Florida Keys Rentals
- Click For Pricing
VRBO
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
Click For PricingVRBO
- From $494 per night (USD)
Expedia
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Palma, Live the Lavish Keys Life in the ultimate vacation rental in Key Largo! With a stellar reputation ...
From $494 per night (USD)Expedia
- From $990 per night (USD)
VRBO
Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A funky and fun fisherman's private paradise that we call FISH CAMP, this property has everything needed for a large fam ...
From $990 per night (USD)VRBO
- From $576 per night (USD)
Expedia
Casa Papa Del Mar formerly Ocean Extravaganza - Totally Renovated in 2022.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $576 per night (USD)Expedia
- From $467 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $467 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $175 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $156 per night (USD)VRBO
- From $275 per night (USD)
Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $275 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Beautiful 3 bed\/3 bath Canal Home with Ocean Access in Key largo - 60 foot Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful Key Largo 2 story home has 3 bedrooms, 2 bathrooms upstairs with another full bathroom downstairs. This ...
From $300 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $263 per night (USD)Expedia
- From $381 per night (USD)
VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $381 per night (USD)VRBO
- From $447 per night (USD)
Expedia
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 ...
From $447 per night (USD)Expedia
- From $146 per night (USD)
VRBO
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)VRBO
- From $280 per night (USD)
Expedia
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 $280 per night (USD)Expedia
- From $185 per night (USD)
VRBO
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)VRBO
- From $589 per night (USD)
Expedia
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)Expedia
- From $459 per night (USD)
VRBO
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 $459 per night (USD)VRBO
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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 $399 per night (USD)
VRBO
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 $399 per night (USD)VRBO
- From $537 per night (USD)
Expedia
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 $537 per night (USD)Expedia
- From $419 per night (USD)
VRBO
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)VRBO
- From $129 per night (USD)
Expedia
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)Expedia
- From $443 per night (USD)
VRBO
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)VRBO
- From $150 per night (USD)
Expedia
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)Expedia
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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)
Expedia
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)Expedia
- From $147 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 $147 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 $1191 per night (USD)
VRBO
~ 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 $1191 per night (USD)VRBO
- From $269 per night (USD)
Expedia
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)Expedia
- From $198 per night (USD)
VRBO
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)VRBO
- From $368 per night (USD)
Expedia
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 $368 per night (USD)Expedia
- From $364 per night (USD)
VRBO
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)VRBO
- From $166 per night (USD)
Expedia
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)Expedia
- From $198 per night (USD)
VRBO
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 $198 per night (USD)VRBO
- From $175 per night (USD)
Expedia
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)Expedia
- From $169 per night (USD)
VRBO
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 $169 per night (USD)VRBO
- From $226 per night (USD)
Expedia
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)Expedia
- From $273 per night (USD)
VRBO
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 $273 per night (USD)VRBO
- From $476 per night (USD)
Expedia
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)Expedia
- From $187 per night (USD)
VRBO
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)VRBO
- From $184 per night (USD)
Expedia
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)Expedia
- From $247 per night (USD)
VRBO
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)VRBO
- From $201 per night (USD)
Expedia
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)Expedia
- From $247 per night (USD)
VRBO
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)VRBO
- From $226 per night (USD)
Expedia
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)Expedia
- Click For Pricing
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 $269 per night (USD)
Expedia
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 $269 per night (USD)Expedia
- From $188 per night (USD)
VRBO
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)VRBO
- From $583 per night (USD)
Expedia
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)Expedia
- From $184 per night (USD)
VRBO
Tiny house on the water. Pool, beach, 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 $184 per night (USD)VRBO
- Click For Pricing
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 $999 per night (USD)
VRBO
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 $999 per night (USD)VRBO
- From $550 per night (USD)
Expedia
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 $550 per night (USD)Expedia
- From $981 per night (USD)
VRBO
**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 $981 per night (USD)VRBO
- From $309 per night (USD)
Expedia
**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 $309 per night (USD)Expedia
- From $540 per night (USD)
VRBO
**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 $540 per night (USD)VRBO
- From $531 per night (USD)
Expedia
**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 $531 per night (USD)Expedia
- From $927 per night (USD)
VRBO
**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 $927 per night (USD)VRBO
- From $425 per night (USD)
Expedia
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)Expedia
- From $1805 per night (USD)
VRBO
**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 $1805 per night (USD)VRBO
- From $475 per night (USD)
Expedia
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)Expedia
- From $459 per night (USD)
VRBO
**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 $459 per night (USD)VRBO
- From $2073 per night (USD)
Expedia
**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 $2073 per night (USD)Expedia
- From $718 per night (USD)
VRBO
**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 $718 per night (USD)VRBO
- From $1595 per night (USD)
Expedia
**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 $1595 per night (USD)Expedia
- From $379 per night (USD)
VRBO
**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 $379 per night (USD)VRBO
- From $252 per night (USD)
Expedia
**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)Expedia
- From $225 per night (USD)
VRBO
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)VRBO
- From $440 per night (USD)
Expedia
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 $440 per night (USD)Expedia
- From $380 per night (USD)
VRBO
**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 $380 per night (USD)VRBO
- From $250 per night (USD)
Expedia
**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)Expedia
- From $319 per night (USD)
VRBO
**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 $319 per night (USD)VRBO
- From $1570 per night (USD)
Expedia
**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 $1570 per night (USD)Expedia
- From $414 per night (USD)
VRBO
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 $414 per night (USD)VRBO
- From $245 per night (USD)
Expedia
**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 $245 per night (USD)Expedia
- From $399 per night (USD)
VRBO
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 $399 per night (USD)VRBO
- From $257 per night (USD)
Expedia
Flamingo Nook. Renovated, Private Pool, Canal & Cabana Club Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The ultimate Florida Keys getaway! The Flamingo Nook located at Key Colony Beach near Marathon. Privacy is what separate ...
From $257 per night (USD)Expedia
- From $210 per night (USD)
VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + 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! Located on So ...
From $210 per night (USD)VRBO
- From $489 per night (USD)
Expedia
**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo \/ Pools + 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 $489 per night (USD)Expedia
- From $804 per night (USD)
VRBO
**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine a hom ...
From $804 per night (USD)VRBO
- From $1218 per night (USD)
Expedia
**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 $1218 per night (USD)Expedia
- From $452 per night (USD)
VRBO
**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 $452 per night (USD)VRBO
- From $538 per night (USD)
Expedia
**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 $538 per night (USD)Expedia
- From $1803 per night (USD)
VRBO
**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 $1803 per night (USD)VRBO
- From $339 per night (USD)
Expedia
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 $339 per night (USD)Expedia
- From $432 per night (USD)
VRBO
**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 $432 per night (USD)VRBO
- From $526 per night (USD)
Expedia
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 $526 per night (USD)Expedia
- From $408 per night (USD)
VRBO
**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 $408 per night (USD)VRBO
- From $1799 per night (USD)
Expedia
**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 $1799 per night (USD)Expedia
- From $500 per night (USD)
VRBO
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)VRBO
- From $521 per night (USD)
Expedia
**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 $521 per night (USD)Expedia
- From $839 per night (USD)
VRBO
**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 $839 per night (USD)VRBO
- From $745 per night (USD)
Expedia
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)Expedia
- From $509 per night (USD)
VRBO
**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 $509 per night (USD)VRBO
- From $170 per night (USD)
Expedia
**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)Expedia
- From $308 per night (USD)
VRBO
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 $308 per night (USD)VRBO
- From $225 per night (USD)
Expedia
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)Expedia
- From $776 per night (USD)
VRBO
**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 $776 per night (USD)VRBO
- From $407 per night (USD)
Expedia
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 $407 per night (USD)Expedia