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Holiday Rentals in Key West

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116 rentals in Key West.
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, holiday rental in Key West

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), holiday rental in Key West

Casa Del Sol, a Key West Vacation (Truman Annex)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, holiday rental in Key West
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, holiday rental in Key West
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, holiday rental in Key West

LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BIG POOL! Across Street from Beach!  SEASIDE PLACE, Key West - 5/5 w/parking, holiday rental in Key West
BIG POOL! Across Street from Beach!  SEASIDE PLACE, Key West - 5/5 w/parking, holiday rental in Key West
BIG POOL! Across Street from Beach!  SEASIDE PLACE, Key West - 5/5 w/parking, holiday rental in Key West

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Simonton Studio, an Old Town get-away for 2, holiday rental in Key West
Simonton Studio, an Old Town get-away for 2, holiday rental in Key West
Simonton Studio, an Old Town get-away for 2, holiday rental in Key West

Simonton Studio, an Old Town get-away for 2

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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The Mermaids House, Historic Old Town Key West, holiday rental in Key West
The Mermaids House, Historic Old Town Key West, holiday rental in Key West
The Mermaids House, Historic Old Town Key West, holiday rental in Key West

The Mermaids House, Historic Old Town Key West

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, holiday rental in Key West

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, holiday rental in Key West

Henry's Piece Of Paradise On The Ocean In Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Harbor Walk Hideaways, holiday rental in Key West
Harbor Walk Hideaways, holiday rental in Key West
Harbor Walk Hideaways, holiday rental in Key West

Harbor Walk Hideaways

Private Room
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, holiday rental in Key West

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West
Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West
Sunrise at Seaside Condo 2 Bedroom, holiday rental in Key West

Sunrise at Seaside Condo 2 Bedroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Duval Balcony - Street Suite, holiday rental in Key West
Duval Balcony - Street Suite, holiday rental in Key West
Duval Balcony - Street Suite, holiday rental in Key West

Duval Balcony - Street Suite

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Artist Cottage in Truman Annex, holiday rental in Key West
Artist Cottage in Truman Annex, holiday rental in Key West
Artist Cottage in Truman Annex, holiday rental in Key West

Artist Cottage in Truman Annex

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, holiday rental in Key West

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Quiet, Quaint And Conveniently Located!, holiday rental in Key West
Quiet, Quaint And Conveniently Located!, holiday rental in Key West
Quiet, Quaint And Conveniently Located!, holiday rental in Key West

Quiet, Quaint And Conveniently Located!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, holiday rental in Key West
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, holiday rental in Key West
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, holiday rental in Key West

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Less than two blocks from the famous Duval St shuffle, holiday rental in Key West
Less than two blocks from the famous Duval St shuffle, holiday rental in Key West
Less than two blocks from the famous Duval St shuffle, holiday rental in Key West

Less than two blocks from the famous Duval St shuffle

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Listing Family Friendly , holiday rental in Key West
New Listing Family Friendly , holiday rental in Key West
New Listing Family Friendly , holiday rental in Key West

New Listing Family Friendly

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Key West
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Key West
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, holiday rental in Key West

YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Anchor Drop in Key West is a modern elegance with luxury finishes., holiday rental in Key West
Anchor Drop in Key West is a modern elegance with luxury finishes., holiday rental in Key West
Anchor Drop in Key West is a modern elegance with luxury finishes., holiday rental in Key West

Anchor Drop in Key West is a modern elegance with luxury finishes.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, holiday rental in Key West

6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Island vibe, Downtown Nightlife, Sunset, holiday rental in Key West
Island vibe, Downtown Nightlife, Sunset, holiday rental in Key West
Island vibe, Downtown Nightlife, Sunset, holiday rental in Key West

Island vibe, Downtown Nightlife, Sunset

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West
Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West
Comfy Family Home in a Gorgeous Gated Community, holiday rental in Key West

Comfy Family Home in a Gorgeous Gated Community

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, holiday rental in Key West

HISTORIC KEY WEST - Conch House - Sleeps 5

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, holiday rental in Key West

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret, holiday rental in Key West
Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret, holiday rental in Key West
Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret, holiday rental in Key West

Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes, holiday rental in Key West

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, holiday rental in Key West

The Tree House Old Town 2 Bedroom MONTHLY Rental

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, holiday rental in Key West

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Conch Haven Old Town 1/1 MONTHLY Rental, holiday rental in Key West
Conch Haven Old Town 1/1 MONTHLY Rental, holiday rental in Key West
Conch Haven Old Town 1/1 MONTHLY Rental, holiday rental in Key West

Conch Haven Old Town 1/1 MONTHLY Rental

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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BOOK NOW CONTEMPORARY LUXURY WITH STUNNING OCEAN VIEWS AMAZING VALUE, holiday rental in Key West
BOOK NOW CONTEMPORARY LUXURY WITH STUNNING OCEAN VIEWS AMAZING VALUE, holiday rental in Key West
BOOK NOW CONTEMPORARY LUXURY WITH STUNNING OCEAN VIEWS AMAZING VALUE, holiday rental in Key West

BOOK NOW CONTEMPORARY LUXURY WITH STUNNING OCEAN VIEWS AMAZING VALUE

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Vista, holiday rental in Key West
Ocean Vista, holiday rental in Key West
Ocean Vista, holiday rental in Key West

Ocean Vista

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, holiday rental in Key West

HISTORIC KEY WEST - Cigar House - Sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, holiday rental in Key West

HISTORIC KEY WEST - Turtle House - Sleeps 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, holiday rental in Key West

Seaside Condo 2 pools. sunny, quiet, near Old Town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunshine suit (2/2 apartment), holiday rental in Key West
Sunshine suit (2/2 apartment), holiday rental in Key West
Sunshine suit (2/2 apartment), holiday rental in Key West

Sunshine suit (2/2 apartment)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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HISTORIC KEY WEST  - Main House - Sleeps 8, holiday rental in Key West
HISTORIC KEY WEST  - Main House - Sleeps 8, holiday rental in Key West
HISTORIC KEY WEST  - Main House - Sleeps 8, holiday rental in Key West

HISTORIC KEY WEST - Main House - Sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Shipyard-1/2 Block Duval Street, holiday rental in Key West
Shipyard-1/2 Block Duval Street, holiday rental in Key West
Shipyard-1/2 Block Duval Street, holiday rental in Key West

Shipyard-1/2 Block Duval Street

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, holiday rental in Key West

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Key West Suites Hotel unit 201, holiday rental in Key West
Key West Suites Hotel unit 201, holiday rental in Key West
Key West Suites Hotel unit 201, holiday rental in Key West

Key West Suites Hotel unit 201

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., holiday rental in Key West
Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., holiday rental in Key West
Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., holiday rental in Key West

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxuriously upgraded Condo with Salty Breezes and Exquisite Sunrises, holiday rental in Key West
Luxuriously upgraded Condo with Salty Breezes and Exquisite Sunrises, holiday rental in Key West
Luxuriously upgraded Condo with Salty Breezes and Exquisite Sunrises, holiday rental in Key West

Luxuriously upgraded Condo with Salty Breezes and Exquisite Sunrises

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Deluxe One Bedroom Condo, holiday rental in Key West
Deluxe One Bedroom Condo, holiday rental in Key West
Deluxe One Bedroom Condo, holiday rental in Key West

Deluxe One Bedroom Condo

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West
A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West
A Change in Latitudes - TRUMAN ANNEX, holiday rental in Key West

A Change in Latitudes - TRUMAN ANNEX

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BOOK TODAY AND ENJOY YOUR KEY WEST  ISLAND OASIS CONDO ON THE OCEAN, holiday rental in Key West
BOOK TODAY AND ENJOY YOUR KEY WEST  ISLAND OASIS CONDO ON THE OCEAN, holiday rental in Key West
BOOK TODAY AND ENJOY YOUR KEY WEST  ISLAND OASIS CONDO ON THE OCEAN, holiday rental in Key West

BOOK TODAY AND ENJOY YOUR KEY WEST ISLAND OASIS CONDO ON THE OCEAN

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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'Little Paradise' Historic Seaport Old Town Key West , holiday rental in Key West
'Little Paradise' Historic Seaport Old Town Key West , holiday rental in Key West
'Little Paradise' Historic Seaport Old Town Key West , holiday rental in Key West

'Little Paradise' Historic Seaport Old Town Key West

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sizzling Summer and Fall Specials for your ocean view Key West Oasis, holiday rental in Key West
Sizzling Summer and Fall Specials for your ocean view Key West Oasis, holiday rental in Key West
Sizzling Summer and Fall Specials for your ocean view Key West Oasis, holiday rental in Key West

Sizzling Summer and Fall Specials for your ocean view Key West Oasis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean., holiday rental in Key West
Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean., holiday rental in Key West
Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean., holiday rental in Key West

Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View, holiday rental in Key West

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Eleanor's Place in Key West Old Town - Dogs Ok, holiday rental in Key West
Eleanor's Place in Key West Old Town - Dogs Ok, holiday rental in Key West
Eleanor's Place in Key West Old Town - Dogs Ok, holiday rental in Key West

Eleanor's Place in Key West Old Town - Dogs Ok

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 116
Frequently Asked Questions about Key West