. brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Queen Bed, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sectional Sofa, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 130' of Waterfront (shallow draft, only suitable for kayaks & SUP's) brbr brbr- Saltwater Heated Pool (heated to ~85 degrees Nov-Apr) brbr brbr- Pool House w/ Futon and Smart TV (no cable/satellite TV) brbr brbr- Propane BBQ Grill brbr brbr- Keurig, Drip Coffee Maker, Toaster, Blender brbr brbr- Outdoor Seating brbr brbr- Laundry brbr brbr- Parking for a maximum of 2 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided 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 brbrNo Smoking: 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 brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. 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, three exterior security cameras monitor the property. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

The Great Escape: 3BR Waterfront Retreat, Heated Pool, Stunning Sunsets & Just Minutes to Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$280.67

Summary:brbrCasa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. Take a dip in the heated saltwater plunge pool with waterfall feature and night lighting. The best of Key West is at your fingertips - in Old Town only two blocks from Duval Street! Pet friendly, private parking & perfect for your next extended stay in Key West.brbrbrbrThe Space:brbrCasa Azul is the perfect mix of comfort and stylish. Sleek grey quartz countertops, stainless steel appliances and loads of storage space await you! Get ready to cook with state-of-the-art appliances where you can serve up your goods at the breakfast bar offering up a spot for morning coffee or switch on over to the six-top kitchen table. brbrbrbrBedroom 1: Queen bed brbrFeatures: Full bathroom with walk-in shower and plunge tub, private porch facing Elizabeth street, wardrobe, smart TV & closet.brbrbrbrBedroom 2: Full bed brbrFeatures: Modern full bathroom, smart TV, blackout shades & closet. brbrbrbrUnwind with high-speed wifi, a third full bathroom for guest use & an 80 inch TV for entertaining. Or sit in the sun loungers by the amazing pool to soak in the afternoon rays.brbrbrbrGuest Access:brbrOur self check-in makes the process seamless. brbrbrbrGuests will receive a personalized access code prior to arrival and direct contact to a local guest experience manager for any questions, needs or recommendations during their stay.brbrbrbrThe Neighborhood:brbrLocated right in the middle of Old Town Key West and off of a quiet one-way street in a residential neighborhood. Great bikeable location. brbrbrbrJust two blocks from Duval street where you will be placed on the 600 block.brbrbrbrNearby Restaurants: Mangia Mangia, Onlywood Pizzeria, Miso Happy brbrbrbrWalking distance to famous bars, nightlife, and Key West Landmarks!brbrbrbrGetting Around:brbrParking for 1 vehicle in the driveway and a corresponding space in front of the driveway on the street, both of which are reserved for this property. Any additional street parking is first come first serve and can be difficult to find.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, pedi-cab, moke, scooter, golf cart, Uber, Taxi or by feet. This unit is located in downtown Key West and many attractions are within walking distance. Feel free to ask us for recommendations!brbrbrbrOther Things to Note:brbr- 28-night minimum rental onlybrbr- Private laundry roombrbr- Entire home is Solar powered with back up energybrbr- Pets welcomed

Casa Azul - Private Pool

Key West, Florida, United States

Bed

Bath

Sleeps

$1120.45

If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor space. Slow down, relax and prepare for life the way it should be at Havana Daydream.brbrKey Features: br2 en'suite bedrooms each with porch accessbr4 full bathroomsbrbrLOCATION: This home is located in the gated community of Key Cove, on an exclusive lane of waterfront luxury homes. The perks of this little-known location are many: walking distance to the essentials such a grocery stores and the largest shopping center on the island, while still being tucked away in your own quiet neighborhood. The excitement of downtown Old Town is just a few minutes away by car, moped, or bicycle. This home includes plenty of off-street parking in the private garages, as well as private driveways.brLIVING AREA & KITCHEN: The main entrance to this home is at the top of the stairs leading from the ground level. This 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 8 diners, with additional seating at the kitchen bar. The gourmet kitchen has state-of-the-art appliances and is fully equipped with all of the tools and utensils one could want or need. The sliding glass doors open up to a wide waterfront deck with additional space for a light meal, coffee, a glass of wine, or just taking in the view. brACCOMMODATIONS: This home has two master suites, both of which are located on the top floor. The first master bedroom has a King size bed, a large flat-screen HD TV, and a beautiful two-room en-suite bathroom complete with a glass shower, large Jacuzzi tub and separate room for the facilities. The first master bedroom also has a wall of floor-to-ceiling glass doors opening out to your waterfront balcony, with gorgeous water views. The second master suite is down the opposite hallway, with a King size bed and an en-suite bathroom. The second master suite also has a flat-screen HD TV, large walk-in closet, and a glass sliding door with access to the waterfront balcony. The third bedroom is beside the second master suite, with two twin beds that covert to 1 King upon request, flat screen TV. An additional bathroom is situated in the hall next to the stairs and across from the third bedroom. On the main floor there is a fourth bedroom with two twin beds that also convert to a King bed upon request. This bedroom also has a flat screen TV, and a full bathroom down the hall.brLANAI: Out back is the covered outdoor dining area comfortably seats six and has ample room for entertaining. With visiting heron on the tropical greenery that surround the back yard, your guest will enjoy the natural splendor Havana Daydream and Key West have to offer. Enjoy the brand new, kidney shaped, heated pool. The backyard is complete with a large propane grill. Additional space under the house also offers another covered indoor/outdoor area for playing, additional storage, etc.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.

Spacious Waterfront 4 Bedroom Home

Key West, Florida, United States

Bed

Bath

Sleeps

$623.01

Welcome to Casa Catalina – Your Key West Oasis!brbrStep into the enchanting world of Key West with a stay at the newly renovated Casa Catalina, a stunning historic Conch home that seamlessly blends timeless island charm with modern luxury. Nestled just half a block from Duval Street, this tropical retreat offers the perfect balance of tranquility and excitement, placing you mere moments from world-class dining, eclectic galleries, vibrant nightlife, and sun-soaked beaches.brbrA Spacious Retreat with Island ElegancebrbrCasa Catalina is larger than the typical cigar maker’s cottage, boasting an airy, open-concept design that invites relaxation from the moment you arrive. The living, dining, and kitchen areas flow effortlessly together, creating the perfect space for gathering with loved ones. High-end finishes, coastal-inspired decor, and abundant natural light set the tone for an unforgettable getaway.brbrNewly Designed Primary Suite – Your Private SanctuarybrbrUpstairs, discover a luxurious primary suite, a serene haven complete with a king-size bed, cozy sitting area, chest of drawers, spacious closet, and an en-suite bath. This thoughtfully designed retreat ensures ultimate comfort, offering a peaceful escape after a day of island adventures.brbrUnwind in the Ultimate Outdoor ParadisebrbrStep outside to a tropical backyard oasis, where a heated pool beckons for a refreshing dip, day or night. Whether you’re sipping cocktails at the outdoor bar, catching a game on the poolside TV, or dining al fresco beneath the swaying palms, this outdoor space is designed for endless relaxation and entertainment. Fire up the gas grill, rinse off under the outdoor shower, and soak up the perpetual sunshine of Key West.brbrPrime Location – Walk to Everything!brbrFrom Casa Catalina, you’re just a short stroll away from iconic Key West landmarks, including the Southernmost Point, Ernest Hemingway House, and pristine beaches. Indulge in the city’s best restaurants, boutique shops, and lively bars, all within easy reach. No car needed – simply step outside and embrace the island lifestyle!brbrAccommodations & AmenitiesbrbrSleeps 6 guests comfortablybrbrPrimary Suite (upstairs): King bed, sitting area, en-suite bathbrbrGuest Bedroom (downstairs): Queen bed, full bathbrbrAdditional Sleeping: Sofa converts to a queen bedbrbrFully equipped kitchen for culinary adventuresbrbrFree WiFi & cable TV with smart TVs throughoutbrbrCentral AC & ceiling fans for year-round comfortbrbrWasher & dryer for added conveniencebrbrAll linens provided, including plush beach towelsbrbrWeekly pool & yard maintenance (optional interim housekeeping available)brbrYour Key West Escape Awaits!brbrCasa Catalina is more than just a vacation rental—it’s a tropical sanctuary where memories are made. Pack light—just bring your shorts, swimsuits, and flip-flops—and immerse yourself in the laid-back luxury of island life.brbrBook your stay today and experience the magic of Key West at Casa Catalina!brbr(Owners are licensed Florida real estate brokers.)

Discover the lure of Casa Catalina, a blend of Key West charm and modern comfort

Key West, Florida, United States

Bed

Bath

Sleeps

$453.29

WONDERFUL WATERFRONT HOME ON GORGEOUS LOT...brYou have discovered a prime canal sanctuary second to none in the peaceful enclave of New Town. This fully renovated beauty offers a warm embrace with its welcoming open concept layout and airy cathedral ceilings, replete with a myriad of gathering spaces - indoors and out - for you and your vacationing crew! br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS AND AMENITIES...brYour southernmost splendor begins as you enter this enchanting abode, spirits lifted as the Sonos sound system wafts through the home and pool area, instantly lulling you into island repose. The magnificent chef's kitchen inspires many hours in the happy pursuit of making memories as you entertain and craft epicurean works of deliciousness for an evening of consumption and conversation. The kitchen and ample dining table overlook a plush and expansive great room, complete with surrounding French doors leading to your outdoor retreat. Need to connect with the real world Not a problem as you have a full private office when duty calls. Enjoy a washer and dryer area adjacent to the kitchen for your ultimate convenience. Enjoy live streaming for binge-watching all of your favorite shows!brbrSLEEPING ARRANGEMENTS...brRelish in a perfect night of sleep in one of the 3 large bedrooms designed for ultimate comfort. The first guest room offers twin beds (can convert to a king upon request) and the second features a king bed. A full shower bathroom resides between the two guest rooms and there is also an additional full shower bathroom adjacent to the washer/dryer area off of the kitchen. The primary bedroom comes with a king bed and a large en suite shower bathroom. All of the bedrooms have private doors leading out to the backyard. A queen sofa sleeper resides in the living room. brbrOUTDOOR LIVING...brYour outdoor living oasis is an exquisite tropical dream come true. Enjoy multiple seating and lounging options, overlooking your large heated salt generated pool and waterfall (spa is not available for use). Tie the boat up (with 40 feet of sea wall available) from your fishing adventure and sit at your beautiful tiki bar with an outdoor kitchen that comes with an ice machine and a BBQ station.brbrPARKING...brThis home has plenty of off street parking for your vehicles. brbrPETS...brThis is not a pet friendly home.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)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!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.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). brbrCOME STAY A WHILE...

RISE AND SHINE ~ Canal Front 3 BR/3Ba Home w/ Heated Pool!

Key West, Florida, United States

Bed

Bath

8

Sleeps

$5626.59

Imagine escaping to a luxurious beachfront estate in the magnificent Florida Keys where you and your family, friends or colleagues can relax on a 120-foot private white sand beach or take a refreshing dip in a custom-built heated infinity pool with hot tub overlooking the Atlantic. Cassie’s Paradise, a four bedroom, four bath vacation retreat offers these experiences and so much more. You and your guests can go kayaking, paddle boarding or snorkeling right from the property’s private beach. The nature lovers in your group can walk to nearby nature trails and see wild Key deer and exotic birds in their natural habitat. And that’s just the beginning.brbrCassie’s Paradise offers all the amenities you would expect from a vacation retreat of this caliber: water views from every room, a well-appointed chef’s kitchen, a poolside wet bar and ice maker, a firepit, BBQ grill and beach essentials, including towels, an umbrella, beach blanket and snorkeling gear. Each of the four bedrooms has a king bed, and the home also has two queen pullout beds. For convenience, there are washers and dryers on the first and second floors, and for your peace of mind, the property is equipped with a security system. There’s even a mosquito control system that covers the entire grounds. And for those times when you still need to get some work done, there’s a private den and office where you can take care of business.brbrSomething else that makes this island vacation retreat truly unique is that it offers the best of both worlds: total seclusion and privacy when you want it, while the shopping, dining, bars and lively nightlife of Key West are just minutes away whenever you’re ready to experience them.brbrWith some advance notice, you can even arrange for the services of a personal concierge who will do everything in their power to make your stay as extraordinary as it can be. They can arrange for delivery of food and liquor, the services of a private, in-house chef or any catering or events needs you may have. They will also efficiently handle all types of reservations, whether you need transfers to and from the airport, a private shuttle to Key West, a spa, hair or nail appointment; laundry services or bookings for activities and excursions, including boat charters and scuba and snorkeling trips. How about having a couple of jet skis delivered right to the property’s private beach for your enjoyment They can do that, too. And when it’s time to dine, your concierge can get you into some of the area’s top restaurants, even those that others have trouble getting into. They will also be happy to use their connections to assist with your air travel needs.brMUST BE AT LEAST 25 YEARS OF AGE TO BOOK THIS HOUSEbrbrQuiet Hours 10:00PM-8:00AMbr brAll doors and windows must remain closed at all times. Keeping doors and windows open will over work the AC and not cool the house. Also many bugs can get inside.

Beach Front - Cassie`s Paradise Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$378.03

Welcome to our Key West retreat — a home we cherish and live in part of the year, now open for guests who appreciate comfort, character, and a lived-in sense of ease that you won’t find in a typical vacation rental.brbrLocated just one block from the iconic Green Parrot Bar and two blocks from Duval Street, you’ll be surrounded by the best of Bahama Village — from Blue Heaven, Hemingway House, and Willie T’s to endless galleries, cafes, and music. Yet you’d never guess how close you are while sitting on the quiet, one-block dead-end lane where the home rests. Fort Zachary Taylor Beach and State Park are just a quick bike ride away.brbrInside, you’ll find two full bedrooms and two full bathrooms, including a primary ensuite, each with generous storage, dressers, and hangers to make settling in easy. The kitchen is truly the heart of the home — fully stocked and thoughtfully arranged for everything from margarita making to a full dinner at home, featuring custom tilework, unique countertops, and modern appliances.brbrStart your day with coffee on the covered front porch, and end it in the backyard under the stars — complete with a large swim spa that comfortably fits eight adults, ideal for relaxing or socializing. (Note: The canopy over the deck has been removed, but the surrounding trees provide plenty of natural shade.)brbrRecent updates (2024–2025) include new West Elm living room furniture (sofa, chairs, coffee table), brand new Tempur-Pedic and Purple mattresses, newly upgraded AC units, and an abundance of fresh linens, towels, and kitchen essentials and extras — all part of keeping this space as comfortable for you as it is for us.brbrThis isn’t a typical vacation rental — it’s a home, lovingly maintained and designed for those who want to experience Key West the way locals do: relaxed, refined, and perfectly situated in the heart of Old Town.

Quiet Lane in the Heart of Old Town, Sleeps 4, Dog Friendly

Key West, Florida, United States

Bed

Bath