Key West Rentals
- From $736 per night (USD)
VRBO
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 $736 per night (USD)VRBO
- From $245 per night (USD)
Expedia
**SUGARPOPPY COTTAGE** Cozy Cottage \/ Private Pool + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Look for the ...
From $245 per night (USD)Expedia
- From $3163 per night (USD)
VRBO
Takeover at the Grand Maloney by Brightwild
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $3163 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Get the gang ...
From $1200 per night (USD)Expedia
- From $153 per night (USD)
VRBO
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 $153 per night (USD)VRBO
- From $563 per night (USD)
Expedia
Hidden Beach - the perfect place to stay in Key West
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Hidden Beach Unit 3 - In Old Town, just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. ...
From $563 per night (USD)Expedia
- From $1546 per night (USD)
VRBO
Key West - Historic & Charming - Main House
- 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 $1546 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Banyan Resort - 2 Blocks to Sunset Celebration
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Banyan Resort is the ultimate destination for a weekend get-a-way or long term accommodations in our well appointed ...
From $375 per night (USD)Expedia
- From $757 per night (USD)
VRBO
ARCHIPELAGO at The Truman Annex in Key West
- Bedrooms:
- 5
- 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 $757 per night (USD)VRBO
- From $586 per night (USD)
Expedia
SUNSET DALITE at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $586 per night (USD)Expedia
- From $586 per night (USD)
VRBO
AQUA BREEZE at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $586 per night (USD)VRBO
- From $473 per night (USD)
Expedia
Hidden Beach Unit 1. The perfect place to stay in Key West for less
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hidden Beach Unit 1 - Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach ...
From $473 per night (USD)Expedia
- From $307 per night (USD)
VRBO
SHADY NOOK at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $307 per night (USD)VRBO
- From $212 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $212 per night (USD)Expedia
- From $307 per night (USD)
VRBO
ROYAL POINCIENA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $307 per night (USD)VRBO
- From $585 per night (USD)
Expedia
THE PLANTATION at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $585 per night (USD)Expedia
- From $821 per night (USD)
VRBO
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 $821 per night (USD)VRBO
- From $429 per night (USD)
Expedia
LIFE IN THE SLOW LANE at the Truman Annex in Key West
- Bedrooms:
- 3
- 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 $429 per night (USD)Expedia
- Click For Pricing
VRBO
SALTWATER ANGLER at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
Click For PricingVRBO
- From $307 per night (USD)
Expedia
Island Breezes at The Truman Annex in Key West@ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $307 per night (USD)Expedia
- From $586 per night (USD)
VRBO
WORLDS END at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $586 per night (USD)VRBO
- From $316 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $316 per night (USD)Expedia
- From $294 per night (USD)
VRBO
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful gated home is located on an oversized corner lot a few blocks from White Street Pier and Higg's Beach wit ...
From $294 per night (USD)VRBO
- From $407 per night (USD)
Expedia
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 $407 per night (USD)Expedia
- From $364 per night (USD)
VRBO
DANCING PALMS at 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. Leave the c ...
From $364 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful views and close to Duval Street festivities and boat docks. Wks 29-30.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
Click For PricingVRBO
- From $473 per night (USD)
VRBO
Oceanfront Hidden Beach Unit 2 - The best place to stay in Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlan ...
From $473 per night (USD)VRBO
- From $586 per night (USD)
Expedia
OCEAN BREEZE at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $586 per night (USD)Expedia
- From $379 per night (USD)
VRBO
SAGO PALM at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $379 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
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 $1500 per night (USD)Expedia
- From $305 per night (USD)
VRBO
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 $305 per night (USD)VRBO
- From $303 per night (USD)
Expedia
The Bolivar, Old Town Key West Monthly vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tuck upstairs in the back of a historic Conch house is a home away from home with private back porch. 1 Block walk from ...
From $303 per night (USD)Expedia
- From $472 per night (USD)
VRBO
~ 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 $472 per night (USD)VRBO
- From $272 per night (USD)
Expedia
The Patricia, 1 BR, 1 BA monthly vacation rental home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of Old Town Key West is a quaint Key West Home that offers a crisp palette of blue, lime and white ...
From $272 per night (USD)Expedia
- From $424 per night (USD)
VRBO
Come stay in an amazing house close to everything! Duvall! North Seaport!
- Bedrooms:
- 3
- 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 $424 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We want you to know that your safety and comfort while in Key West is our utmost priority. Cleaning supplies are availab ...
From $375 per night (USD)Expedia
- From $489 per night (USD)
VRBO
CEASAR'S PARADISE - A MODERN LUXURY RETREAT W\/ 4+ Bedrooms\/ 5.5 Baths
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Modern sophistication is the design aesthetic in this newer built home in Old Town Key West with designer touches throug ...
From $489 per night (USD)VRBO
- From $699 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 $699 per night (USD)Expedia
- From $661 per night (USD)
VRBO
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
- 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 $661 per night (USD)VRBO
- From $245 per night (USD)
Expedia
Garden of Roses | Tropical Conch Home, Pvt Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Feel like a Key West local by immersing yourself in the heart of all the action at Garden of Roses! This 3-bed, ...
From $245 per night (USD)Expedia
- From $515 per night (USD)
VRBO
VILLA BELLA - AN EXCEPTIONAL 5\/4 ISLAND HOME-Convenient to Old Town
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
28 Night Minimum Stay Required. This beautiful island retreat is secluded away on a quiet Old Town lane and features 5 l ...
From $515 per night (USD)VRBO
- From $435 per night (USD)
VRBO
TUCKED AWAY OFF DUVAL - A contemporary home w\/ local color at your door step
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 9
Location, location, location! Tucked Away is set on a small lane just one block from Duval Street, 2 blocks to the Hemin ...
From $435 per night (USD)VRBO
- From $358 per night (USD)
VRBO
The Salt Cay by Brightwild | Sunset Views, Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $358 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nice quiet vacation landing a few blocks from the action on Duval Street. This Saturday-Saturday home in Key West has: - ...
From $237 per night (USD)Expedia
- From $369 per night (USD)
VRBO
Best location in town. Walk or ride and cover the whole island.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walk everywhere from this little part of Paradise, you will never need a car. Located in beautiful Old Town, you are vi ...
From $369 per night (USD)VRBO
- From $699 per night (USD)
Expedia
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 $699 per night (USD)Expedia
- From $1299 per night (USD)
VRBO
Sailor's Son: Waterfront 4 Bedroom 4 bath Luxury 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 $1299 per night (USD)VRBO
- From $204 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest
- 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 $204 per night (USD)Expedia
- From $276 per night (USD)
VRBO
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 ...
From $276 per night (USD)VRBO
- From $199 per night (USD)
Expedia
Sea Breeze at 1800 Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New Listing January 2022! Sea Breeze at 1800 Atlantic is a two bedroom / two bathroom fully furnished condo located in ...
From $199 per night (USD)Expedia
- From $377 per night (USD)
VRBO
St. Martin Suite | Beautifully Updated, Pool View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the tropical & relaxing Sunrise Suites Resort, located on the quiet side of Key West! - Just 1 mil ...
From $377 per night (USD)VRBO
- From $335 per night (USD)
Expedia
The Exuma Cay by Brightwild | Pool View & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $335 per night (USD)Expedia
- From $599 per night (USD)
VRBO
1 BLOCK OFF DUVAL! PRIVATE POOL AND HOT TUB
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy one of Old Town's wonderful historic homes with private pool and hot tub. Casa Rosa one of only seventy five remai ...
From $599 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Sunny, Dog-Friendly Historical Home w\/ Private Hot Tub, Central AC, WiFi, & W\/D
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Eloise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $200 per night (USD)Expedia
- From $450 per night (USD)
VRBO
BEACHFRONT-Coconut Beach Resort, 7 nights only, May 11-18, on Atlantic, beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Private tropical Paradise on the Atlantic Ocean in Key West, Florida. This condo unit is a 1 bedroom, with 2 full bathro ...
From $450 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
- Bedrooms:
- 3
- 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 $300 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2\/2 baths.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room . We sleep 5 g ...
From $360 per night (USD)VRBO
- From $775 per night (USD)
VRBO
Get Ready for Your Florida Adventure! Nightlife, Bike Rentals, 3 Pools, Spa!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $775 per night (USD)VRBO
- From $2523 per night (USD)
VRBO
Step Out onto Legendary Duval Street! 2 Modern Units, Beach Access, Restaurant!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $2523 per night (USD)VRBO
- From $573 per night (USD)
VRBO
Your Exciting Florida Vacay Starts Here! Nightlife, Island View, Restaurant!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $573 per night (USD)VRBO
- From $713 per night (USD)
VRBO
Beachside Dream! Steps to Sand, Pool, Beach Bar, Nightlife! Near Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $713 per night (USD)VRBO
- From $618 per night (USD)
VRBO
La Mer Dewey Island View Accommodation at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $618 per night (USD)VRBO
- From $521 per night (USD)
VRBO
Tropical Key West Getaway! Enjoy Island View from your Room, Swimming Pools!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $521 per night (USD)VRBO
- From $1197 per night (USD)
VRBO
2 x Partial Ocean View Balcony 2 Queen Beds Rooms at Southernmost Beach Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1197 per night (USD)VRBO
- From $601 per night (USD)
VRBO
Your Key West Adventure Awaits! Ocean View, Pool, Outdoor Dining, Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $601 per night (USD)VRBO
- From $781 per night (USD)
VRBO
Steps From The Sand! Ocean Views, 3 Pools, Onsite Dining, Bike Rental, Nightlife
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $781 per night (USD)VRBO
- From $582 per night (USD)
VRBO
Steps from the Sand! Ocean Views, 3 Pools, Nightlife, Near Southernmost Point!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $582 per night (USD)VRBO
- From $538 per night (USD)
VRBO
Authentic Florida Experience! Nightlife, Spa, Oceanfront Pool, Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $538 per night (USD)VRBO
- From $1425 per night (USD)
VRBO
Your Florida Adventure Awaits! 2 Contemporary Units, Bike Rental, Onsite Dining!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1425 per night (USD)VRBO
- From $707 per night (USD)
VRBO
Partial Ocean View Balcony Two Queen Room at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $707 per night (USD)VRBO
- From $3785 per night (USD)
VRBO
Outdoor Pool with Ocean View! 3 Modern Units, Near Jackson Square & Sunset Pier!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $3785 per night (USD)VRBO
- From $659 per night (USD)
VRBO
Ocean View King Room at Southernmost Beach Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $659 per night (USD)VRBO
- From $613 per night (USD)
VRBO
Experience Florida Like Never Before! Oceanfront Pool, Nightlife, Beach Bar!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $613 per night (USD)VRBO
- From $2130 per night (USD)
VRBO
3 Partial Ocean View Rooms w\/Balcony & 2 Queen Beds at Southernmost Beach Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $2130 per night (USD)VRBO
- From $1796 per night (USD)
VRBO
Get Ready for Your Florida Adventure! 3 Modish Units, Bike Rentals, Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $1796 per night (USD)VRBO
- From $940 per night (USD)
VRBO
Amazing Stay w\/ Fantastic View in Key West! 3 Convenient Rooms, Outdoor Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $940 per night (USD)VRBO
- From $334 per night (USD)
VRBO
Your Next Getaway is Here! Deluxe Fantastic View Two Queen Beds, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $334 per night (USD)VRBO
- Click For Pricing
Expedia
Indoor \/ Outdoor Living in Old Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
Click For PricingExpedia
- From $538 per night (USD)
VRBO
Great for Getaways on the Lush Island of Key West! 3 Poos, Nightlife, Beach Bar!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step out onto legendary Duval Street, the epicenter of Key West dining and nightlife. Sip refreshing cocktails by one of ...
From $538 per night (USD)VRBO
- From $1248 per night (USD)
VRBO
4x Pool View Two Queen Beds at The Gates Hotel Key West, Onsite Swimming Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1248 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Standard Two Queen Beds at The Gates Hotel Key West, Onsite Pool, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $307 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Tropical Dream! Pool, Restaurant, Bar, Gym, Bike Rental, Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $307 per night (USD)VRBO
- From $1225 per night (USD)
VRBO
Key West Dream! 4 Serene Units, Pool, Restaurant, Parking, Gym!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1225 per night (USD)VRBO
- From $1315 per night (USD)
VRBO
Escape to the Keys! 4 Amazing Units, Pool, Restaurant, On-Site Bar, Parking!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1315 per night (USD)VRBO
- From $580 per night (USD)
VRBO
Key West Dream! 2 Awesome Units, Pool, Restaurant, Bar, Bike Rentals, Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $580 per night (USD)VRBO
- From $628 per night (USD)
VRBO
2x Pool View Two Queen Beds Rooms at The Gates Hotel Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $628 per night (USD)VRBO
- From $1161 per night (USD)
VRBO
4 Standard 2 Queens Rooms at The Gates Hotel Key West
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $1161 per night (USD)VRBO
- From $342 per night (USD)
VRBO
Welcome to a Sun-Soaked Paradise! Discover the History and Soul of Key West!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $342 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Key West Getaway! Pool, Restaurant, Bar, Gym, Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $291 per night (USD)VRBO
- From $919 per night (USD)
VRBO
3 Standard 2 Queens Rooms at The Gates Hotel Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $919 per night (USD)VRBO
- From $664 per night (USD)
VRBO
Tropical Experience! 2 Gorgeous Units, Restaurant, Bar, Pool, Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $664 per night (USD)VRBO
- From $910 per night (USD)
Expedia
**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
- 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 $910 per night (USD)Expedia
- From $186 per night (USD)
VRBO
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR\/2BA Cottage + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You have many ...
From $186 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Dream Vacation! Near Famous Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $399 per night (USD)VRBO
- From $937 per night (USD)
VRBO
3 Pool View 2 Queens Rooms at The Gates Hotel Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $937 per night (USD)VRBO
- From $1518 per night (USD)
VRBO
Perfect Key West Staycation Perfect For Your Family! Four Relaxing Rooms, Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Located in the entertainment district in Key West and close to the airport, this property offers great amenities to help ...
From $1518 per night (USD)VRBO
- Click For Pricing
VRBO
Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart of Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Casa Sol, your charming retreat in the heart of Old Town Key West! This delightful Conch House offers you the ...
Click For PricingVRBO
- From $425 per night (USD)
Expedia
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa\/Shared Pool, Near Duval St & Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your perfect oasis at the "Tropical Old Town Bungalow," a charming 2nd-floor unit nestled between the vibrant a ...
From $425 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Classic Key West living w\/ a full kitchen, balcony, & shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $355 per night (USD)VRBO
- From $206 per night (USD)
Expedia
~Reel Paradise~Beautiful private townhouse in a small gated community.
- Bedrooms:
- 3
- 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 $206 per night (USD)Expedia