Key West Rentals
From $602 per night (USD)VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $602 per night (USD)VRBO
From $402 per night (USD)Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $402 per night (USD)Expedia
From $592 per night (USD)VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $592 per night (USD)VRBO
From $299 per night (USD)Expedia
Tailgate Key at the Key West Golf Club in key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $299 per night (USD)Expedia
From $1067 per night (USD)VRBO
Sweet's Spot at The Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $1067 per night (USD)VRBO
From $289 per night (USD)Expedia
Red Room at the Grand Maloney
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $289 per night (USD)Expedia
From $211 per night (USD)VRBO
Best Time at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautif ...
From $211 per night (USD)VRBO
From $425 per night (USD)Expedia
**ISLAND OPULENCE @ MIDTOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! The moment yo ...
From $425 per night (USD)Expedia
From $220 per night (USD)VRBO
Poolside Hangover at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is an amazing second floor two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy yo ...
From $220 per night (USD)VRBO
From $331 per night (USD)Expedia
A Duck on the Green at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $331 per night (USD)Expedia
From $563 per night (USD)VRBO
Southernmost Sanctuary at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $563 per night (USD)VRBO
From $196 per night (USD)Expedia
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 Atlantic Experience comfort and elegance in this beautifully reno ...
From $196 per night (USD)Expedia
From $234 per night (USD)VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $234 per night (USD)VRBO
From $1069 per night (USD)Expedia
Oversized home for the whole family w/private pool & dock
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $1069 per night (USD)Expedia
From $337 per night (USD)VRBO
High Tide at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
If you have high expectations, you are going to enjoy staying at High Tide. You are within walking distance to restaura ...
From $337 per night (USD)VRBO
From $211 per night (USD)Expedia
A Conch Escape at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $211 per night (USD)Expedia
From $211 per night (USD)VRBO
A SUNSET VIEW at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town area. This ...
From $211 per night (USD)VRBO
From $369 per night (USD)Expedia
Gypsy's Palace at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Fabulous waterfront two level condo in the beautiful Historic Mills Place Hospital Building in the Truman Annex awaits! ...
From $369 per night (USD)Expedia
From $339 per night (USD)VRBO
Archipelago l at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $339 per night (USD)VRBO
From $805 per night (USD)Expedia
**THE ADMIRAL'S ESTATE** Grand Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Like many hig ...
From $805 per night (USD)Expedia
From $762 per night (USD)VRBO
Oceanfront 4-Bed 3-Bath home with pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4 Bedroom, 3 Bathroom, Sleeps 8 Luxurious furnishings and spacious interiors centered around the expansive water views p ...
From $762 per night (USD)VRBO
From $442 per night (USD)Expedia
Sky Loft - Steps from Duval Street & Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Du ...
From $442 per night (USD)Expedia
From $2946 per night (USD)VRBO
Takeover at the Grand Maloney
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a boutique hotel located in the heart of downtown Key West. Our signature red brick ...
From $2946 per night (USD)VRBO
From $476 per night (USD)Expedia
Blue Lagoon at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This cheery property located on Southard Street features three bedrooms, one on the first level and two on on the second ...
From $476 per night (USD)Expedia
From $1698 per night (USD)VRBO
**BELLE OF THE BEACH @ CASA EAST** Beach House + Last Key White Glove Service...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1698 per night (USD)VRBO
From $315 per night (USD)Expedia
Sailor's Sanctuary - A Renovated Condo in Old Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated ground floor apartment in Truman Annex. Steps from Duval Street! Enjoy all that the beautiful gated community ...
From $315 per night (USD)Expedia
From $2250 per night (USD)VRBO
Historic Old Town Key West - Main House, 4 beds, 1 Sleeper Sofa, Accommodates 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW The 'Main House' is a two-story, four (4) bedroom, one and a half (1.5) bathroom renovated historic home. The ...
From $2250 per night (USD)VRBO
From $551 per night (USD)Expedia
Archipelago at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This gorgeous townhouse has 4 bedrooms, 4 full Bathrooms, and 2 half bathrooms. It is unique in that it has 2 of everyt ...
From $551 per night (USD)Expedia
From $662 per night (USD)VRBO
Sunset Dalite at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! This gorgeous condo ...
From $662 per night (USD)VRBO
From $492 per night (USD)Expedia
Aqua Breeze at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $492 per night (USD)Expedia
From $211 per night (USD)VRBO
Shady Nook at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This first floor 2 bedroom, 1 bath condo is a blend of Key West charm, modern comfort and unbeatable location! You'll en ...
From $211 per night (USD)VRBO
From $302 per night (USD)Expedia
A Palm Tree Paradise @ the Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise - Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and re ...
From $302 per night (USD)Expedia
From $464 per night (USD)VRBO
Royal Poinciana >>WEEKLY RENTAL! Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WEEKLY RENTAL - This property has the ability to be rented weekly all year long. Nestled in the heart of Old Town Key We ...
From $464 per night (USD)VRBO
From $670 per night (USD)Expedia
A Gulfstream Drift at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Imagine yourself watching the sunset over the ocean from the huge penthouse balcony. This tropical retreat in Paradise h ...
From $670 per night (USD)Expedia
From $286 per night (USD)VRBO
Life in the Slow Lane at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming unit has a whimsical nautical feel with the blue and white décor. There are two master suites, one on t ...
From $286 per night (USD)VRBO
From $415 per night (USD)Expedia
Saltwater Angler at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $415 per night (USD)Expedia
From $536 per night (USD)VRBO
Island Breezes at the Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
WEEKLY RENTAL - This property has the ability to be rented weekly. This charming second floor condominium features two b ...
From $536 per night (USD)VRBO
From $482 per night (USD)Expedia
A Harbour Roost at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $482 per night (USD)Expedia
From $212 per night (USD)VRBO
A Sanctuary Home at the Key West Golf Club in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A Sanctuary Home - Stay on the only 18-hole golf club in the Florida Keys and enjoy the lush tropical foliage and resort ...
From $212 per night (USD)VRBO
From $414 per night (USD)Expedia
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Be Still – Your Private Island Oasis in Key West Nestled on an oversized corner lot just a few blocks from W ...
From $414 per night (USD)Expedia
From $337 per night (USD)VRBO
Ascension at the Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stepping through the white picket gate into this town home located in the gated Truman Annex community, in the heart of ...
From $337 per night (USD)VRBO
From $355 per night (USD)Expedia
DANCING PALMS @ The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay at this bright and airy 2 bedroom, 2 full bath town home in the renowned Truman Annex in Old Town. Convenientl ...
From $355 per night (USD)Expedia
From $482 per night (USD)VRBO
Ocean Breeze at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Gorgeous open water views from this 2-bedroom, 2.5 bath condominium in Harbour Place in the award-winning Truman Annex! ...
From $482 per night (USD)VRBO
From $360 per night (USD)Expedia
Sago Palm at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $360 per night (USD)Expedia
From $1996 per night (USD)VRBO
Features.Key West Suites Hotel has an outdoor pool and fitness center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used ...
From $1996 per night (USD)VRBO
From $401 per night (USD)Expedia
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $401 per night (USD)Expedia
From $649 per night (USD)VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We love this home, and we just know you will too!! A fully renovated conch home with amazing finishes and 3 great bedro ...
From $649 per night (USD)VRBO
From $661 per night (USD)Expedia
Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Boli Townhouse is an extraordinary WEEKLY rental property that you will enjoy with only a short walk to Old Town and the ...
From $661 per night (USD)Expedia
From $747 per night (USD)VRBO
**DARLING OF DUVAL @ OLD TOWN** Cottage + Spa + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Don't miss an ...
From $747 per night (USD)VRBO
From $754 per night (USD)Expedia
Two Bedroom Two Bath Balcony Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Two Bedroom Balcony Villa is a gracious two story Key West rental decorated in a tropical style with a living room, ...
From $754 per night (USD)Expedia
From $822 per night (USD)VRBO
VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
29 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $822 per night (USD)VRBO
From $680 per night (USD)Expedia
~ SOLARIS PAIR-A-DISE ~ A garden lover’s dream on a quiet Key West lane.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: If you are looking for that tropical island vibe, look no further! Both sections of this casual home are ...
From $680 per night (USD)Expedia
From $760 per night (USD)VRBO
Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have the perfect accommodation for a family vacation or friends getaway in Old Town Key West, Florida. Our Two-Bedroo ...
From $760 per night (USD)VRBO
From $1081 per night (USD)Expedia
Waterfront 4 Bed 4 Bath Home in Key Cove Landings
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1081 per night (USD)Expedia
From $336 per night (USD)VRBO
Golf Villa - Indulge Without Overpaying - 2BD/2Bath - Large Open Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $336 per night (USD)VRBO
Click For PricingExpedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 1
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The unit located on the first floor has three-dimensional ceilings throughout with indirect LED lighting. The kitchen is ...
Click For PricingExpedia
From $328 per night (USD)VRBO
Sea Breeze at 1800 Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Sea Breeze at 1800 Atlantic — Your Luxurious Oceanfront Escape in Key West Discover the ultimate blend of co ...
From $328 per night (USD)VRBO
From $987 per night (USD)Expedia
Casa Rosa: 4BR/4BA house, pool, near Duval
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida. *Saturday-to-Saturday ...
From $987 per night (USD)Expedia
From $492 per night (USD)VRBO
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $492 per night (USD)VRBO
From $289 per night (USD)Expedia
~Reel Paradise~Beautiful private townhouse in a small gated community.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $289 per night (USD)Expedia
From $735 per night (USD)VRBO
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $735 per night (USD)VRBO
From $825 per night (USD)Expedia
**CASA AMARILLA** Old Town Cottage & Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $825 per night (USD)Expedia
From $428 per night (USD)VRBO
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STEPS TO DUVAL STREET! WALK EVERYWHERE--TO ALL RESTAURANTS, SHOPS AND BARS OF OLD TOWN, KEY WEST!! You wont nee ...
From $428 per night (USD)VRBO
From $704 per night (USD)Expedia
Hyatt Windward Pointe 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
From $704 per night (USD)Expedia
From $817 per night (USD)VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $817 per night (USD)VRBO
From $1108 per night (USD)Expedia
The Mesa House - One block from Duval St
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else ...
From $1108 per night (USD)Expedia
Click For PricingVRBO
Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Lo ...
Click For PricingVRBO
From $279 per night (USD)Expedia
Gulf Getaway | Condo w/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2. ...
From $279 per night (USD)Expedia
From $365 per night (USD)VRBO
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $365 per night (USD)VRBO
From $733 per night (USD)Expedia
Cloud Suite on Duval Street with Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of ...
From $733 per night (USD)Expedia
From $259 per night (USD)VRBO
A Peace of Paradise at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This second floor end unit was completely remod ...
From $259 per night (USD)VRBO
From $794 per night (USD)Expedia
**CASA SERENDIPITY @ OLD TOWN** Home & Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $794 per night (USD)Expedia
From $224 per night (USD)VRBO
**SERENITY ON SOUTHARD @ THE ANNEX** Condo + Last Key White Glove Service...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SERENITY ON S ...
From $224 per night (USD)VRBO
From $285 per night (USD)Expedia
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Mango Tree Cottage – Old Town Key West Gem! Location, Location, LOCATION! Welcome to The Mango Tree Cottage, your ...
From $285 per night (USD)Expedia
From $268 per night (USD)VRBO
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Roosters Perch in Truman Annex, Porter Lane! This spacious corner duplex is flooded with natural light and b ...
From $268 per night (USD)VRBO
From $785 per night (USD)Expedia
The Gideon Lowe House - Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance. Sophistication. Perfection. Welcome to the Gideon Lowe House, a historic treasure in the heart of Old Town Ke ...
From $785 per night (USD)Expedia
From $295 per night (USD)VRBO
Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West! Located in the charming Shipyard Condominium ...
From $295 per night (USD)VRBO
From $1082 per night (USD)Expedia
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1082 per night (USD)Expedia
From $222 per night (USD)VRBO
Sept. spec @ 125 night lodg. With 4 night stay 4th night lodg. is FREE!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Close to beach, Full Kitchen and front porch. Very Reasonably Priced with 12% OFF Lodging + extras.WKLY stays ...
From $222 per night (USD)VRBO
From $849 per night (USD)Expedia
Waterfront Home in Key Cove Landings
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $849 per night (USD)Expedia
From $896 per night (USD)VRBO
Waterfront luxury home with private pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $896 per night (USD)VRBO
From $789 per night (USD)Expedia
Luxury Waterfront Home with private pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $789 per night (USD)Expedia
From $917 per night (USD)VRBO
Modern Waterfront Luxury Home with Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $917 per night (USD)VRBO
From $886 per night (USD)Expedia
Conch style home in Oldtown with private pool AND dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $886 per night (USD)Expedia
From $966 per night (USD)VRBO
Luxury Waterfront Home with Private Pool and Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $966 per night (USD)VRBO
From $211 per night (USD)Expedia
Sept [email protected] + With 4 night stay 4th night FREE lodging!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Outdoor patio, Full kitchen and Close to the beach🌴🍹🐠 WKLY SPECIALS @ 12% OFF Wkly & REDUCED RATES This is a ...
From $211 per night (USD)Expedia
From $1426 per night (USD)VRBO
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $1426 per night (USD)VRBO
From $368 per night (USD)Expedia
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Relax and unwind in this spacious 1,200 sq ft waterfront condo in downtown Key West. Perfect for families and ...
From $368 per night (USD)Expedia
From $364 per night (USD)VRBO
Waterfront Condo + Pool Downtown + Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Experience spacious waterfront living in Key West in this bright 2-bed, 2-bath condo overlooking a marina in D ...
From $364 per night (USD)VRBO
From $912 per night (USD)Expedia
Penthouse Waterfront Dock Pool Condo Near Duval St
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Bring the whole crew to this spacious 2,200 sq ft waterfront penthouse in downtown Key West, perfect for famil ...
From $912 per night (USD)Expedia
From $400 per night (USD)VRBO
Waterfront Dock Pool Key West Near Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Relax in this bright 2nd-floor corner waterfront condo in downtown Key West, offering extra natural light and ...
From $400 per night (USD)VRBO
From $391 per night (USD)VRBO
2 Bedroom Townhome on Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $391 per night (USD)VRBO
From $709 per night (USD)VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $709 per night (USD)VRBO
From $389 per night (USD)VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Duval Street, Smathers Beach, & Old Town charm await—Key West escape begins here This listing is for a room within a ho ...
From $389 per night (USD)VRBO
From $527 per night (USD)VRBO
**MODERN MAJESTY @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $527 per night (USD)VRBO
From $558 per night (USD)Expedia
The Elizabeth Suite | 1 bedroom condo, shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Stay in the heart of Old Town at The Elizabeth Suite, a charming one-bedroom retreat in historic Bayview House ...
From $558 per night (USD)Expedia
From $156 per night (USD)VRBO
The Fleming Suite | 1 bedroom condo w/shared pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Settle into Key West for a month or longer at The Fleming Suite, a spacious one-bedroom retreat in historic Ba ...
From $156 per night (USD)VRBO
From $336 per night (USD)VRBO
Starr`s Suite - 2 person K Suite w/Private Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Starr`s Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $336 per night (USD)VRBO
From $453 per night (USD)VRBO
**THE OSPREY'S NEST** Condo & Pool + Last Key White Glove Service...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $453 per night (USD)VRBO
From $366 per night (USD)Expedia
Our Piece of Paradise-
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $366 per night (USD)Expedia