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Key West Vacation Rentals

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111 rentals in Key West.
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, vacation rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, vacation rental in Key West
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths, vacation rental in Key West

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Summer  2022 gaps  Enchanting garden view on the Ocean- Fantastic Value, vacation rental in Key West
Summer  2022 gaps  Enchanting garden view on the Ocean- Fantastic Value, vacation rental in Key West
Summer  2022 gaps  Enchanting garden view on the Ocean- Fantastic Value, vacation rental in Key West

Summer 2022 gaps Enchanting garden view on the Ocean- Fantastic Value

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Ocean Vista, vacation rental in Key West
Ocean Vista, vacation rental in Key West
Ocean Vista, vacation rental in Key West

Ocean Vista

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Artist Cottage in Truman Annex, vacation rental in Key West
Artist Cottage in Truman Annex, vacation rental in Key West
Artist Cottage in Truman Annex, vacation rental in Key West

Artist Cottage in Truman Annex

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Del Sol, a Key West Vacation (Truman Annex), vacation rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), vacation rental in Key West
Casa Del Sol, a Key West Vacation (Truman Annex), vacation rental in Key West

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Seaside Place Key West FL 5 Bedroom House 4 Baths, vacation rental in Key West
Seaside Place Key West FL 5 Bedroom House 4 Baths, vacation rental in Key West
Seaside Place Key West FL 5 Bedroom House 4 Baths, vacation rental in Key West

Seaside Place Key West FL 5 Bedroom House 4 Baths

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Mermaids House, Historic Old Town Key West, vacation rental in Key West
The Mermaids House, Historic Old Town Key West, vacation rental in Key West
The Mermaids House, Historic Old Town Key West, vacation rental in Key West

The Mermaids House, Historic Old Town Key West

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, vacation rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, vacation rental in Key West
Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage, vacation 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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Simonton Studio, an Old Town get-away for 2, vacation rental in Key West
Simonton Studio, an Old Town get-away for 2, vacation rental in Key West
Simonton Studio, an Old Town get-away for 2, vacation 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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Henry's Piece Of Paradise On The Ocean In Key West, vacation rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, vacation rental in Key West
Henry's Piece Of Paradise On The Ocean In Key West, vacation 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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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, vacation rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, vacation rental in Key West
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida, vacation 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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Harbor Walk Hideaways, vacation rental in Key West
Harbor Walk Hideaways, vacation rental in Key West
Harbor Walk Hideaways, vacation rental in Key West

Harbor Walk Hideaways

Private Room
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sunrise at Seaside Condo 2 Bedroom, vacation rental in Key West
Sunrise at Seaside Condo 2 Bedroom, vacation rental in Key West
Sunrise at Seaside Condo 2 Bedroom, vacation rental in Key West

Sunrise at Seaside Condo 2 Bedroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, vacation rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, vacation rental in Key West
KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI, vacation 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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Duval Balcony - Street Suite, vacation rental in Key West
Duval Balcony - Street Suite, vacation rental in Key West
Duval Balcony - Street Suite, vacation rental in Key West

Duval Balcony - Street Suite

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, vacation rental in Key West
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, vacation rental in Key West
Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE, vacation 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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New Listing Family Friendly , vacation rental in Key West
New Listing Family Friendly , vacation rental in Key West
New Listing Family Friendly , vacation rental in Key West

New Listing Family Friendly

Rental Home
3 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, vacation rental in Key West
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, vacation rental in Key West
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH, vacation 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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Less than two blocks from the famous Duval St shuffle, vacation rental in Key West
Less than two blocks from the famous Duval St shuffle, vacation rental in Key West
Less than two blocks from the famous Duval St shuffle, vacation 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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Quiet, Quaint And Conveniently Located!, vacation rental in Key West
Quiet, Quaint And Conveniently Located!, vacation rental in Key West
Quiet, Quaint And Conveniently Located!, vacation rental in Key West

Quiet, Quaint And Conveniently Located!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Key West
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Key West
YKNOT CHARTERS,  ON AND OFF DOCK CHARTERS, vacation rental in Key West

YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

Rental Home
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, vacation rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, vacation rental in Key West
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location, vacation rental in Key West

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

Rental Home
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town, vacation rental in Key West
Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town, vacation rental in Key West
Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town, vacation rental in Key West

Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Key West Golf Club - Completely Renovated - Tree House Too., vacation rental in Key West
Key West Golf Club - Completely Renovated - Tree House Too., vacation rental in Key West
Key West Golf Club - Completely Renovated - Tree House Too., vacation rental in Key West

Key West Golf Club - Completely Renovated - Tree House Too.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Comfy Family Home in a Gorgeous Gated Community, vacation rental in Key West
Comfy Family Home in a Gorgeous Gated Community, vacation rental in Key West
Comfy Family Home in a Gorgeous Gated Community, vacation rental in Key West

Comfy Family Home in a Gorgeous Gated Community

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Island vibe, Downtown Nightlife, Evening sunsets, Beachside afternoons., vacation rental in Key West
Island vibe, Downtown Nightlife, Evening sunsets, Beachside afternoons., vacation rental in Key West
Island vibe, Downtown Nightlife, Evening sunsets, Beachside afternoons., vacation rental in Key West

Island vibe, Downtown Nightlife, Evening sunsets, Beachside afternoons.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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HISTORIC KEY WEST  - Conch House - Sleeps 5, vacation rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, vacation rental in Key West
HISTORIC KEY WEST  - Conch House - Sleeps 5, vacation rental in Key West

HISTORIC KEY WEST - Conch House - Sleeps 5

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **, vacation rental in Key West
** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **, vacation rental in Key West
** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **, vacation rental in Key West

** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Conch Haven Old Town 1/1 MONTHLY Rental, vacation rental in Key West
Conch Haven Old Town 1/1 MONTHLY Rental, vacation rental in Key West
Conch Haven Old Town 1/1 MONTHLY Rental, vacation 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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The Tree House Old Town 2 Bedroom MONTHLY Rental, vacation rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, vacation rental in Key West
The Tree House Old Town 2 Bedroom MONTHLY Rental, vacation rental in Key West

The Tree House Old Town 2 Bedroom MONTHLY Rental

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, vacation rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, vacation rental in Key West
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean, vacation 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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Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, vacation rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, vacation rental in Key West
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean, vacation 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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Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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HISTORIC KEY WEST -  Cigar House - Sleeps 4, vacation rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, vacation rental in Key West
HISTORIC KEY WEST -  Cigar House - Sleeps 4, vacation rental in Key West

HISTORIC KEY WEST - Cigar House - Sleeps 4

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunshine suit (2/2 apartment), vacation rental in Key West
Sunshine suit (2/2 apartment), vacation rental in Key West
Sunshine suit (2/2 apartment), vacation rental in Key West

Sunshine suit (2/2 apartment)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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 Seaside Condo 2 pools. sunny, quiet, near Old Town, vacation rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, vacation rental in Key West
 Seaside Condo 2 pools. sunny, quiet, near Old Town, vacation 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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HISTORIC KEY WEST - Turtle House - Sleeps 6, vacation rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, vacation rental in Key West
HISTORIC KEY WEST - Turtle House - Sleeps 6, vacation rental in Key West

HISTORIC KEY WEST - Turtle House - Sleeps 6

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Key West Suites Hotel unit 201, vacation rental in Key West
Key West Suites Hotel unit 201, vacation rental in Key West
Key West Suites Hotel unit 201, vacation rental in Key West

Key West Suites Hotel unit 201

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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HISTORIC KEY WEST  - Main House - Sleeps 8, vacation rental in Key West
HISTORIC KEY WEST  - Main House - Sleeps 8, vacation rental in Key West
HISTORIC KEY WEST  - Main House - Sleeps 8, vacation rental in Key West

HISTORIC KEY WEST - Main House - Sleeps 8

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

Shipyard-1/2 Block Duval Street

Rental Home
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, vacation rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, vacation rental in Key West
Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach, vacation rental in Key West

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Salty Breezes, Exquisite Sunrises & a luxuriously upgraded Condo in Key West., vacation rental in Key West
Salty Breezes, Exquisite Sunrises & a luxuriously upgraded Condo in Key West., vacation rental in Key West
Salty Breezes, Exquisite Sunrises & a luxuriously upgraded Condo in Key West., vacation rental in Key West

Salty Breezes, Exquisite Sunrises & a luxuriously upgraded Condo in Key West.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., vacation rental in Key West
Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., vacation rental in Key West
Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home., vacation rental in Key West

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Deluxe One Bedroom Condo, vacation rental in Key West
Deluxe One Bedroom Condo, vacation rental in Key West
Deluxe One Bedroom Condo, vacation 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, vacation rental in Key West
A Change in Latitudes - TRUMAN ANNEX, vacation rental in Key West
A Change in Latitudes - TRUMAN ANNEX, vacation rental in Key West

A Change in Latitudes - TRUMAN ANNEX

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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>, vacation rental in Key West
>, vacation rental in Key West
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Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Little Paradise' Historic Seaport Old Town Key West , vacation rental in Key West
'Little Paradise' Historic Seaport Old Town Key West , vacation rental in Key West
'Little Paradise' Historic Seaport Old Town Key West , vacation rental in Key West

'Little Paradise' Historic Seaport Old Town Key West

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW LISTING!  40’ Luxury Catamaran Yacht!, vacation rental in Key West
NEW LISTING!  40’ Luxury Catamaran Yacht!, vacation rental in Key West
NEW LISTING!  40’ Luxury Catamaran Yacht!, vacation rental in Key West

NEW LISTING! 40’ Luxury Catamaran Yacht!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Frequently Asked Questions about Key West





Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
More
Key West Vacation Rentals and Condos
Browse through the list of beachfront house rentals in the Florida Keys and you’ll start to feel the warm breeze. You’ll sense the cool sand under your feet and taste the spike of a margarita. Everyone and everything on the island of Key West seems to go at its own pace, which makes it a wondrous vacation destination for families and friends of all ages. House and condo rentals abound – penthouse beach villas on the sandy shoreline, inland cottages in the bustling Old Town district, even fully equipped yachts are available for stay!
Where To Rent a Vacation Home in Key West
Vacation rentals in Key West can be found all over town, but knowing what each area offers will help you decide on the perfect place. Condo rentals in Old Town will put you in the center of the action – steps from the famous Duval Street, with numerous restaurants, bars, boutiques, souvenir shops and major attractions. Luxurious, modern house rentals on the beach offer more privacy and relaxation. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.
Many House Rentals Near Attractions and Activities For All Ages
Key West vacation rentals scatter the whole island, so you’ll always be close to family fun and adventure. Fury Water Adventures offers jet skis, kayaking, parasailing, boating and some of the best snorkeling and diving excursions you’ll ever find. Fishermen will marvel at the eclectic aquatic life in the crystal-blue waters, while families can take the kids to the Florida Keys Eco-Discovery Center, with interactive and dynamic sea exhibits – all just steps away from the island’s spacious, family-friendly condo rentals. Enjoy the romance of paradise on a sunset dinner cruise to wind down from a busy day on the beach or in town.
Key West Bars and Restaurants
Bustling nightlife and gastronomy surround the house rentals in the Historic Seaport neighborhood. Start your night with frozen daiquiris at the famous Lazy Gecko before moving to the award-winning Italian restaurant La Trattoria on the legendary Duval Street. A visit to Key West wouldn’t be complete without trying the conch fritters. And we recommend you indulge in as many different versions of key lime pie as possible. Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.
Book a Key West Vacation Rental For Your Next Trip
Vacation rentals in Key West are the perfect way to experience the island like a local. Traipse down Duval Street to take in the culture, enjoy the family-friendly attractions with your children and loved ones and relax on the white-sand beaches with a margarita in hand. Whichever way you vacation, TripAdvisor has the best deals on house rentals, condo rentals, and beach homes in Key West.