Florida Keys Rentals
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VRBO
Key West Beachfront Luxury 2\/2 Condo A212
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
Click For PricingVRBO
- From $146 per night (USD)
Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $146 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride ...
From $275 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its n ...
From $185 per night (USD)Expedia
- From $589 per night (USD)
VRBO
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $589 per night (USD)VRBO
- From $503 per night (USD)
Expedia
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the ...
From $503 per night (USD)Expedia
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Expedia
~ HARRY TRUMAN SUITE ~ Walk to Duval Street from this beautiful property!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
THE PROPERTY: The Harry Truman Suite is on the first floor, in the front of the building. The suites that comprise the T ...
Click For PricingExpedia
- From $440 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a ...
From $440 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $146 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an e ...
From $175 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...
From $550 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...
From $419 per night (USD)Expedia
- From $129 per night (USD)
VRBO
Joan's Caribbean Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $129 per night (USD)VRBO
- From $443 per night (USD)
Expedia
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Azul, where The Salt Life Meets Luxury! This licensed and legal vacation rental has received hundreds of ...
From $443 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen wit ...
From $150 per night (USD)VRBO
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Expedia
Ocean Serenity East Endless Ocean Views expansive balcony by Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you wou ...
Click For PricingExpedia
- From $150 per night (USD)
VRBO
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $150 per night (USD)VRBO
- From $1141 per night (USD)
Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1141 per night (USD)Expedia
- From $269 per night (USD)
VRBO
No Stairs-Private Tropical Beach-steps from condo-Hi-Speed WIFI-It's Loaded!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ask me about Covid-19 my cancellation policy. Our White Sandy Tropical Private is Beautiful and Private! I also own 3 o ...
From $269 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...
From $198 per night (USD)Expedia
- From $362 per night (USD)
VRBO
NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $362 per night (USD)VRBO
- From $364 per night (USD)
Expedia
Duck Key Darling: Remodeled 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the epitome of luxury at Duck Key Darling, a splendid 2-bedroom, 2-bath Townhouse Villa nestled within Hawks ...
From $364 per night (USD)Expedia
- From $166 per night (USD)
VRBO
Couples paradise-king bed\/AC\/kayaks for your use\/fishing\/snorkeling\/diving
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Comforting king size bed with an extra room for storage or office, and perfect outdoor living space make for a great cou ...
From $166 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $200 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $175 per night (USD)VRBO
- From $195 per night (USD)
Expedia
Breezy Half-Duplex with 35 Ft. Dock. - Cabana Club Access with Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Breezy Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $195 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Dog-friendly waterfront home with dock, pool, gas grill, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ninth Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $226 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Gulf Pointe Paradise
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Pointe Paradise is a tranquil townhouse featuring a balcony with sweeping Gulf of Mexico views. Dockage is availabl ...
From $292 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $476 per night (USD)VRBO
- From $187 per night (USD)
Expedia
Waterfront home with 24-foot dock, shared pool, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Lime on Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $187 per night (USD)Expedia
- From $184 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock, Bay Views, WiFi, and Shared Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $184 per night (USD)VRBO
- From $247 per night (USD)
Expedia
Breezy waterfront home with pool, 35-foot dock & cabana club access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Captain's Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $247 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Dog-Friendly Home with 60-Ft. Dock and Access to Cabana Club and Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Downhome Cabin by the Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $201 per night (USD)VRBO
- From $247 per night (USD)
Expedia
Waterfront Home with 35-Foot Dock and Access to Private Beach and Shared Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ninth Street Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $247 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Waterfront home with 35-ft dock & access to Cabana Club pool & beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal-side Charisma Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $226 per night (USD)VRBO
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Expedia
Waterfront Home with 33-Foot Dock, Outdoor Shower, Large Patio, & Ideal Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise on Patricia Lane Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
Click For PricingExpedia
- From $281 per night (USD)
VRBO
Waterfront Duplex with Shared Pool & Beach Access, 35-ft Dock
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 17
Breezy Palms & Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $281 per night (USD)VRBO
- From $188 per night (USD)
Expedia
Cozy Canal-Front House w\/ Free WiFi and Deck - Close to Beaches & State Park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Aweigh Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $188 per night (USD)Expedia
- From $583 per night (USD)
VRBO
Oceanfront Paradise w Dock for your 35' boat and Huge Tiki and Firepit. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with ice maker, 50" TV, refridgerator, fire p ...
From $583 per night (USD)VRBO
- From $179 per night (USD)
Expedia
Waterfront Tiny House w Pool, Beach, and Boat Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Private community with 2 private beach areas, boat ramp, heated swimming pool, beach volleyball, children's area with pl ...
From $179 per night (USD)Expedia
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Expedia
Kokomo 3\/2 home on canal quick boating access Cudjoe Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully remodeled 3 bedroom 2 bath home with 60’ concrete dockage in Cudjoe Key. Home is perfectly appointed with ev ...
Click For PricingExpedia
- From $1099 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a newly remodeled four bedrooms elegant house. The property has its own private beach located in the heart of Su ...
From $1099 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Oceanfront Duplex with Spectacular Views, Beach, & Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Henry Flagler Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $475 per night (USD)VRBO
- From $425 per night (USD)
Expedia
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + 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! This colorful ...
From $425 per night (USD)Expedia
- From $715 per night (USD)
VRBO
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $715 per night (USD)VRBO
- From $982 per night (USD)
Expedia
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + 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! A trip to Key ...
From $982 per night (USD)Expedia
- From $283 per night (USD)
VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This ultimate ...
From $283 per night (USD)VRBO
- From $521 per night (USD)
Expedia
**SMOOTH SAILING @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! Formerly La B ...
From $521 per night (USD)Expedia
- From $529 per night (USD)
VRBO
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $529 per night (USD)VRBO
- From $889 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + 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! Traveling to ...
From $889 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Sombrero Beach Home on Canal with Private Dock and Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful villa was built in 2018, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $425 per night (USD)VRBO
- From $1794 per night (USD)
Expedia
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $1794 per night (USD)Expedia
- From $1948 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1948 per night (USD)VRBO
- From $730 per night (USD)
Expedia
**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $730 per night (USD)Expedia
- From $1250 per night (USD)
VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $1250 per night (USD)VRBO
- From $345 per night (USD)
Expedia
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Finally, a la ...
From $345 per night (USD)Expedia
- From $252 per night (USD)
VRBO
**LA CASITA EN CIMA @ OLD TOWN** Quaint Cottage By Duval + LAST KEY SERVICE...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This quaint l ...
From $252 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Beautiful Modern House in Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $225 per night (USD)Expedia
- From $477 per night (USD)
VRBO
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well ma ...
From $477 per night (USD)VRBO
- From $437 per night (USD)
Expedia
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach 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 $437 per night (USD)Expedia
- From $250 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic 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! Imagine a tra ...
From $250 per night (USD)VRBO
- From $323 per night (USD)
Expedia
**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine your ...
From $323 per night (USD)Expedia
- From $1585 per night (USD)
VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1585 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Our Nautical Home in Key West is available for amazing prices Summer of 2023
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $418 per night (USD)Expedia
- From $242 per night (USD)
VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern 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! Upscale islan ...
From $242 per night (USD)VRBO
- From $405 per night (USD)
Expedia
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the poo ...
From $405 per night (USD)Expedia
- From $1237 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + 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! For the ultim ...
From $1237 per night (USD)VRBO
- From $431 per night (USD)
Expedia
**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + 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! SHANG-RI-LA i ...
From $431 per night (USD)Expedia
- From $524 per night (USD)
VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ 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! ATLANTIC REFL ...
From $524 per night (USD)VRBO
- From $1701 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + 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! Dreaming of a ...
From $1701 per night (USD)Expedia
- From $361 per night (USD)
VRBO
Botanical Island Delight Key West fantastic discounts for Summer & Fall
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...
From $361 per night (USD)VRBO
- From $382 per night (USD)
Expedia
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $382 per night (USD)Expedia
- From $543 per night (USD)
VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $543 per night (USD)VRBO
- From $391 per night (USD)
Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $391 per night (USD)Expedia
- From $1607 per night (USD)
VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1607 per night (USD)VRBO
- From $500 per night (USD)
Expedia
3 bed 2.5 bath at Coral Lagoon Resort with boat slip directly behind villa!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
We are the No. 1 rated resort in Marathon! Enjoy our renovated luxury villa with boat slip right behind the villa! We ...
From $500 per night (USD)Expedia
- From $514 per night (USD)
VRBO
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling wit ...
From $514 per night (USD)VRBO
- From $770 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A stay in Key ...
From $770 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $500 per night (USD)VRBO
- From $310 per night (USD)
Expedia
**BOHEMIAN RHAPSODY @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You might ask ...
From $310 per night (USD)Expedia
- From $569 per night (USD)
VRBO
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BLUE HERON'S ...
From $569 per night (USD)VRBO
- From $167 per night (USD)
Expedia
**SUNSET POINT @ SUNSET MARINA** Condo \/ Pool & Spa + 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! SUNSET POINT ...
From $167 per night (USD)Expedia
- From $815 per night (USD)
VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SEA CAPTAIN'S ...
From $815 per night (USD)VRBO
- From $429 per night (USD)
Expedia
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This colorful ...
From $429 per night (USD)Expedia
- From $454 per night (USD)
VRBO
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...
From $454 per night (USD)VRBO
- From $545 per night (USD)
Expedia
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As Neptune wa ...
From $545 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Best Deals in Duck Key . 2 Bedroom \/2 Bath w\/40' 'Dock, Trailer Storage Incl,
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the v ...
From $313 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Luxury Waterfront Pool Home Canal Front Direct Ocean Access Fisherman's Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come relax in our Marathon Oasis...This calm, comfortable and modern updated home is a 2/2 with a great open room floor ...
From $450 per night (USD)Expedia
- From $745 per night (USD)
VRBO
Find Sanity in the Heart of Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $745 per night (USD)VRBO
- From $523 per night (USD)
Expedia
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + 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 Old Town ...
From $523 per night (USD)Expedia
- From $170 per night (USD)
VRBO
**SUNSET DREAMS @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUNSET DREAMS ...
From $170 per night (USD)VRBO
- From $319 per night (USD)
Expedia
Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...
From $319 per night (USD)Expedia
- From $225 per night (USD)
VRBO
New Listing! Beautiful Canal front , Key Deer and jacuzzi.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $225 per night (USD)VRBO
- From $742 per night (USD)
Expedia
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $742 per night (USD)Expedia
- From $401 per night (USD)
VRBO
High Tide awaits your next visit upgraded condo close to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...
From $401 per night (USD)VRBO
- From $1404 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1404 per night (USD)Expedia
- From $385 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! FOLLOW THE SU ...
From $385 per night (USD)VRBO
- From $1909 per night (USD)
Expedia
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $1909 per night (USD)Expedia
- From $361 per night (USD)
VRBO
Tranquility by Smathers and 10 minute bike downtown Key West value savings
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...
From $361 per night (USD)VRBO
- From $509 per night (USD)
Expedia
Somewhere on the Beach a dream property all amenities included simply amazing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Somewhere on the Beach has amazing views of the Atlantic Ocean and White Street Pier. The property was completely remode ...
From $509 per night (USD)Expedia