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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)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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

Holiday Rental House
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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
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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
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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
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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

Holiday Rental House
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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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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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

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
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

Holiday Rental House
0 bedrooms
1 bathroom
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.

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
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 **

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
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

Holiday Rental House
2 bedrooms
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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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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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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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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.

Holiday Rental House
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
More info
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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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Amazingly Transformed in 2022 - Luxurious renovation, Fantastic Ocean View., vacation rental in Key West
Amazingly Transformed in 2022 - Luxurious renovation, Fantastic Ocean View., vacation rental in Key West
Amazingly Transformed in 2022 - Luxurious renovation, Fantastic Ocean View., vacation 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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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.
More
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.