
Stock Island Rentals

- From $445 per night (USD)
VRBO
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tortuga Hammock is located on Stock Island in the Coral Hammock private gated community. This 2 bedroom 2.5 bathroom t ...
From $445 per night (USD)VRBO
- From $231 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 $231 per night (USD)Expedia
- From $485 per night (USD)
VRBO
Spotless Fully Renovated Family Home. Free parking WiFi Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in ...
From $485 per night (USD)VRBO
- From $192 per night (USD)
Expedia
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 $192 per night (USD)Expedia
- From $571 per night (USD)
VRBO
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 $571 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Hidden Paradise-2bed 2bath condo w/ ocean views, dock space, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $215 per night (USD)Expedia
- From $493 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 $493 per night (USD)VRBO
- From $391 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 $391 per night (USD)Expedia
- From $452 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 $452 per night (USD)VRBO
- From $421 per night (USD)
Expedia
Great Family Vacation Rental.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $421 per night (USD)Expedia
- From $468 per night (USD)
VRBO
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO PERFECT, far from normal! This stunning 2 bedroom, 2.5 bathroom townhouse with private pool will check all the ...
From $468 per night (USD)VRBO
- From $332 per night (USD)
Expedia
Fairway Villa w/ Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $332 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Charming 'Boho Breeze' Retreat w/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $250 per night (USD)VRBO
- From $571 per night (USD)
Expedia
Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 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 $571 per night (USD)Expedia
- From $571 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 $571 per night (USD)VRBO
- From $608 per night (USD)
Expedia
Casa Capri Beautiful Tropical with 3 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 b ...
From $608 per night (USD)Expedia
- From $900 per night (USD)
VRBO
Luxurious, Elegant Home, Waterfront\nWith Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oasis getaway, 3 bedroom, 3 bath, including chefs kitchen. This home has all the amenities on the water, located in a q ...
From $900 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
*Ocean Memories is the perfect Key West Escape* Wake Up to Amazing Ocean Views Start your day in tranquility, waking u ...
From $703 per night (USD)Expedia
- From $364 per night (USD)
VRBO
COOL BREEZE @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** This community is loc ...
From $364 per night (USD)VRBO
- From $730 per night (USD)
Expedia
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 $730 per night (USD)Expedia
- From $1311 per night (USD)
VRBO
Parking, Pool & Waterfront - Springtide House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This lovely waterfront 4 bedroom, 4.5 bath home is perfect for those wanting to experience everything Key West ...
From $1311 per night (USD)VRBO
- From $1613 per night (USD)
Expedia
Parking, Pet Friendly, Pool, Dock - Suncoast House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: This waterfront 5 bedroom, 5.5 bath home is perfect for those ready to enjoy all that Key West offers. With a p ...
From $1613 per night (USD)Expedia
- From $1311 per night (USD)
VRBO
Parking, Pet Friendly, Pool & Dock - Aquaria House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This stunning waterfront 4 bedroom, 4.5 bath home is perfect for those looking to embrace all that Key West has ...
From $1311 per night (USD)VRBO
- From $1220 per night (USD)
Expedia
Waterfront, Private Heated Pool - Capmar House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This beautiful waterfront 4 bedroom, 4 bath home is ideal for those looking to savor all that Key West has to o ...
From $1220 per night (USD)Expedia
- From $1817 per night (USD)
VRBO
Waterfront Home w/ Pool & Boat Dock - Mirador House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: This gorgeous waterfront 5 bedroom, 5.5 bath home is perfect for those looking to enjoy all that Key West has t ...
From $1817 per night (USD)VRBO
- From $1591 per night (USD)
Expedia
Waterfront Wellness Home w/Pool - Evershore Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This waterfront 4 bedroom, 4 bath home boasts activity and relaxation for those looking to fully enjoy Key West ...
From $1591 per night (USD)Expedia
- From $1309 per night (USD)
VRBO
Waterfront Home, Heated Pool - The Seagate Estate
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This waterfront 4 bedroom, 4.5 bath home is perfect for those ready to enjoy all that Key West offers. With a p ...
From $1309 per night (USD)VRBO
- From $1466 per night (USD)
Expedia
Waterfront, Pool & Dock - Spindrift House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This beautiful waterfront 4 bedroom, 4 bath home is perfect for enjoying all that Key West has to offer. With a ...
From $1466 per night (USD)Expedia
- From $1634 per night (USD)
VRBO
Parking, Pool & Dock - Waterlane House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This inviting waterfront 4 bedroom, 4.5 bath home is the perfect getaway for those wanting to immerse themselve ...
From $1634 per night (USD)VRBO
- From $1710 per night (USD)
Expedia
Oceanfront Wellness home w/pool - Mastway House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This waterfront 4 bedroom, 4 bath home boasts activity and relaxation for those looking to fully enjoy Key West ...
From $1710 per night (USD)Expedia
- From $301 per night (USD)
VRBO
ISLAND TIME at Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Time***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome back ...
From $301 per night (USD)VRBO
- From $304 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $304 per night (USD)Expedia
- From $499 per night (USD)
VRBO
'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 $499 per night (USD)VRBO
- From $378 per night (USD)
Expedia
A DUCK ON THE GREEN at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $378 per night (USD)Expedia
- From $244 per night (USD)
VRBO
A PALM TREE PARADISE @ the Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Palm tree Paradise***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***Stay on the only 18-hole golf club in the Florida Key ...
From $244 per night (USD)VRBO
- From $312 per night (USD)
Expedia
A SANCTUARY HOME at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A Sanctuary Home*****PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***** | Stay on the only 18-hole golf club in the Florida ...
From $312 per night (USD)Expedia
- From $196 per night (USD)
VRBO
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 $196 per night (USD)VRBO
- From $231 per night (USD)
Expedia
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)Expedia
- From $507 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” located in sunny Key West, Florida on Stock Island. This spacious and accommodating 3 bed ...
From $507 per night (USD)VRBO
- From $233 per night (USD)
Expedia
2 Bedroom Townhome on Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $233 per night (USD)Expedia
- From $552 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
New Listing-Golf Course Charmer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
Click For PricingExpedia
- Click For Pricing
VRBO
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w/ Community Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Dreaming of va ...
Click For PricingVRBO
- Click For Pricing
Expedia
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You and your guests will have exclusive use of this 45 ft yacht all to yourselves. The yacht stays docked, the entire re ...
Click For PricingExpedia
- From $1792 per night (USD)
VRBO
Luxury Home w/ Heated Pool - The Windrose Estate
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: This newly designed 6 bedroom, 6 bath home is perfect for those looking to embrace all that Key West has to off ...
From $1792 per night (USD)VRBO
- Click For Pricing
Expedia
Coconut Mallory Resort in Key West - 2 Bedroom Condo/Marina/Gumbos Bar & Grill
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coconut Mallory Resort and Marina in Key West 2 Bedroom 2 Bath Condo partial fantasy fest 10/28/23 - 11/4-23 (Saturday t ...
Click For PricingExpedia
- From $227 per night (USD)
VRBO
Poolside tropical paradise in Key West! The Salty Conch
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...
From $227 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Gorgeous Waterfront Home - Haven House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: The Haven House is truly heavenly on the quiet residential canals in Key Haven. This home boasts a modern water ...
From $330 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Waterfront & Heated Pool - Awai's Floating Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience Key West in a new way: aboard a luxury houseboat! From watching sunrise on the dock to watching suns ...
From $595 per night (USD)VRBO
- From $1077 per night (USD)
Expedia
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 $1077 per night (USD)Expedia
- From $299 per night (USD)
VRBO
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 ...
From $299 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w/boat slip for rent
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $256 per night (USD)Expedia
- From $258 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 $258 per night (USD)VRBO
- From $301 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 $301 per night (USD)Expedia
- Click For Pricing
VRBO
Keys to Paradise by AvantStay | Balcony, Pool, Golf
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home is available for stays of 28 nights or longer. Welcome to Keys to Paradise, your Key West sanctuary nestled r ...
Click For PricingVRBO
- From $366 per night (USD)
Expedia
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire res ...
From $366 per night (USD)Expedia
- From $787 per night (USD)
VRBO
2BR Apt in Oceanview Resort w/ Sunset Cruises & Poolside Relaxation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $787 per night (USD)VRBO
- From $703 per night (USD)
Expedia
2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $703 per night (USD)Expedia
- From $351 per night (USD)
VRBO
Oceanview Balcony King Suite at Oceans Edge Key West, Sunset Cruises
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $351 per night (USD)VRBO
- From $291 per night (USD)
Expedia
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $291 per night (USD)Expedia
- From $394 per night (USD)
VRBO
Serene Retreat w/ Waterfront Balcony & Easy Access to Paddleboarding
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $394 per night (USD)VRBO
- From $367 per night (USD)
Expedia
Room in Coastal Resort w/ Oceanview - Six Pools & Pvt Oceanview Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $367 per night (USD)Expedia
- From $376 per night (USD)
VRBO
Elegant Resort Room w/ Paddleboards, Kayaks & Breathtaking Oceanviews
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $376 per night (USD)VRBO
- From $734 per night (USD)
Expedia
2 Suites 2 Queen w/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $734 per night (USD)Expedia
- From $340 per night (USD)
VRBO
Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $340 per night (USD)VRBO
- From $752 per night (USD)
Expedia
2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $752 per night (USD)Expedia
- From $823 per night (USD)
VRBO
2 Charming Oceanfront Rooms w/ Full-Service Marina & Bike Rentals - Pets Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $823 per night (USD)VRBO
- From $324 per night (USD)
Expedia
Comfortable Family Resort Room w/ Ocean Views, Kayak Rentals & Six Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $324 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w/boat slip rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $226 per night (USD)VRBO
- From $347 per night (USD)
Expedia
Tropical Tee Time Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to a stunning vacation rental in Key West, nestled on a picturesque golf course within an amazing resort. This pr ...
From $347 per night (USD)Expedia
- From $1932 per night (USD)
VRBO
Parking, Pool & Pet Friendly - Catchlight House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Welcome to your ultimate Key West getaway! This stunning 6-bed, 6.5-bath home perfectly blends comfort, style, ...
From $1932 per night (USD)VRBO
- From $411 per night (USD)
Expedia
Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $411 per night (USD)Expedia
- From $2315 per night (USD)
VRBO
Parking, Pool & Pet Friendly - Larkshine House
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 18
Summary: Welcome to Larkshine House in Lunara Bay, Key West—a perfect retreat for families and large groups! This 8-bedr ...
From $2315 per night (USD)VRBO
- From $675 per night (USD)
Expedia
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 $675 per night (USD)Expedia
- From $123 per night (USD)
VRBO
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community Nestled in the picturesque Key West Go ...
From $123 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Waterfront 5 Bedroom Mansion with Pool&Dock
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Bring your boat up to 3 ...
From $320 per night (USD)Expedia
- From $657 per night (USD)
VRBO
Key West Paradise 3-bedroom townhome w/large shared pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect for family getaways or group trips, this spacious townhome offers plenty of room for everyone to enjoy. It featu ...
From $657 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Private & Haven-ly pool home on boating canal
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
This Haven-ly Marina home is a picture perfect Keys escape. The 2 bed/2 bath main home and 1/1 casita is situated on a c ...
From $341 per night (USD)Expedia
- From $288 per night (USD)
VRBO
On the Bright Side of the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your serene retreat at The Key West Golf Club! This meticulously cared-for 3-bedroom, 3-bathroom townhome rad ...
From $288 per night (USD)VRBO
- From $1239 per night (USD)
Expedia
Spacious 52' Sailboat | 6 Cabins | Dockside Escape
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 10
Summary: Our Lagoon 52 offers a unique and memorable stay on the water while docked at the Perry Hotel & Marina. This ca ...
From $1239 per night (USD)Expedia
- From $315 per night (USD)
VRBO
CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the charm of “Old Key West” aboard Vita Felice, a Luxurious Vintage Yacht and a piece of American History. Thi ...
From $315 per night (USD)VRBO
- From $2805 per night (USD)
Expedia
The Starboard House at Solaire Lunara Bay
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 20
Summary: Explore a stunning new build with eight generous bedrooms and a private pool. This exceptional home offers top- ...
From $2805 per night (USD)Expedia
- 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 $258 per night (USD)
Expedia
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 $258 per night (USD)Expedia
- From $286 per night (USD)
VRBO
A Sunset Celebration at the Key West Golf Club - Photos Coming Soon!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This lovely, fully furnished, townhouse has three bedrooms that sleeps up to 6 and two full baths . The spacious upstair ...
From $286 per night (USD)VRBO
- From $472 per night (USD)
Expedia
Grand Admiral - 46’ 2 Cabin Yacht
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome aboard your private floating hotel room, docked at The Perry Hotel & Marina in Key West. This lovely vessel feat ...
From $472 per night (USD)Expedia
- From $291 per night (USD)
VRBO
Spacious 4-bedroom house with large family and dining room. BRAND NEW
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Stock Island, brand new 4-bedroom house. This delightful property features WiFi, washer/dryer, upgraded appl ...
From $291 per night (USD)VRBO
- From $385 per night (USD)
Expedia
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 $385 per night (USD)Expedia
- From $174 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Step into our Island Oasis! A very spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the cov ...
From $174 per night (USD)VRBO
- From $253 per night (USD)
Expedia
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 $253 per night (USD)Expedia
- From $1759 per night (USD)
VRBO
Ocean's Edge | Lux Resort | Concierge | Marina
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Oceans Edge Key West Hotel & Marina is a luxurious resort located on the serene Stock Island, just minutes from the vibr ...
From $1759 per night (USD)VRBO
- From $354 per night (USD)
Expedia
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 $354 per night (USD)Expedia
- From $565 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 $565 per night (USD)VRBO
- From $1736 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 $1736 per night (USD)Expedia
- From $398 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 $398 per night (USD)VRBO
- From $456 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 $456 per night (USD)Expedia
- From $285 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 $285 per night (USD)VRBO
- From $481 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 $481 per night (USD)Expedia
- From $810 per night (USD)
VRBO
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 $810 per night (USD)VRBO
- From $174 per night (USD)
Expedia
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)Expedia