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Key West Vacation Rentals

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5 km
120 rentals in Key West.
Key West Suites Hotel 205, vacation rental in Key West
Key West Suites Hotel 205, vacation rental in Key West
Key West Suites Hotel 205, vacation rental in Key West

Key West Suites Hotel 205

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Island Suite @ KW Vacation, vacation rental in Key West

Island Suite @ KW Vacation

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Eleanor's Place in Key West Old Town - Dogs Ok, vacation rental in Key West
Eleanor's Place in Key West Old Town - Dogs Ok, vacation rental in Key West
Eleanor's Place in Key West Old Town - Dogs Ok, vacation 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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Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West
Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West
Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West

Clean Apartment in Old Town Key West (Best Downtown Locations)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, vacation rental in Key West
OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, vacation rental in Key West
OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D, vacation rental in Key West

OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West
Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West
Clean Apartment in Old Town Key West (Best Downtown Locations), vacation rental in Key West

Clean Apartment in Old Town Key West (Best Downtown Locations)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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One-bedroom time share suite in the heart of Old Key West, vacation rental in Key West
One-bedroom time share suite in the heart of Old Key West, vacation rental in Key West
One-bedroom time share suite in the heart of Old Key West, vacation rental in Key West

One-bedroom time share suite in the heart of Old Key West

Condo/Apartment
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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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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Sweet Caroline Seaport Floor 2, vacation rental in Key West
Sweet Caroline Seaport Floor 2, vacation rental in Key West
Sweet Caroline Seaport Floor 2, vacation rental in Key West

Sweet Caroline Seaport Floor 2

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, vacation rental in Key West
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, vacation rental in Key West
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P, vacation rental in Key West

The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared P

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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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Truman Annex-Steps to Famous Duval Street, vacation rental in Key West
Truman Annex-Steps to Famous Duval Street, vacation rental in Key West
Truman Annex-Steps to Famous Duval Street, vacation rental in Key West

Truman Annex-Steps to Famous Duval Street

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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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Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, vacation rental in Key West
Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, vacation rental in Key West
Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort, vacation rental in Key West

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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Private, heated pool.  Private yard., vacation rental in Key West
Private, heated pool.  Private yard., vacation rental in Key West
Private, heated pool.  Private yard., vacation rental in Key West

Private, heated pool. Private yard.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Carriage House, vacation rental in Key West
Historic Carriage House, vacation rental in Key West
Historic Carriage House, vacation rental in Key West

Historic Carriage House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, vacation rental in Key West
Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, vacation rental in Key West
Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy, vacation rental in Key West

Cozy Key West Hideaway with a Pool, Digital Workspace, and Privacy

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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

Holiday Rental House
2 bedrooms
2 bathrooms
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, vacation rental in Key West
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, vacation rental in Key West
Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne, vacation rental in Key West

Tropical Old Town Bungalow: Charming 2nd Floor Unit, Private Spa/Shared Pool, Ne

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, vacation rental in Key West
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, vacation rental in Key West
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp, vacation rental in Key West

Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterp

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Bea, vacation rental in Key West
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Bea, vacation rental in Key West
Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Bea, vacation rental in Key West

Ella Varela: Gorgeous Conch Cottage in Key West's Heart, Close to Old Town & Bea

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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Lovely 2 bedroom, 2 bath condo at La Brisa., vacation rental in Key West
Lovely 2 bedroom, 2 bath condo at La Brisa., vacation rental in Key West
Lovely 2 bedroom, 2 bath condo at La Brisa., vacation rental in Key West

Lovely 2 bedroom, 2 bath condo at La Brisa.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, vacation rental in Key West
Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, vacation rental in Key West
Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry, vacation rental in Key West

Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to, vacation rental in Key West
Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to, vacation rental in Key West
Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to, vacation rental in Key West

Truman's Treasure: Beautifully Updated 2nd Floor Condo, Perfectly Convenient to

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Southernmost Beauty, vacation rental in Key West
Southernmost Beauty, vacation rental in Key West
Southernmost Beauty, vacation rental in Key West

Southernmost Beauty

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Nature's Boutique, vacation rental in Key West
Nature's Boutique, vacation rental in Key West
Nature's Boutique, vacation rental in Key West

Nature's Boutique

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, vacation rental in Key West
White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, vacation rental in Key West
White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do, vacation rental in Key West

White Ibis: Charming 2BR Key West Home, Pool, Ideal for Downtown & Beach Fun, Do

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from D, vacation rental in Key West
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from D, vacation rental in Key West
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from D, vacation rental in Key West

The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from D

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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 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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Key West Gulf front Home with private dock and pool.  , vacation rental in Key West
Key West Gulf front Home with private dock and pool.  , vacation rental in Key West
Key West Gulf front Home with private dock and pool.  , vacation rental in Key West

Key West Gulf front Home with private dock and pool.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart, vacation rental in Key West
Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart, vacation rental in Key West
Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart, vacation rental in Key West

Casa Sol: Discover This Charming, Pet-Friendly Key West Conch House in the Heart

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, vacation rental in Key West
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, vacation rental in Key West
Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t, vacation rental in Key West

Salt Ponds Sanctuary: Your Tranquil Escape, Shared Pool/Hot Tub & Proximity to t

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, vacation rental in Key West
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, vacation rental in Key West
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House, vacation rental in Key West

Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House

Holiday Rental House
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!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, vacation rental in Key West
Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, vacation rental in Key West
Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool, vacation rental in Key West

Ananda - Discover Your Blissful Getaway, Steps from Smathers Beach, Shared Pool

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, vacation rental in Key West
Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, vacation rental in Key West
Key West Bayfront Paradise - House and Private Pool!  Steps from shops and food, vacation rental in Key West

Key West Bayfront Paradise - House and Private Pool! Steps from shops and food

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Living On the Hook in Key West Harbour, vacation rental in Key West
Living On the Hook in Key West Harbour, vacation rental in Key West
Living On the Hook in Key West Harbour, vacation rental in Key West

Living On the Hook in Key West Harbour

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, vacation rental in Key West
Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, vacation rental in Key West
Nassau Suite just steps to Duval Tropical oasis  quiet location Downtown, vacation rental in Key West

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Artist Cottage, vacation rental in Key West
Artist Cottage, vacation rental in Key West
Artist Cottage, vacation rental in Key West

Artist Cottage

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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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Studio Blue, vacation rental in Key West
Studio Blue, vacation rental in Key West
Studio Blue, vacation rental in Key West

Studio Blue

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minu, vacation rental in Key West
Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minu, vacation rental in Key West
Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minu, vacation rental in Key West

Lotus Blossom: Discover Paradise, 3BR Home W/ Tropical Courtyard, Hot Tub & Minu

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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Showing results 1-50 of 120
Frequently Asked Questions about Key West






Key West Vacation Rentals
Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.
Where to rent in Key West, Florida
Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. 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.
Key West Bars and Restaurants
Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? 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.
Sightseeing and Activities in Key West
Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.