Key West Rentals
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VRBO
Close enough to Bike Ride to Mallory Square,far away to sleep during FantasyFest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and marina has multiple amenities including two pools, hot tubs, open air restaurant and bar, mar ...
Click For PricingVRBO
- From $274 per night (USD)
Expedia
The Trinidad 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 $274 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $300 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Charming dog-friendly home surrounded by palm trees Close to attractions
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Barefoot Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $209 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Airy, dog-friendly condo with pool, AC, high-speed WiFi, balcony, & hot tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Butterfly Nest 107 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $365 per night (USD)VRBO
- From $340 per night (USD)
Expedia
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $340 per night (USD)Expedia
- From $505 per night (USD)
VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $505 per night (USD)VRBO
- From $649 per night (USD)
Expedia
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a month i ...
From $649 per night (USD)Expedia
- From $921 per night (USD)
VRBO
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $921 per night (USD)VRBO
- From $276 per night (USD)
Expedia
The Barbados by Brightwild | Balcony & Pool View!
- 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 $276 per night (USD)Expedia
- From $199 per night (USD)
VRBO
**FAIRWAY TO HEAVEN @ THE GOLF CLUB** Lavish Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ‘There’s a fe ...
From $199 per night (USD)VRBO
- From $508 per night (USD)
Expedia
Atocha Cottage by Brightwild | Amazing Find!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport district of ...
From $508 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $494 per night (USD)VRBO
- From $150 per night (USD)
Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths. Available May 1st for a 6 month rental 2022. Elegant soph ...
From $150 per night (USD)Expedia
- From $125 per night (USD)
VRBO
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $125 per night (USD)VRBO
- From $2206 per night (USD)
Expedia
Contra House by Brightwild | Luxury Home w\/Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $2206 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $418 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $300 per night (USD)Expedia
- From $336 per night (USD)
VRBO
The Andros by Brightwild | 4th Floor Sunset View
- 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 $336 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Happy’s Houseboat Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $500 per night (USD)Expedia
- From $235 per night (USD)
VRBO
Private Paradise with Heated Waterfall Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $235 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Bohemian Breeze @ Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $303 per night (USD)Expedia
- From $1429 per night (USD)
VRBO
FIN & TONIC Waterfront Condo at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1429 per night (USD)VRBO
- From $114 per night (USD)
Expedia
Centrally located cottage apartment with patio - walk to beach & dining
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $114 per night (USD)Expedia
- From $126 per night (USD)
VRBO
Cozy condo with free WiFi & fantastic location in central Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $126 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $174 per night (USD)Expedia
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Expedia
**LADY EMMA IN THE TRUMAN ANNEX, KEY WEST**
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
DISCOUNTED RATES FOR SPRING/SUMMER!!!Welcome to Lady Emma which is located in the best location in Old Town, the world f ...
Click For PricingExpedia
- From $213 per night (USD)
VRBO
A+ Location in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $213 per night (USD)VRBO
- From $821 per night (USD)
VRBO
AFTERNOON DELIGHT at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $821 per night (USD)VRBO
- From $2564 per night (USD)
Expedia
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
- Bedrooms:
- 10
- Bathrooms:
- 8
- Sleeps:
- 20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2564 per night (USD)Expedia
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Expedia
Luxury Retreat at the Truman Annex near Duval & Beach with Pool, Patio, Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Admirals Gold Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
Click For PricingExpedia
- From $177 per night (USD)
VRBO
Julia's Secret
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $177 per night (USD)VRBO
- From $204 per night (USD)
VRBO
**BIRD of PARADISE** Elegant Home & Pool + 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! Like witnessi ...
From $204 per night (USD)VRBO
- From $1154 per night (USD)
Expedia
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1154 per night (USD)Expedia
- From $1890 per night (USD)
VRBO
Bananas Foster by Brightwild | Epic Guesthouse!
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $1890 per night (USD)VRBO
- From $475 per night (USD)
Expedia
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $475 per night (USD)Expedia
- From $186 per night (USD)
VRBO
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $186 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $240 per night (USD)Expedia
- From $921 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
- 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 $921 per night (USD)VRBO
- From $296 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $296 per night (USD)VRBO
- From $571 per night (USD)
VRBO
2x Standard Two Queen Beds at The Gates Hotel Key West, Swimming 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 $571 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
- 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 $292 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
- 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 $299 per night (USD)VRBO
- From $150 per night (USD)
Expedia
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & 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! This freshly ...
From $150 per night (USD)Expedia
- From $762 per night (USD)
VRBO
Poolside Paradise by Brightwild | Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This 3 bed 2 bath home with a private amazing pool is located right off the quieter end of Duval St. The home c ...
From $762 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Poolside Retreat by Brightwild | Cottage w\/ Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $290 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Updated home with private pool, patio, & grill in enclosed tropical backyard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $228 per night (USD)VRBO
- From $1161 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1161 per night (USD)VRBO
- From $203 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $203 per night (USD)VRBO
- From $520 per night (USD)
Expedia
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. 3 bedro ...
From $520 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Hip Studio in Old Town - Walk to the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $214 per night (USD)VRBO
- From $250 per night (USD)
Expedia
'LA DOLCE VITA' OLD TOWN, STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Historic ...
From $250 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $365 per night (USD)VRBO
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Expedia
Galleon Resort available. 2\/19\/21-2\/26\/21
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
Click For PricingExpedia
- From $254 per night (USD)
VRBO
**BANYAN ROSE @ BEACHSIDE** Modern Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Nestled under ...
From $254 per night (USD)VRBO
- Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For PricingExpedia
- From $826 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $826 per night (USD)VRBO
- Click For Pricing
Expedia
3 blocks from waterfront and 1 block off Duval in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For PricingExpedia
- From $395 per night (USD)
VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $395 per night (USD)VRBO
- From $503 per night (USD)
Expedia
Coconut Palm by Brightwild | Island Home w\/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Coconut Palm is the perfect place for your beautiful tropical getaway in Key West. It is located just one block ...
From $503 per night (USD)Expedia
- From $663 per night (USD)
VRBO
Lazy Lane at The Truman Annex - Pool & Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Lazy Lane at the picturesque Shipyard Condominiums is just a few steps away from Fort Zachary Taylor Beach and ...
From $663 per night (USD)VRBO
- From $702 per night (USD)
Expedia
Casa Key West by Brightwild | Pool & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: - Located on the south end of Duval Street steps from the Southernmost Point! - Large open-concept condo with p ...
From $702 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Sea Breeze by Brightwild | Off-Street Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Sea Breeze is the perfect location for your tropical getaway. This two bedroom condo is located in the heart of ...
From $399 per night (USD)VRBO
- From $1856 per night (USD)
Expedia
Coastal Comfort; Waterfront Luxury Home with private pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1856 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Top Floor Ocean Views from every window Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Key West Paradise Found hes been renovated for 2020 an ...
From $489 per night (USD)VRBO
- From $293 per night (USD)
Expedia
Another Day in Paradise! PRIVATE POOL! Blocks from Duval, 2BR\/2BA in Old Town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*** Located in the Old Town neighborhood. This exclusive residential area of Old Town Key West is really an extension of ...
From $293 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Penthouse Level Ocean Views- Live the Dream
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY You feel the excitement the moment you arrive. The war ...
From $499 per night (USD)VRBO
- From $1734 per night (USD)
Expedia
Havana Daydream; Spacious Waterfront 4 Bedroom Home With Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $1734 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Penthouse Level Ocean Views from every room Tropical Excellence
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY Ocean views from every room with floor to ceiling wind ...
From $499 per night (USD)VRBO
- From $869 per night (USD)
Expedia
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
"Banana Breeze" is an upscale escape by the sea, and considered by some to be a hidden gem. Tucked away in your own oasi ...
From $869 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Hemingway Hideaway in the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Perfectly positioned townhouse in Truman Annex At Historic Foundry building. Hemingway Hideaway in Truman Annex is a de ...
From $450 per night (USD)VRBO
- From $251 per night (USD)
Expedia
Beach House with Ocean View-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
If you are looking to stay in accommodations of high standards. This is the one for you! As you enter this large one bed ...
From $251 per night (USD)Expedia
- Click For Pricing
VRBO
Old Town Island House Near a grocery store, beach, bike rental shop, Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two Story Apartment in central Old Town Key West location. Only a 5 min bike ride to Duval. 1 King size bed on 3rd flo ...
Click For PricingVRBO
- Click For Pricing
Expedia
Castaway Cove by Brightwild | Kayaks, Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Just steps from mangrove tunnels and the breathtaking blue waters of the FL Keys, "Castaway Cove" is the perfec ...
Click For PricingExpedia
- From $307 per night (USD)
VRBO
GREEN SPOT at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our comfortable and delightful 2nd floor condo in the Shipyard section of Truman Annex. Unit #258 is a tastef ...
From $307 per night (USD)VRBO
- From $307 per night (USD)
Expedia
ANOTHER THREE HOUR TOUR at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $307 per night (USD)Expedia
- From $284 per night (USD)
VRBO
CONCH RETREAT Truman Annex Condo with 2 decks, Close to Beach, 2 Bikes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the prestigious Truman An ...
From $284 per night (USD)VRBO
- From $345 per night (USD)
Expedia
**MIDTOWN MOSAIC @ MIDTOWN** Modern Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Spanning an e ...
From $345 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Conch House in the Historic District
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a piece of paradise with a beautiful conch home located in the historic district of Key West. 4-bedrooms, 2 ba ...
From $135 per night (USD)VRBO
- From $238 per night (USD)
Expedia
Salt Pond Hideaway | Cute Condo w\/ Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: - Recently updated this spacious, airy rental is the perfect location for your next Key West getaway! - If you ...
From $238 per night (USD)Expedia
- Click For Pricing
VRBO
ISLAND SPA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
Click For PricingVRBO
- Click For Pricing
Expedia
Luxury Galleon Resort & Marina 2 Bed\/2 Bath Marina View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is located in the heart of Old Town Key West and the Marina is one of the most desired harbors in the ...
Click For PricingExpedia
- From $307 per night (USD)
VRBO
BLUE HEAVEN at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $307 per night (USD)VRBO
- From $268 per night (USD)
Expedia
A Bella Capri in Key West by the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $268 per night (USD)Expedia
- From $221 per night (USD)
VRBO
OYSTER'S PEARL at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $221 per night (USD)VRBO
- From $1931 per night (USD)
Expedia
**THE LIME & THE COCONUT @ OLD TOWN** 6BR\/6BA Compound + LAST KEY SERVICES..
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! According to ...
From $1931 per night (USD)Expedia
- From $500 per night (USD)
VRBO
A LATITUDE ADJUSTMENT at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been recently renov ...
From $500 per night (USD)VRBO
- From $396 per night (USD)
Expedia
ANOTHER DAY IN PARADISE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $396 per night (USD)Expedia
- From $829 per night (USD)
VRBO
A SUNSET BREEZE in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $829 per night (USD)VRBO
- From $350 per night (USD)
Expedia
A SUNSET POOLSIDE at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $350 per night (USD)Expedia
- From $379 per night (USD)
VRBO
ARCHIPELAGO ll at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining ...
From $379 per night (USD)VRBO
- From $221 per night (USD)
Expedia
ALHAMBRA at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $221 per night (USD)Expedia
- From $379 per night (USD)
VRBO
SAILOR'S STORY at The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $379 per night (USD)VRBO
- From $350 per night (USD)
Expedia
AQUA OASIS at The Truman Annex in Key West..
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $350 per night (USD)Expedia
- From $372 per night (USD)
VRBO
CONCH ISLAND at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $372 per night (USD)VRBO
- From $537 per night (USD)
Expedia
*Casa-Amelia-Key-West* 1\/2 block off Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your home away from home! Casa Amelia is a charming Conch house in the historic Gato Cigar Village. Wake up ...
From $537 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Spacious, waterfront condo w\/ a full kitchen, shared pool, & furnished balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunset at Harbour Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $435 per night (USD)VRBO
- From $105 per night (USD)
Expedia
The Marguerite, 603 #3 Elizabeth Street, Old Town Key West monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, One Bathroom apartment in Old Key West. It is located upstairs with an outside entrance and has dormer ceil ...
From $105 per night (USD)Expedia
- From $155 per night (USD)
VRBO
Poolside Paradise in Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the best of Key West! Poolside Paradise is located in the Key West Golf Club. Our townhome is located direc ...
From $155 per night (USD)VRBO
- From $561 per night (USD)
Expedia
Commodore's Cove by Brightwild | Private Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Commodore's Cove offers the best of Key West: a prime location and all the amenities of home. Up to 12 can stay ...
From $561 per night (USD)Expedia