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Key West Vacation Rentals

1 - 42 of 71 rentals
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Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
230 190 190 190 190 190 190 195 195 195 195 195 195 195 195 195 195
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - 180 225 225 225 215 - - - - - -
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - 220 230 220 - - - 220 230
Duval Hideaway: Cigar Maker's Cottage - Key West, FL Vacation Rental
- - - - - - - - - - - - - - - - -
The Ocean is Calling  - Marathon, FL Vacation Rental

The Ocean is Calling

Marathon, FL
5 Bed 3 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
390 - - - - - - - - - - - - 495 520 520 520
Turtle Key Complex - Islamorada, FL Vacation Rental

Turtle Key Complex

Islamorada, FL
6 Bed 6 Bath Sleeps 22 (20 Adults Max)
- - - - - - - - - - - - - - - - 1285
Ocean Oasis - Islamorada, FL Vacation Rental

Ocean Oasis

Islamorada, FL
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - 560 590 520 520 520
Leatherback Cottage - Upper Unit - Islamorada, FL Vacation Rental
- - - - - - - - - - - - - - - - 280
Breezy Palms & Tropical Charm - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Kemp's Cottage - Islamorada, FL Vacation Rental

Kemp's Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - 265
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- 170 180 170 - - - 180 195 195 190 - - - - - -
Sweet Serenity - Key Largo, FL Vacation Rental

Sweet Serenity

Key Largo, FL
3 Bed 2 Bath Sleeps 8
65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
- - - - - - - 170 180 180 180 180 220 220 180 180 180
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
215 225 225 225 225 195 - - - - - - 225 240 240 240 240
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Hawksbill Cottage - Islamorada, FL Vacation Rental

Hawksbill Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 3 (2 Adults Max)
- - - - - - - - - - - - - - - - 265
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - 455 470 470 470
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - 99 115 99 - - - - - - - 99 120 120 115
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - 150 - - - - - - - 165 195 195 195
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
- - - 195 220 185 - - - - - - - 190 - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
145 155 155 155 155 155 155 160 160 160 160 160 160 160 160 160 160
Green Turtle Cottage - Islamorada, FL Vacation Rental

Green Turtle Cottage

Islamorada, FL
2 Bed 1 Bath Sleeps 6 (4 Adults Max)
- - - - - - - - - - - - - - - - 250
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
145 145 145 145 145 145 145 145 - - - - - - - 145 155
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- 140 140 140 140 140 140 150 140 - - - - - - - 140
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - 155 160 160 140 - - - - - - - - - - -
Tropical Charm - Key Colony Beach, FL Vacation Rental

Tropical Charm

Key Colony Beach, FL
3 Bed 3.5 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
99 99 99 99 99 99 99 99 99 99 99 99 99 99 99 99 99
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - 165 195 195 195 195 190 - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
85 90 90 90 90 90 90 99 99 99 99 99 99 99 99 99 99
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
130 130 125 - - - - - - - - - - - 145 155 155
Landings of Largo Gem - Key Largo, FL Vacation Rental

Landings of Largo Gem

Key Largo, FL
2 Bed 2 Bath Sleeps 7 (4 Adults Max)
65 65 65 65 65 70 70 65 65 65 65 65 70 70 65 65 65
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
165 160 160 160 160 160 155 - - - - - - - - 160 170
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
130 130 130 130 130 99 - - - - - - - 115 135 135 135
Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - 240 250 250 250 250 265 265 265 265 265 265 265 265 250 -
White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- - - - 135 145 145 155 155 155 155 155 155 155 155 155 155
Eleventh Street Legacy - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - 145 155 155 145 - -
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- 145 145 145 145 145 145 155 155 155 155 155 155 155 155 155 155
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
- - - - - - - 99 99 99 99 99 99 99 99 99 99
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About Key West

Key West rated 4.9 out of 5 based on 44 reviews Key west, FL

For an island that is only two miles long and four miles wide, you'd think it would be a quiet place, demanding long trips outside the immediate area to reach attractions, good food, and historical sites. However, that's far from the case when you book one of our Key West vacation rentals! With a vibrant arts culture, a variety of opportunities for outdoor adventures, and a welcoming small-town attitude, Key West promises a unique and memorable vacation. 

When you book a stay in one of our Florida vacation rentals in Key West, you're not just booking a vacation; you're booking an experience!

Where is Key West, Florida? 

Our Key West vacation rentals are on the last island of the Florida Keys chain, about 160 miles from Miami and 98 miles from Key Largo. Whether you chose to arrive to this interesting island via plane, ferry, or car, the first sight of the expansive Atlantic Ocean promises to take your breath away. With its vibrant wildlife, you may even be lucky enough to spot a few dolphins splashing around and welcoming you to Key West!

Things to Do in Key West, Florida

Although the island is relatively small, the number of attractions are vast and varied! Key West has a diverse arts and history culture, including plenty of galleries, delicious restaurants, and landmarks that are as unique as the Keys themselves. The Hemingway Home, located in Old Key West, is a historical treat for guests who enjoy literature (and six-toed cats). With look-out towers and detailed exhibits of the wrecking business, the Shipwreck Museum is definitely worth a visit.

Other points of interest on the island include the Southernmost Point, and Wyland's Whaling Wall, a gorgeous mural of some of Key West's local aquatic residents. Key West has a laid-back attitude, but its night life isn't lacking! Let loose on Duval Street, starting in Mallory Square with its famous Sunset Celebration and working your way down the main drag to the (in)famous Sloppy Joe's. 

Feeling hungry after a long day full of excitement and adventure? Our Key West lodging is conveniently close to many dining options, including restaurants like Help Yourself, an organic cafe and juice bar, and Square One, a fine-dining establishment. 

Outdoor Activities in Key West, Florida

With so many diverse outdoor activities near our Key West vacation rentals, it might be difficult to decide where to start. However, one thing is for sure - water is Key West's playground! Book a charter with Sunset Sail Key West and admire the wildlife or catch one of those famous Florida sunsets. With early morning sunrise cruises, starlit float trips, snorkeling, and themes like "Cruise Concert" and "Wine and Wind" at dusk, there's something for everyone! 

While sandy beaches are not as common in the Keys due to the reef barrier, there are a few favorites that are worth a visit, including Smathers Beach, Ft. Zachary Taylor State Park, and the Dry Tortugas National Park, home to epic sandy beaches and historic Fort Jefferson. 

The natural beauty of Key West has been preserved thanks to the recent emphasis placed on ecotourism. With options for kayaking, scuba diving, or snorkeling, you'll be able to admire wildlife in its natural habitat while helping conservation efforts to maintain the Keys. View the reef up close with a trip on a glass-bottom boat, or try a dolphin-viewing charter!

A vacation destination that combines the modern conveniences and comforts of home with a growing environmental awareness (and a memorable nightlife scene!), this beautiful island offers a glimpse into all that Florida has to offer. Plan a visit to one of our Key West vacation rentals for a memorable trip full of relaxation, exploration, and unforgettable experiences. 

Photo credit: Fotoluminate LLC via Shutterstock

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