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Holiday Rentals with Pools in Stock Island

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Bathrooms

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5 km
25 rentals in Stock Island.
Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps, holiday rental in Stock Island
Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps, holiday rental in Stock Island
Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps, holiday rental in Stock Island

Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Lobster Lagoon, holiday rental in Stock Island
Lobster Lagoon, holiday rental in Stock Island
Lobster Lagoon, holiday rental in Stock Island

Lobster Lagoon

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, All pools
More info
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Poolside Cottage #411, holiday rental in Stock Island
Poolside Cottage #411, holiday rental in Stock Island
Poolside Cottage #411, holiday rental in Stock Island

Poolside Cottage #411

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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ANGLER'S RETREAT * the Truman Annex, holiday rental in Stock Island
ANGLER'S RETREAT * the Truman Annex, holiday rental in Stock Island
ANGLER'S RETREAT * the Truman Annex, holiday rental in Stock Island

ANGLER'S RETREAT * the Truman Annex

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval, holiday rental in Stock Island
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval, holiday rental in Stock Island
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval, holiday rental in Stock Island

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Vacation Rental in Coral Hammock, holiday rental in Stock Island
Vacation Rental in Coral Hammock, holiday rental in Stock Island
Vacation Rental in Coral Hammock, holiday rental in Stock Island

Vacation Rental in Coral Hammock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800, holiday rental in Stock Island
Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800, holiday rental in Stock Island
Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800, holiday rental in Stock Island

Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony, holiday rental in Stock Island
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony, holiday rental in Stock Island
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony, holiday rental in Stock Island

Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK, holiday rental in Stock Island
Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK, holiday rental in Stock Island
Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK, holiday rental in Stock Island

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps, All pools
More info
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The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo, holiday rental in Stock Island
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo, holiday rental in Stock Island
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo, holiday rental in Stock Island

The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps, All pools
More info
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Coconut Mallory Resort and Marina, holiday rental in Stock Island
Coconut Mallory Resort and Marina, holiday rental in Stock Island
Coconut Mallory Resort and Marina, holiday rental in Stock Island

Coconut Mallory Resort and Marina

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit, holiday rental in Stock Island
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit, holiday rental in Stock Island
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit, holiday rental in Stock Island

70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po, holiday rental in Stock Island
Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po, holiday rental in Stock Island
Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po, holiday rental in Stock Island

Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island

Walk to Duval and Mallory Square!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value, holiday rental in Stock Island
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value, holiday rental in Stock Island
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value, holiday rental in Stock Island

Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island

Walk to Duval and Mallory Square!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island
Walk to Duval and Mallory Square!, holiday rental in Stock Island

Walk to Duval and Mallory Square!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas, holiday rental in Stock Island
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas, holiday rental in Stock Island
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas, holiday rental in Stock Island

Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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Hyatt Sunset Harbor, holiday rental in Stock Island
Hyatt Sunset Harbor, holiday rental in Stock Island
Hyatt Sunset Harbor, holiday rental in Stock Island

Hyatt Sunset Harbor

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island

Hyatt Windward Pointe

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Hyatt Sunset Harbor, holiday rental in Stock Island
Hyatt Sunset Harbor, holiday rental in Stock Island
Hyatt Sunset Harbor, holiday rental in Stock Island

Hyatt Sunset Harbor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
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Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island

Hyatt Windward Pointe

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island
Hyatt Windward Pointe, holiday rental in Stock Island

Hyatt Windward Pointe

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
Hyatt Beach House! Quiet Key West Location!, holiday rental in Stock Island
Hyatt Beach House! Quiet Key West Location!, holiday rental in Stock Island
Hyatt Beach House! Quiet Key West Location!, holiday rental in Stock Island

Hyatt Beach House! Quiet Key West Location!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Payment Protection
The following properties match some of your filters:
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, holiday rental in Stock Island
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, holiday rental in Stock Island
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St, holiday rental in Stock Island

Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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As seen on
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Casa Atlantica: A studio condo on the Atlantic shore of Key West, holiday rental in Stock Island
Casa Atlantica: A studio condo on the Atlantic shore of Key West, holiday rental in Stock Island
Casa Atlantica: A studio condo on the Atlantic shore of Key West, holiday rental in Stock Island

Casa Atlantica: A studio condo on the Atlantic shore of Key West

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Stock Island
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Stock Island
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Stock Island

YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Duval balcony - street suite, holiday rental in Stock Island
Duval balcony - street suite, holiday rental in Stock Island
Duval balcony - street suite, holiday rental in Stock Island

Duval balcony - street suite

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Key West Classic Yacht Charter, holiday rental in Stock Island
Key West Classic Yacht Charter, holiday rental in Stock Island
Key West Classic Yacht Charter, holiday rental in Stock Island

Key West Classic Yacht Charter

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, holiday rental in Stock Island
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, holiday rental in Stock Island
CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool, holiday rental in Stock Island

CLOSE TO PERFECT at Key West Golf Club - 2/2.5 w/ Private Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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As seen on
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Dog-friendly condo with pool & hot tub - walk or bike to beach, holiday rental in Stock Island
Dog-friendly condo with pool & hot tub - walk or bike to beach, holiday rental in Stock Island
Dog-friendly condo with pool & hot tub - walk or bike to beach, holiday rental in Stock Island

Dog-friendly condo with pool & hot tub - walk or bike to beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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As seen on
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Last Stop in Paradise, holiday rental in Stock Island
Last Stop in Paradise, holiday rental in Stock Island
Last Stop in Paradise, holiday rental in Stock Island

Last Stop in Paradise

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, holiday rental in Stock Island
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, holiday rental in Stock Island
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!, holiday rental in Stock Island

ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w/ Private Heated Pool!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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As seen on
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~FISH CAMP!~ Family friendly, canal front, monthly rental., holiday rental in Stock Island
~FISH CAMP!~ Family friendly, canal front, monthly rental., holiday rental in Stock Island
~FISH CAMP!~ Family friendly, canal front, monthly rental., holiday rental in Stock Island

~FISH CAMP!~ Family friendly, canal front, monthly rental.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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As seen on
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Curry House- 2nd Floor w/ Balcony! Room 1, holiday rental in Stock Island
Curry House- 2nd Floor w/ Balcony! Room 1, holiday rental in Stock Island
Curry House- 2nd Floor w/ Balcony! Room 1, holiday rental in Stock Island

Curry House- 2nd Floor w/ Balcony! Room 1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, holiday rental in Stock Island
Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, holiday rental in Stock Island
Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub, holiday rental in Stock Island

Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Florida Keys outpost, holiday rental in Stock Island
Florida Keys outpost, holiday rental in Stock Island
Florida Keys outpost, holiday rental in Stock Island

Florida Keys outpost

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Ground-level getaway with free WiFi, private deck, & shared outdoor pool, holiday rental in Stock Island
Ground-level getaway with free WiFi, private deck, & shared outdoor pool, holiday rental in Stock Island
Ground-level getaway with free WiFi, private deck, & shared outdoor pool, holiday rental in Stock Island

Ground-level getaway with free WiFi, private deck, & shared outdoor pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, holiday rental in Stock Island
Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, holiday rental in Stock Island
Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places, holiday rental in Stock Island

Beautiful Family-Sized Vacation House! 5 minute drive from Most Beautiful Places

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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As seen on
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The Queens Villa, holiday rental in Stock Island
The Queens Villa, holiday rental in Stock Island
The Queens Villa, holiday rental in Stock Island

The Queens Villa

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
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SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, holiday rental in Stock Island
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, holiday rental in Stock Island
SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!, holiday rental in Stock Island

SOUTHERNMOST SUNSHINE- 4 Bed/3 Bath- Old Town Key West w/ Pool & Parking!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, holiday rental in Stock Island
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, holiday rental in Stock Island
Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining, holiday rental in Stock Island

Tranquil tropical retreat with pool, private deck, & W/D - walk to bars/dining

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, holiday rental in Stock Island
Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, holiday rental in Stock Island
Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex, holiday rental in Stock Island

Shipyard 208-6 2 Bedroom 2 Bathroom in Truman Annex

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West, holiday rental in Stock Island
Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West, holiday rental in Stock Island
Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West, holiday rental in Stock Island

Soleil Chalet - 3 bedroom - private pool- Luxury living in Old Town Key West

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, holiday rental in Stock Island
Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, holiday rental in Stock Island
Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina, holiday rental in Stock Island

Middle Sunset: 3 Bedroom Luxury Condo at Bayfront Suites & Marina

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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A Palm Tree Haven in Key West *Pet Friendly*, holiday rental in Stock Island
A Palm Tree Haven in Key West *Pet Friendly*, holiday rental in Stock Island
A Palm Tree Haven in Key West *Pet Friendly*, holiday rental in Stock Island

A Palm Tree Haven in Key West *Pet Friendly*

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., holiday rental in Stock Island
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., holiday rental in Stock Island
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK  Stay., holiday rental in Stock Island

Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, holiday rental in Stock Island
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, holiday rental in Stock Island
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!, holiday rental in Stock Island

ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo in The Meadows!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH, holiday rental in Stock Island

BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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As seen on
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