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Key West Romantic Vacation Rentals

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72 rentals in Key West.
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Verandah, vacation rental in Key West

Verandah

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Emma's Secret, vacation rental in Key West

Emma's Secret

2 bedrooms
1 bathroom
Sleeps 4
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Emma's Escape, vacation rental in Key West

Emma's Escape

2 bedrooms
1 bathroom
Sleeps 4
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A Place In Paradise, vacation rental in Key West

A Place In Paradise

2 bedrooms
2 bathrooms
Sleeps 6
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Linger Longer, vacation rental in Key West

Linger Longer

2 bedrooms
1 bathroom
Sleeps 5
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Conch Condo, vacation rental in Key West

Conch Condo

2 bedrooms
2 bathrooms
Sleeps 5
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A Siesta Bay, vacation rental in Key West

A Siesta Bay

2 bedrooms
1 bathroom
Sleeps 4
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Parrot Perch, vacation rental in Key West

Parrot Perch

2 bedrooms
2 bathrooms
Sleeps 5
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Shipyard Treasure, vacation rental in Key West

Shipyard Treasure

2 bedrooms
1 bathroom
Sleeps 4
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Key West Charming, vacation rental in Key West

Key West Charming

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Finn Key, vacation rental in Key West

Finn Key

2 bedrooms
1 bathroom
Sleeps 4
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Beach House Condo, vacation rental in Key West

Beach House Condo

2 bedrooms
2 bathrooms
Sleeps 5
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Papaya Place, vacation rental in Key West

Papaya Place

2 bedrooms
2 bathrooms
Sleeps 6
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Artist Garden, vacation rental in Key West

Artist Garden

2 bedrooms
2 bathrooms
Sleeps 4
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Key West Found, vacation rental in Key West

Key West Found

2 bedrooms
2 bathrooms
Sleeps 6
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Lavender Jungle, vacation rental in Key West

Lavender Jungle

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Duval Sea Turtle, vacation rental in Key West

Duval Sea Turtle

2 bedrooms
2 bathrooms
Sleeps 6
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Duval Breeze, vacation rental in Key West

Duval Breeze

2 bedrooms
2 bathrooms
Sleeps 6
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Key Lime Pie, vacation rental in Key West

Key Lime Pie

2 bedrooms
2 bathrooms
Sleeps 4
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Alluring Porches, vacation rental in Key West

Alluring Porches

3 bedrooms
3 bathrooms
Sleeps 6
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Paradise Place, vacation rental in Key West

Paradise Place

1 bedroom
1 bathroom
Sleeps 4
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Sunny View, vacation rental in Key West

Sunny View

1 bedroom
2 bathrooms
Sleeps 2
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Conch Wind, vacation rental in Key West

Conch Wind

2 bedrooms
2 bathrooms
Sleeps 4
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Ibis, vacation rental in Key West

Ibis

1 bedroom
1 bathroom
Sleeps 2
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Coconut Cottage, vacation rental in Key West

Coconut Cottage

1 bedroom
2 bathrooms
Sleeps 2
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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 **

1 bedroom
1 bathroom
Sleeps 4
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Easy Livin', vacation rental in Key West

Easy Livin'

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Atlantis House Master Suite, vacation rental in Key West

Atlantis House Master Suite

1 bedroom
1 bathroom
Sleeps 2
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5 other travelers have booked this property
Sundown Refuge, vacation rental in Key West

Sundown Refuge

2 bedrooms
2 bathrooms
Sleeps 5
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Coconut Beach, vacation rental in Key West

Coconut Beach

1 bedroom
2 bathrooms
Sleeps 4
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3 other travelers have booked this property
First Breath, vacation rental in Key West

First Breath

3 bedrooms
2 bathrooms
Sleeps 6
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The Dolphin House, vacation rental in Key West

The Dolphin House

4 bedrooms
3 bathrooms
Sleeps 8
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City Cay, vacation rental in Key West

City Cay

1 bedroom
1 bathroom
Sleeps 2
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737 The Place, a  Monthly Rental Old Town Key West, vacation rental in Key West

737 The Place, a Monthly Rental Old Town Key West

1 bedroom
1 bathroom
Sleeps 2
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1 other traveler has booked this property
Sunset Celebration, vacation rental in Key West

Sunset Celebration

2 bedrooms
1 bathroom
Sleeps 4
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Newton's Nest, vacation rental in Key West

Newton's Nest

1 bedroom
1 bathroom
Sleeps 2
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Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families, vacation rental in Key West

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

2 bedrooms
2 bathrooms
Sleeps 4
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Tropical Casita, vacation rental in Key West

Tropical Casita

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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SUMMER IS HERE...ENJOY THE BEST DEAL IN THE KEYS, vacation rental in Key West

SUMMER IS HERE...ENJOY THE BEST DEAL IN THE KEYS

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -, vacation rental in Key West

Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -

2 bedrooms
3 bathrooms
Sleeps 4
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'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!, vacation rental in Key West

'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!

2 bedrooms
3 bathrooms
Sleeps 6
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!, vacation rental in Key West

'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!

3 bedrooms
3 bathrooms
Sleeps 8
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!, vacation rental in Key West

'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

3 bedrooms
3 bathrooms
Sleeps 8
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'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!, vacation rental in Key West

'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!

1 bedroom
1 bathroom
Sleeps 4
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Attitude Key West (2 Bikes and Wireless Internet), vacation rental in Key West

Attitude Key West (2 Bikes and Wireless Internet)

2 bedrooms
1 bathroom
Sleeps 4
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval, vacation rental in Key West

'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval

3 bedrooms
3 bathrooms
Sleeps 8
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!, vacation rental in Key West

Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!

3 bedrooms
3 bathrooms
Sleeps 6
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Secret Villa I * Old Town with Private Pool, close to Duval!, vacation rental in Key West

Secret Villa I * Old Town with Private Pool, close to Duval!

3 bedrooms
3 bathrooms
Sleeps 6
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Atlantic Paradise, vacation rental in Key West

Atlantic Paradise

2 bedrooms
2 bathrooms
Sleeps 6
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*Stay on the ocean with fantastic view, luxury finishes at great prices*, vacation rental in Key West

*Stay on the ocean with fantastic view, luxury finishes at great prices*

2 bedrooms
2 bathrooms
Sleeps 6
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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!
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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.