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Stock Island
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Stock Island Holiday Rentals with Pools
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All pools (25)
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Kid friendly (24)
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Condominium/Apartment (17)
Holiday Rental House (8)
Cabin Holiday Rental (0)
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Water Views (17)
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Distance from
5 km
Sacred Space Gallery
Sea Monkey Ocean Adventures
Beards & Brews
Hillbilly Hookers Key West Fishing Charter
Boundless Charters Key West
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25 rentals
in Stock Island.
Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Lobster Lagoon
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps, All pools
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Poolside Cottage #411
2 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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As seen on
ANGLER'S RETREAT * the Truman Annex
5 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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As seen on
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Vacation Rental in Coral Hammock
10 reviews
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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As seen on
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps, All pools
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The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps, All pools
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Coconut Mallory Resort and Marina
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Walk to Duval and Mallory Square!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Walk to Duval and Mallory Square!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Walk to Duval and Mallory Square!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps, All pools
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Hyatt Sunset Harbor
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Hyatt Windward Pointe
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Hyatt Sunset Harbor
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, All pools
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Hyatt Windward Pointe
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Hyatt Windward Pointe
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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Hyatt Beach House! Quiet Key West Location!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, All pools
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The following properties match some of your filters:
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
77 reviews
Condo/Apartment
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0 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Casa Atlantica: A studio condo on the Atlantic shore of Key West
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
YKNOT CHARTERS, ON AND OFF DOCK CHARTERS
30 reviews
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Duval balcony - street suite
4 reviews
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Key West Classic Yacht Charter
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Dog-friendly condo with pool & hot tub - walk or bike to beach
58 reviews
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Last Stop in Paradise
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!
4 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
~FISH CAMP!~ Family friendly, canal front, monthly rental.
1 review
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Curry House- 2nd Floor w/ Balcony! Room 1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Florida Keys outpost
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
The Queens Villa
Holiday Rental House
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2 bedrooms
4 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina
7 reviews
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
A Palm Tree Haven in Key West *Pet Friendly*
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
2 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
1 review
Condo/Apartment
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
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As seen on
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