Florida Keys National Marine Sanctuary Rentals
- From $148 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 $148 per night (USD)VRBO
- 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 $136 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 $136 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 $1066 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 $1066 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 $175 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 $175 per night (USD)VRBO
- From $312 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 $312 per night (USD)Expedia
- From $349 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 $349 per night (USD)VRBO
- From $161 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 $161 per night (USD)Expedia
- From $200 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 $200 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 $295 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 $295 per night (USD)VRBO
- From $212 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 $212 per night (USD)Expedia
- From $206 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 $206 per night (USD)VRBO
- From $785 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 $785 per night (USD)Expedia
- From $191 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 $191 per night (USD)VRBO
- From $217 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 $217 per night (USD)Expedia
- From $269 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 $269 per night (USD)VRBO
- From $187 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 $187 per night (USD)Expedia
- From $257 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 $257 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 $223 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 $223 per night (USD)Expedia
- From $198 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 $198 per night (USD)VRBO
- From $496 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 $496 per night (USD)Expedia
- From $244 per night (USD)
VRBO
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 $244 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 $599 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 $599 per night (USD)VRBO
- From $421 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 $421 per night (USD)Expedia
- From $931 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 $931 per night (USD)VRBO
- From $329 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 $329 per night (USD)Expedia
- From $459 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 $459 per night (USD)VRBO
- From $413 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 $413 per night (USD)Expedia
- From $589 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 $589 per night (USD)VRBO
- From $364 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 $364 per night (USD)Expedia
- From $2120 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 $2120 per night (USD)VRBO
- From $882 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 $882 per night (USD)Expedia
- From $384 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 $384 per night (USD)VRBO
- From $1433 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 $1433 per night (USD)Expedia
- From $620 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 $620 per night (USD)VRBO
- From $1200 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 $1200 per night (USD)Expedia
- From $425 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 $425 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 $453 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 $453 per night (USD)VRBO
- From $413 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 $413 per night (USD)Expedia
- From $233 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 $233 per night (USD)VRBO
- From $277 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 $277 per night (USD)Expedia
- From $1099 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 $1099 per night (USD)VRBO
- From $305 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 $305 per night (USD)Expedia
- From $207 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 $207 per night (USD)VRBO
- From $369 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 $369 per night (USD)Expedia
- From $264 per night (USD)
VRBO
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 $264 per night (USD)VRBO
- From $216 per night (USD)
Expedia
**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 $216 per night (USD)Expedia
- From $471 per night (USD)
VRBO
**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 $471 per night (USD)VRBO
- From $675 per night (USD)
Expedia
**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 $675 per night (USD)Expedia
- From $912 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 $912 per night (USD)VRBO
- From $356 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 $356 per night (USD)Expedia
- From $528 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 $528 per night (USD)VRBO
- From $1647 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 $1647 per night (USD)Expedia
- From $369 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 $369 per night (USD)VRBO
- From $383 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 $383 per night (USD)Expedia
- From $442 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 $442 per night (USD)VRBO
- From $375 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 $375 per night (USD)Expedia
- From $1350 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 $1350 per night (USD)VRBO
- From $425 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 $425 per night (USD)Expedia
- From $355 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 $355 per night (USD)VRBO
- From $744 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 $744 per night (USD)Expedia
- From $747 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 $747 per night (USD)VRBO
- From $465 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 $465 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 $279 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 $279 per night (USD)Expedia
- From $250 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 $250 per night (USD)VRBO
- From $677 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 $677 per night (USD)Expedia
- From $417 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 $417 per night (USD)VRBO
- From $1267 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 $1267 per night (USD)Expedia
- From $344 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 $344 per night (USD)VRBO
- From $1715 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 $1715 per night (USD)Expedia
- From $304 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 $304 per night (USD)VRBO
- From $469 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 $469 per night (USD)Expedia
- From $699 per night (USD)
VRBO
4 Bed 3 Bath Duck Key Sanctuary Villa W\/ Private Pool & 35 Foot Dock - Sleeps 10
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
We offer a unique Sanctuary Villa located on the island of Duck Key. This 4 bedroom 3 bath villa sleeps 10 people comfor ...
From $699 per night (USD)VRBO
- From $510 per night (USD)
Expedia
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For many, the ...
From $510 per night (USD)Expedia
- From $1318 per night (USD)
VRBO
**DIAMOND GIRL @ THE ANNEX** Elegant 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! Seals & Croft ...
From $1318 per night (USD)VRBO
- From $693 per night (USD)
Expedia
**THE SMILING IBIS @ 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 $693 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Waterfront luxury Villa (30) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $354 per night (USD)VRBO
- From $363 per night (USD)
Expedia
**NATURES EDGE @ 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! NATURE'S EDGE ...
From $363 per night (USD)Expedia
- From $419 per night (USD)
VRBO
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious 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! OCTOPUS'S GAR ...
From $419 per night (USD)VRBO
- From $492 per night (USD)
Expedia
Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic 4th floor condominiums unit C439. Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, tw ...
From $492 per night (USD)Expedia
- From $549 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 $549 per night (USD)VRBO
- From $528 per night (USD)
Expedia
**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 $528 per night (USD)Expedia
- From $167 per night (USD)
VRBO
**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)VRBO
- From $815 per night (USD)
Expedia
**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)Expedia
- From $406 per night (USD)
VRBO
**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 $406 per night (USD)VRBO
- From $445 per night (USD)
Expedia
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 $445 per night (USD)Expedia
- From $566 per night (USD)
VRBO
**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 $566 per night (USD)VRBO
- From $325 per night (USD)
Expedia
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 $325 per night (USD)Expedia
- From $450 per night (USD)
VRBO
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)VRBO
- From $151 per night (USD)
Expedia
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + 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! SUNDRENCHED R ...
From $151 per night (USD)Expedia
- From $345 per night (USD)
VRBO
**SOUTHERNMOST SOLACE @ OLD TOWN** Conch Cottage 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! At the Southe ...
From $345 per night (USD)VRBO
- From $1127 per night (USD)
Expedia
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $1127 per night (USD)Expedia