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

$TORTUGA HAMMOCK -2 Bedroom\/ 2.5 Bathroom Townhouse with Shared Pool & Parking$
From $687 per night (USD)
VRBO
TORTUGA HAMMOCK -2 Bedroom\/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Bedrooms:
3
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 $687 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Upscale Townhouse with Golf and Lake Views, Shared Pool, WiFi, and AC - Dogs OK
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Tipsy Mermaid Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $287 per night (USD)
Expedia
From $805 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 $805 per night (USD)
VRBO
$Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, pool$
From $233 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 $233 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Joan's Caribbean Hideaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $313 per night (USD)
VRBO
From $798 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 $798 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 $193 per night (USD)
Expedia
Paradise found at the Key West Golf Club!
Bedrooms:
2
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)
Expedia
From $831 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 $831 per night (USD)
VRBO
$Family home in gated community w\/great amenities, shared pool, fitness center$
From $781 per night (USD)
Expedia
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 $781 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Great Family Vacation Rental.
Bedrooms:
3
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 $539 per night (USD)
VRBO
$CLOSE TO PERFECT at Key West Golf Club - 2\/2.5 w\/ Private Pool$
From $467 per night (USD)
Expedia
CLOSE TO PERFECT at Key West Golf Club - 2\/2.5 w\/ Private Pool
Bedrooms:
3
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 $467 per night (USD)
Expedia
$Fairway Villa w\/ Private Pool$
From $247 per night (USD)
VRBO
Fairway Villa w\/ Private Pool
Bedrooms:
3
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 $247 per night (USD)
VRBO
$Charming 'Boho Breeze' Retreat w\/ Pool Access$
From $169 per night (USD)
Expedia
Charming 'Boho Breeze' Retreat w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $169 per night (USD)
Expedia
From $815 per night (USD)
VRBO
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 $815 per night (USD)
VRBO
From $815 per night (USD)
Expedia
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 $815 per night (USD)
Expedia
From $833 per night (USD)
VRBO
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 $833 per night (USD)
VRBO
$Luxurious, Elegant Home, Waterfront\nWith Dockage$
From $1073 per night (USD)
Expedia
Luxurious, Elegant Home, Waterfront\nWith Dockage
Bedrooms:
3
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 $1073 per night (USD)
Expedia
From $703 per night (USD)
VRBO
2-bedroom Oceanfront Condo next to Marina & 5-Star Restaurant
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Ocean Memories is the perfect Escape* Wake Up to Spectacular Ocean Views Start your day in tranquility, waking up to ...
From $703 per night (USD)
VRBO
From $419 per night (USD)
Expedia
COOL BREEZE @ the Key West Golf Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $419 per night (USD)
Expedia
From $899 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 condo. Watch the sunrise over the ocean ...
From $899 per night (USD)
VRBO
From $2658 per night (USD)
Expedia
Parking, Pool & Waterfront - Springtide House
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summary: This lovely waterfront 4 bedroom, 4.5 bath home is perfect for those wanting to experience everything Key West ...
From $2658 per night (USD)
Expedia
From $2754 per night (USD)
VRBO
Parking, Pet Friendly, Pool, Dock - Suncoast House
Bedrooms:
6
Bathrooms:
6
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 $2754 per night (USD)
VRBO
From $1735 per night (USD)
Expedia
Parking, Pet Friendly, Pool & Dock - Aquaria House
Bedrooms:
5
Bathrooms:
5
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 $1735 per night (USD)
Expedia
From $2350 per night (USD)
VRBO
Waterfront, Private Heated Pool - Capmar House
Bedrooms:
5
Bathrooms:
5
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 $2350 per night (USD)
VRBO
From $2753 per night (USD)
Expedia
Parking, Pet Friendly, Pool & Dock - Mirador House
Bedrooms:
6
Bathrooms:
6
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 $2753 per night (USD)
Expedia
From $2621 per night (USD)
VRBO
Parking, Pool & Dock - Evershore House
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: This waterfront 4 bedroom, 4 bath home is the ideal getaway for those looking to fully enjoy Key West. Featurin ...
From $2621 per night (USD)
VRBO
From $2387 per night (USD)
Expedia
Parking, Heated Pool, Pet Friendly - Seagate House
Bedrooms:
5
Bathrooms:
5
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 $2387 per night (USD)
Expedia
From $2064 per night (USD)
VRBO
Parking, Pool & Dock - Spindrift House
Bedrooms:
4
Bathrooms:
5
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 $2064 per night (USD)
VRBO
From $2548 per night (USD)
Expedia
Parking, Pool & Dock - Waterlane House
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summary: This inviting waterfront 4 bedroom, 4.5 bath home is the perfect getaway for those wanting to immerse themselve ...
From $2548 per night (USD)
Expedia
From $2547 per night (USD)
VRBO
Parking, Pool & Dock - Mastway House
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: This beautiful waterfront 4 bedroom, 4 bath home is ideal for those looking to savor all that Key West has to o ...
From $2547 per night (USD)
VRBO
From $351 per night (USD)
Expedia
ISLAND TIME at Key West Golf Club
Bedrooms:
3
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 $351 per night (USD)
Expedia
From $349 per night (USD)
VRBO
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 $349 per night (USD)
VRBO
From $619 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 $619 per night (USD)
Expedia
From $380 per night (USD)
VRBO
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 $380 per night (USD)
VRBO
From $306 per night (USD)
Expedia
A PALM TREE PARADISE @ the Key West Golf Club
Bedrooms:
2
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 $306 per night (USD)
Expedia
From $513 per night (USD)
VRBO
A SANCTUARY HOME at the Key West Golf Club
Bedrooms:
3
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 $513 per night (USD)
VRBO
$GOLF VILLA - Monthly Rental - 2BD\/2BA -Community Pool - RealKeyWest$
From $265 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 $265 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Poolside townhouse in Key West Golf Club
Bedrooms:
3
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
$The Flight Deck - 3 Bedroom \/ 3 Bathroom with Shared Pool & Fitness Center!$
From $661 per night (USD)
Expedia
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 $661 per night (USD)
Expedia
From $233 per night (USD)
VRBO
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)
VRBO
From $499 per night (USD)
Expedia
Key West Home on Deep Water Canal with Pool at Mile Marker 5, Fisherman's Dream
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your private oasis in the heart of Key West! This charming 3-bedroom 2 bathroom vacation home offers the perf ...
From $499 per night (USD)
Expedia
From $238 per night (USD)
VRBO
New Listing-Golf Course Charmer!
Bedrooms:
2
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 ...
From $238 per night (USD)
VRBO
$**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…$
From $368 per night (USD)
Expedia
**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 ...
From $368 per night (USD)
Expedia
From $481 per night (USD)
VRBO
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 ...
From $481 per night (USD)
VRBO
From $3211 per night (USD)
Expedia
Parking, Pet Friendly, Pool - Windrose House
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 $3211 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Hyatt Beach House, Two Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A tropical getaway in classic Key West style Hyatt Vacation Club at Beach House has 74 well-appointed luxury units off ...
From $304 per night (USD)
VRBO
$Coconut Mallory Resort in Key West - 2 Bedroom Condo\/Marina\/Gumbos Bar & Grill$
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 Pricing
Expedia
From $227 per night (USD)
VRBO
Poolside tropical paradise in Key West! The Salty Conch
Bedrooms:
2
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 $627 per night (USD)
Expedia
Private Parking & Waterfront - 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 $627 per night (USD)
Expedia
From $992 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 $992 per night (USD)
VRBO
$Amazing 4 Bdrm, 4 Bath Catamaran - Purpus\n$
From $1124 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 $1124 per night (USD)
Expedia
$Key Haven 3bedroom 2bath canal front home w\/boat dock, private pool, parking$
From $382 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 $382 per night (USD)
VRBO
$Mariner's Oasis at Sunset Marina- 2bed 2 bath condo w\/boat slip for rent$
From $353 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 $353 per night (USD)
Expedia
From $570 per night (USD)
VRBO
Gorgeous 53’ Hatteras yacht on Safe Harbor Channel.
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Stay on this gorgeous 53’ Hatteras yacht with cherry wood throughout and a huge salon with everything you need to relax ...
From $570 per night (USD)
VRBO
$Key West Home on Golf Course w\/ Patio & Grill!$
From $246 per night (USD)
Expedia
Key West Home on Golf Course w\/ Patio & Grill!
Bedrooms:
2
Bathrooms:
3
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 $246 per night (USD)
Expedia
From $770 per night (USD)
VRBO
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 $770 per night (USD)
VRBO
$2BR Apt in Oceanview Resort w\/ Sunset Cruises & Poolside Relaxation$
From $1556 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 $1556 per night (USD)
VRBO
From $1400 per night (USD)
VRBO
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 $1400 per night (USD)
VRBO
From $700 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 $700 per night (USD)
VRBO
From $560 per night (USD)
VRBO
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 $560 per night (USD)
VRBO
$Serene Retreat w\/ Waterfront Balcony & Easy Access to Paddleboarding$
From $777 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 $777 per night (USD)
VRBO
$Room in Coastal Resort w\/ Oceanview - Six Pools & Pvt Oceanview Balcony$
From $712 per night (USD)
VRBO
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 $712 per night (USD)
VRBO
$Elegant Resort Room w\/ Paddleboards, Kayaks & Breathtaking Oceanviews$
From $746 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 $746 per night (USD)
VRBO
$2 Suites 2 Queen w\/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools$
From $1425 per night (USD)
VRBO
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 $1425 per night (USD)
VRBO
From $672 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 $672 per night (USD)
VRBO
From $1493 per night (USD)
VRBO
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 $1493 per night (USD)
VRBO
From $371 per night (USD)
Expedia
New Property! An Island Siesta
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This lovely, fully furnished, townhouse has two bedrooms that sleeps up to 6 and two full baths . The spacious upstairs ...
From $371 per night (USD)
Expedia
From $367 per night (USD)
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 ...
From $367 per night (USD)
VRBO
$2 Charming Oceanfront Rooms w\/ Full-Service Marina & Bike Rentals - Pets Welcome$
From $1583 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 $1583 per night (USD)
VRBO
$Comfortable Family Resort Room w\/ Ocean Views, Kayak Rentals & Six Pools$
From $623 per night (USD)
VRBO
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 $623 per night (USD)
VRBO
$Ocean Oasis at Sunset Marina-2 bed 2 bath oceanfront condo w\/boat slip rental$
From $248 per night (USD)
Expedia
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 $248 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Tropical Tee Time Villa
Bedrooms:
4
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 $327 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Casa Del Mar in Beautiful Key west. Amazing open water view!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience Key West like a local in this charming 4-bedroom house. With 1 king bed, 2 queen beds, and 1 twin bed, guests ...
From $263 per night (USD)
Expedia
From $3518 per night (USD)
VRBO
Parking, Pool & Pet Friendly - Catchlight House
Bedrooms:
7
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 $3518 per night (USD)
VRBO
From $791 per night (USD)
VRBO
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 $791 per night (USD)
VRBO
From $4346 per night (USD)
VRBO
Parking, Pool & Pet Friendly - Larkshine House
Bedrooms:
9
Bathrooms:
8
Sleeps:
18
Summary: Welcome to Larkshine House in Key Haven Estates, Key West—a perfect retreat for families and large groups! This ...
From $4346 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Changes In Latitude
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to coastal perfection at this upscale waterfront retreat in Key Haven, just minutes from Old Town Key West and Du ...
From $541 per night (USD)
Expedia
From $683 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 $683 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Cabana at the Golf Club-Monthly Rental Charming 2-Bedroom Golf Course Retreat
Bedrooms:
2
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 $439 per night (USD)
Expedia
From $597 per night (USD)
VRBO
Waterfront 5 Bedroom Mansion with Pool&Dock
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Escape to a luxurious waterfront oasis located at Key Haven, just a stone's throw from Key West. Nring your boat up to 4 ...
From $597 per night (USD)
VRBO
From $330 per night (USD)
VRBO
Island Oasis-2 Bedroom Townhouse in the Gated Community of the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Step into this spacious 2-bedroom, 1 1/2 -bathroom home, perfect for your island getaway, in the gated community of the ...
From $330 per night (USD)
VRBO
From $368 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
3
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 $368 per night (USD)
VRBO
From $1452 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 $1452 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Modern Houseboat Oasis, 1BD, WiFi & AC - Writer’s Block in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome aboard the Writer's Block! A Houseboat, where the gentle lull of the waves inspires creativity and ignites the i ...
From $527 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Luxury Houseboat, 1BD WiFi & AC Oasis @ The Perry, Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to the Enchantress. This modern houseboat has been handcrafted to provide a warm and wholehearted True Key West ...
From $522 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary!$
From $436 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 $436 per night (USD)
VRBO
From $1744 per night (USD)
VRBO
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 $1744 per night (USD)
VRBO
$3 Bedroom 2 Bath Oceanfront Condo quiet and secluded adjacent to Hotel\/Marina$
From $655 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 $655 per night (USD)
VRBO
From $536 per night (USD)
VRBO
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 $536 per night (USD)
VRBO
From $735 per night (USD)
VRBO
CORAL CABANA ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
WELCOME BOATING AND GOLFING ENTHUSIASTS.. Located just off Key West at mile marker 5, the gated community of Coral Hammo ...
From $735 per night (USD)
VRBO
From $732 per night (USD)
Expedia
CASA DE VINO ~ Amazing Price for Charming Townhouse with Pool & Tiki!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING.. Located just off Key West at mile marker 5, the picturesque community of ...
From $732 per night (USD)
Expedia
From $579 per night (USD)
VRBO
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
IDEAL LOCATION FOR BOATERS AND GOLFERS... Located just off Key West at mile marker 5, the picturesque community of Coral ...
From $579 per night (USD)
VRBO
From $835 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 $835 per night (USD)
VRBO
From $174 per night (USD)
VRBO
Home away from home!
Bedrooms:
2
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 $302 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 $302 per night (USD)
VRBO
From $396 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 $396 per night (USD)
VRBO
$Luxury 2\/2 1\/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED$
From $551 per night (USD)
Expedia
Luxury 2\/2 1\/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Bedrooms:
3
Bathrooms:
3
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 $551 per night (USD)
Expedia
From $677 per night (USD)
VRBO
Ocean views! <br>I didn’t do it too
Bedrooms:
2
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 $677 per night (USD)
VRBO
From $769 per night (USD)
VRBO
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Bedrooms:
4
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 $769 per night (USD)
VRBO

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