Stock Island, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Stock Island, Florida on RentalSaver.com!

Stock Island Rentals

From $556 per night (USD)
VRBO
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tortuga Hammock Townhouse Highlights: Location: Stock Island, within the gated Coral Hammock community, close to Key Wes ...
From $556 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Upscale Townhome w/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid at Key West Golf Club Our calendar is updated in real-time & our nightly rates are accurately display ...
From $219 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $193 per night (USD)
VRBO
From $711 per night (USD)
Expedia
Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $711 per night (USD)
Expedia
From $696 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
Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock 3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to ...
From $696 per night (USD)
VRBO
From $567 per night (USD)
Expedia
**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 $567 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Family home in gated community w/great amenities, shared pool, fitness center
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Hemingway Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $484 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Fairway Villa w/ Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa — a stunning, spacious 3-bedroom, 3-bathroom townhouse nestled on the beautiful Key West Golf C ...
From $247 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $688 per night (USD)
VRBO
From $703 per night (USD)
Expedia
OCEAN MEMORIES CONDO- 2 Bedroom, 2 Bath Oceanfront w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Oceanfront Escape with Breathtaking Views – Steps from the Marina* Wake up each morning to breathtaking sunrises stre ...
From $703 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the oce ...
From $638 per night (USD)
VRBO
From $548 per night (USD)
Expedia
'Oceanside Oasis' Direct Ocean Views & 3 BR'S
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Imagine waking up every morning to the sun rising over the Atlantic Ocean. That's what you will experience with this bea ...
From $548 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Poolside townhouse in Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful 2 bed/2.5 bath townhome in key west golf club. Pool steps away. Gated community. Enjoy everything beautiful Ke ...
From $231 per night (USD)
VRBO
From $288 per night (USD)
Expedia
GOLF VILLA - Monthly Rental - 2BD/2BA -Community Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Golf Villa, your perfect Key West getaway in the highly sought-after Key West Golf Club neighborhood! Immerse ...
From $288 per night (USD)
Expedia
From $760 per night (USD)
VRBO
The Flight Deck - 3 Bedroom / 3 Bathroom with Shared Pool & Fitness Center!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to “The Flight Deck” — Your Tropical Getaway in Key West Location: Coral Hammock Community, Stock Island – Just ...
From $760 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Key West Home on Deep Water Canal with Pool on Key Haven Road, Fisherman's Dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your private oasis in the heart of Key West, at 28 Key Haven Road. This charming 3-bedroom 2 bathroom vacatio ...
From $552 per night (USD)
Expedia
$Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n$
From $1119 per night (USD)
VRBO
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom ...
From $1119 per night (USD)
VRBO
Click For Pricing
Expedia
Key Haven 3bedroom 2bath canal front home w/boat dock, private pool, parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
Click For Pricing
Expedia
From $207 per night (USD)
VRBO
Key West Home on Golf Course w/ Patio & Grill!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Play a round of golf, snorkel the crystal-clear waters, and explore Key West’s bustling downtown when you stay at this l ...
From $207 per night (USD)
VRBO
From $351 per night (USD)
Expedia
An Island Siesta: 2 BR, 2 BA Townhouse in Key West, Sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $351 per night (USD)
Expedia
From $900 per night (USD)
VRBO
3-bedroom townhome in Key West with fitness room, WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Key West at this lovely townhome. With 3 bedrooms including 2 king beds and 2 queen beds, th ...
From $900 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Quiet 2-bedroom plus office townhome on the Key West golf course!
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Just a short walk from the Resort style pool and fitness center, our townhome, situated on the 1st fairway of the Key We ...
From $168 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Antique trawler 2-bedroom boat in phenomenal Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Key West like a local in this adorable 2-bedroom antique trawler 37' yacht located at The Perry Marina. This ...
From $444 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Cozy Modern Casa Azul Houseboat Experience & Scenic Views @ The Perry
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the Casa Azul Houseboat! Experience tranquility on the water at Perry Marina. This stylish floating haven boa ...
From $491 per night (USD)
VRBO
From $370 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $370 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!$
From $361 per night (USD)
VRBO
Escape to \"Oasis on 18th\" w/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...
From $361 per night (USD)
VRBO
From $539 per night (USD)
VRBO
3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel/Marina
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Living room, Dining room and kitchen all enjoy stunning views of the Atlantic Ocean. Master bedroom and Master bath also ...
From $539 per night (USD)
VRBO
From $523 per night (USD)
Expedia
Tropical Key West out of the way
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Three bedroom (all queens sizes beds) and three full bathroom two story home in a gated community within walking distanc ...
From $523 per night (USD)
Expedia
From $468 per night (USD)
VRBO
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
WELCOME BOATING AND GOLFING ENTHUSIASTS.. Located just off Key West at mile marker 5, the gated community of Coral Hammo ...
From $468 per night (USD)
VRBO
From $458 per night (USD)
Expedia
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING.. Located just off Key West at mile marker 5, the picturesque community of ...
From $458 per night (USD)
Expedia
From $375 per night (USD)
VRBO
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
IDEAL LOCATION FOR BOATERS AND GOLFERS... Located just off Key West at mile marker 5, the picturesque community of Coral ...
From $375 per night (USD)
VRBO
From $1567 per night (USD)
Expedia
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Free Spirit is a 75' Hatteras that has been meticulously cared for. She is the ideal location for gatherings of fami ...
From $1567 per night (USD)
Expedia
From $329 per night (USD)
VRBO
The GUAVA DUFF - Beautiful KW home with space to chill & lots of FREE PARKING!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Total renovation completed in 2020! This 4-bedroom contemporary home is waiting for your arrival! The Guava Duff (named ...
From $329 per night (USD)
VRBO
From $820 per night (USD)
Expedia
Clean and Relaxing!! 3 King Suites!! Home with everything you need
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This beautiful home in Key West has been fully updated with new furnishings. It is located in the upscale Coral Hammoc ...
From $820 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Home away from home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the gated community of the Key West Golf Club, enjoy your morning coffee in the enclosed back porch overlooki ...
From $174 per night (USD)
VRBO
From $295 per night (USD)
VRBO
Eddie Griffiths Overnight Charters and Vacation Rentals!!!!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Its a custom built 43 ft sport fish made for overnight trips with all the comforts of home. Sleeps six and is kept in to ...
From $295 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Monthly Availability beginning May 2025
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
To provide our guests with a clean and sanitized home, our cleaning service cleans AND disinfects all high-touch surface ...
From $226 per night (USD)
VRBO
From $530 per night (USD)
Expedia
Ocean views! <br>I didn’t do it too
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. The ...
From $530 per night (USD)
Expedia
From $591 per night (USD)
VRBO
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Nicest Yacht rental in the keys . Stay on this beautiful, 66 foot, four bedroom, four bathroom yacht and experience luxu ...
From $591 per night (USD)
VRBO
From $621 per night (USD)
Expedia
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
'TEE BY THE SEA' vacation rental (we include 7 bikes, FREE PARKING AND WIFI free for our guests!!!) We're less then 1/2 ...
From $621 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Oceanfront Marina Condo With All Luxuries
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your spacious oceanfront balcony will be a front row seat for a panorama of azure blue ocean and sky. There are touches ...
From $539 per night (USD)
VRBO
From $866 per night (USD)
Expedia
Lifetime memories/Private pool/WiFi/Dog OK/Self check-in-out/High Cleanliness!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This elegant home has been constructed to the highest standards and is located within minutes of downtown Key West (vi ...
From $866 per night (USD)
Expedia
From $675 per night (USD)
VRBO
LUXURY WATERFRONT ESTATE SEAWALL DOCKAGE & POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living ...
From $675 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Key West Vacation Home on Canal
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Beautiful 3 bedroom, 2 bath home with den. Canal-front with included boat dockage, private backyard and a large swim sp ...
From $284 per night (USD)
Expedia
From $711 per night (USD)
VRBO
PET FRIENDLY! SUMMER SPECIALS !! 3 Bedroom 3 bathroom home. Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
"Flip Flop Inn" is a beautiful 3 Bedroom 3 Bath home, (each bedroom has its own private full bath), and a Queen size ...
From $711 per night (USD)
VRBO
From $568 per night (USD)
Expedia
3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A slice of paradise just for you. Quietly enjoy a quintessential view of the Atlantic Ocean and mangrove estuary that wi ...
From $568 per night (USD)
Expedia
From $509 per night (USD)
VRBO
Gone Coastal
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful places to stay. Completely renovated 3 bedroom 2.5 bath townhome in Coral ...
From $509 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Tropical Tee-Time: 2BR Townhome in Key West Golf Club with Two Shared Pools, Fitness Center, Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $270 per night (USD)
Expedia
From $245 per night (USD)
VRBO
PAINTED SKY~2 BR/2 Ba Waterfront Condo at Sunset Marina w/ Pool & Boat Slip!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ISLAND MASTERPIECE... In the private gated community of Sunset Marina, this exquisite waterfront condo's view is awash i ...
From $245 per night (USD)
VRBO
From $624 per night (USD)
Expedia
Mermaid's Retreat at Coral Hammock Key West Island living at its best
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Mermaids Retreat Escape to the tropical charm of Mermaids Retreat, where comfort meets convenience in a sere ...
From $624 per night (USD)
Expedia
From $635 per night (USD)
VRBO
**OCEANFRONT OASIS @ KEY HAVEN** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! OCEANFRONT OA ...
From $635 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover the charm of “Old Key West” aboard Vita Felice, a Luxurious Vintage Yacht and a piece of American History. Thi ...
From $381 per night (USD)
Expedia
Click For Pricing
VRBO
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
You and your guests will have exclusive use of this 50 ft yacht all to yourselves. The yacht stays docked, the entire re ...
Click For Pricing
VRBO
From $572 per night (USD)
Expedia
Waterfront Boater's Paradise on deep water canal, boat dock, ocean access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Tropical WATERFRONT getaway. A Boater's Paradise. This charming 4 bedroom (1 King, 3 Queens), 2 bath house is located on ...
From $572 per night (USD)
Expedia
From $1583 per night (USD)
VRBO
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom ...
From $1583 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Sentient Waters: 63' Boat With Full Amenities & Sun Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome aboard Sentient, your own private 63’ boat in Key West! We're thrilled to have you & hope you enjoy every moment ...
From $458 per night (USD)
Expedia
From $256 per night (USD)
VRBO
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable boat is the perfect home base for your trip to Key West. With 2 pleasant bedrooms featuring queen beds an ...
From $256 per night (USD)
VRBO
From $1192 per night (USD)
Expedia
Luxury 2BR Condo • Oceans Edge Resort, Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy breathtaking ocean views from this 2BR/2BA condo at Oceans Edge Resort in Key West. The master suite features a ki ...
From $1192 per night (USD)
Expedia
From $1085 per night (USD)
VRBO
Your Luxurious Key West Escape Awaits – A Boater’s Dream Retreat!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Your Luxurious Key West Escape Awaits – A Boater’s Dream Retreat... Nestled in the exclusive Key Haven neighborhood, ju ...
From $1085 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Funky Chicken Cottage with shared pool, 3 bed 3 bath minutes from Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover this 3-bedroom gem in Key West. This tranquil townhome offers a wonderful escape for guests. With 1 king bed an ...
From $795 per night (USD)
VRBO
From $291 per night (USD)
VRBO
8th Hole Golf Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Luxury Two-Bedroom Condo with Resort-Style Amenities for Rent in Key West Golf Club Community. ...
From $291 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Decorators own Coastal Chic home
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
BRAND NEW, Coastal on Coral is located in the beautiful gated community of Coral Hammock on the quiet end of Key West on ...
From $609 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Private Pool, Outdoor Shower, Pet Friendly, in Golf Course- 5 min to Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Livin' On Key West Time Vacation Rental! This 2-bed 2-bath townhome is located in the prestigious Key West Go ...
From $368 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Triple Crown Villa- Boaters Paradise with Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you're looking for a luxurious and unforgettable waterfront vacation experience, look no further than this stunning v ...
From $642 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Key West - Stock Island
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Two Bedroom and 2 and Half Bath beautiful condo in great private Coral Hammock community, close to Golf Course and short ...
From $349 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Charming 3-bedroom townhome with WiFi, AC in fantastic Key West Golf Course
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Your home away from home in Key West with 3 bedrooms. This adorable townhome features a cozy sofa bed, a comfortable que ...
From $212 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Fun & Energetic 2 Bed 1.5 Bath: Booty Caye @ Key West Golf Club - RealKeyWest
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to your private oasis at Booty Caye, nestled within the exclusive enclave of the Key West Golf Club. This beautif ...
From $181 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Upscale dog-friendly home on golf course with lush back yard & pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tropical Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $304 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Bayfront bungalow with private dock, kayaks, SUPs, tiki hut & pool access
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Sunset Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $523 per night (USD)
VRBO
From $744 per night (USD)
Expedia
Ocean views! <br>No regrets
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. The ...
From $744 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Paradise found
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located on Stock Island this 3 bedroom home is 8 minutes from Duval street. Walking distance to several great restaurant ...
From $547 per night (USD)
VRBO
From $231 per night (USD)
VRBO
2 Bed/2.5 Bath Townhome in KW Golf Club - Backs up to Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly updated townhome on the pool in Key West Golf Club! This newly renovated 2 bedroom/2.5 bathroom townhome is nestl ...
From $231 per night (USD)
VRBO
From $330 per night (USD)
VRBO
**MARINER’S HIDDEN HAVEN @ KEY HAVEN** Waterfront Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Escape the “c ...
From $330 per night (USD)
VRBO
From $188 per night (USD)
Expedia
Coral Breeze by AvantStay | Close to Beach w/ Balcony & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Coral Breeze is a two-bedroom townhome located in t ...
From $188 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Cottage by the Pool by AvantStay | w/ Balcony, BBQ & Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* This cozy 2 bedroom home is nestled in the center o ...
From $187 per night (USD)
VRBO
From $679 per night (USD)
Expedia
Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story townhome located in the private gated community of Coral Hammock o ...
From $679 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Place to Relax by AvantStay | Shared Pool | 3 Miles to Smather's Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Please note that this home is available for 28+ night stays only.* Located in the Sanctuary of the gated community in ...
From $234 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Bogey's Retreat by AvantStay | Golfer's Retreat w/ Shared Pool! |
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Welcome to your home away from home in Key West. Th ...
From $292 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully decorated spacious 3 bedroom, 3 bathroom with off-street parking for 2 vehicles -- a rare commodity in Key W ...
From $671 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coral Garden is a two-bedroom townhome in the quiet gated community of Coral Hammock located on Stock Island. Perfect fo ...
From $453 per night (USD)
Expedia
From $140 per night (USD)
VRBO
Gated Golf Community w/ Pool, Prime Location Mins to Old Town | Long-Term Stays
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
*Please note that this home is available for 28+ day stays only.* Located on the main road meandering through the seclu ...
From $140 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Key West Happy Hideaway! Beautifully Renovated! 2 BDR/1.5 BA, GOLF, POOL, GYM
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key West Happy Hideaway is exactly that! Your perfect little hideaway nestled in the beautiful and lush landscaping of t ...
From $159 per night (USD)
Expedia
$Spacious Fountaine-Pajot S/V \Devine Sailing\ at The Perry Hotel Marina & Resort$
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VRBO
Spacious Fountaine-Pajot S/V \"Devine Sailing\" at The Perry Hotel Marina & Resort
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Set sail for a delightful stay on this 5-bedroom boat in Key West. Each room features a cozy queen bed, ensuring a restf ...
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VRBO
From $3508 per night (USD)
Expedia
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Bedrooms:
5
Bathrooms:
10
Sleeps:
22
This isn't just a house, this is your own private mini resort in Key West, Florida. THERE IS NO OTHER PROPERTY THAT COMP ...
From $3508 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Casa Caribe Beautiful tropical 2 bedroom sleeps 6
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical 2 bedroom, 2.5 bathroom, 2 level Key West townhome to be your home away from home! No detail has been overlooke ...
From $533 per night (USD)
VRBO
From $474 per night (USD)
Expedia
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
NESTLED IN THE HEART OF PARADISE… Stunning views of the ocean and nature surround you in this lovely getaway. Your soul ...
From $474 per night (USD)
Expedia
From $318 per night (USD)
VRBO
HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A SIMPLE GETAWAY… If you are craving a simple yet sensational taste of paradise, look no further. This small but mighty ...
From $318 per night (USD)
VRBO
From $417 per night (USD)
Expedia
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A TRANQUIL GETAWAY FOR 6… Welcome to captivating views of the ocean ideal for unwinding and unpluging from reality. You ...
From $417 per night (USD)
Expedia
From $450 per night (USD)
VRBO
Craig & Cindy Key West Poolside Coral Hammock Royal Palm House 2 bdrm 2.5 bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coral Hammock is a gated communities with 55 luxury resort homes with a lavish Clubhouse and Pool and lushly landscaped ...
From $450 per night (USD)
VRBO
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Expedia
Hyatt Residence Club Windward Pointe Key West 2br/2ba/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
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Expedia
From $767 per night (USD)
VRBO
Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $767 per night (USD)
VRBO
From $1367 per night (USD)
Expedia
Skip the Hotel - Stay on the Water aboard a 46 foot Yacht in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
All aboard this 48 foot motor yacht in Key West. Get ready to live your best life on this yacht, featuring a luxurious p ...
From $1367 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Key West Stay Ideal For Couple Close to Mallory Square | Outdoor Swimming Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $234 per night (USD)
VRBO
From $192 per night (USD)
VRBO
Newly Renovated Hotel w/ Outdoor Pool | Short Drive to Historic Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $192 per night (USD)
VRBO
From $183 per night (USD)
VRBO
Relaxing Double Queen, Fairfield Inn, Breakfast Included, Near Downtown Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore Key West with us! Enjoy proximity to Historic Old Town, known for its rich history, vibrant culture, and stunnin ...
From $183 per night (USD)
VRBO
Click For Pricing
Expedia
Key West Escape
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Luxurious accommodations, recreational amenities include an outdoor pool, a spa tub, and bicycles to rent. This hotel a ...
Click For Pricing
Expedia
From $347 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $347 per night (USD)
VRBO
From $367 per night (USD)
Expedia
**THE OSPREY'S NEST @ SUNRISE SUITES** 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! Want to be in ...
From $367 per night (USD)
Expedia
From $542 per night (USD)
VRBO
Ocean views! <br>Luxury suites
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Your Ocean front vacation house on water awaits you! Experience Key West staying above it's beautiful clear water. The ...
From $542 per night (USD)
VRBO
$Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n$
From $499 per night (USD)
Expedia
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St. \n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2 bedroom (one King and one Queen, plus Queen size pull out couch in the living room), 2 bathroom unit offers all ...
From $499 per night (USD)
Expedia

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