Florida Keys vacation rentals

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Popular amenities for Florida Keys vacation rentals

Other great vacation rentals in Florida Keys

Guest favorite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Oct 15 – 22

G$120,742 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

Marathon one-level home on the Marina - with slip!

Jul 11 – 18

G$131,374 GYD per night
Guest favorite

Home in Marathon

4.91 out of 5 average rating, 158 reviews

Beachfront Villa - Florida Keys

Dec 10 – 17

G$84,676 GYD per night
Guest favorite

Home in Key Largo

4.98 out of 5 average rating, 118 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Oct 7 – 14

G$48,819 GYD per night
Superhost

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

Jun 1 – 8

G$60,227 GYD per night
Guest favorite

Home in Key Largo

4.96 out of 5 average rating, 134 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

Mar 30 – Apr 6

G$60,017 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Mar 22 – 29

G$130,700 GYD per night
Guest favorite

Home in Key Largo

5.0 out of 5 average rating, 47 reviews

The Paradise 2

Nov 30 – Dec 7

G$77,987 GYD per night

Florida Keys beach vacation rentals

Guest favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Oct 24 – 31

G$71,353 GYD per night
Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 132 reviews

ATLANTIS...Ocean Front Cottage Retreat!

Jan 4 – 11

G$126,291 GYD per night
Superhost

Condo in Key West

4.93 out of 5 average rating, 132 reviews

Beach Club Ocean Front 2BR Condo

Dec 7 – 14

G$194,714 GYD per night
Guest favorite

Tiny home in Key Largo

4.98 out of 5 average rating, 165 reviews

The Oasis in key largo with your own private beach

Jan 28 – Feb 4

G$58,977 GYD per night
Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 526 reviews

Old Town - Room Opens to Pool and Garden

Jun 23 – 30

G$76,233 GYD per night
Superhost

Houseboat in Key West

4.84 out of 5 average rating, 174 reviews

Happys Houseboat

Aug 4 – 11

G$79,802 GYD per night
Guest favorite

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Jan 27 – Feb 3

G$102,478 GYD per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

May 25 – Jun 1

G$40,283 GYD per night

Beach home rentals in Florida Keys

Guest favorite

Home in Marathon

4.98 out of 5 average rating, 84 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Oct 12 – 19

G$97,010 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 35 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

May 5 – 12

G$95,319 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 6 reviews

Ocean Dream

Jul 13 – 20

G$215,352 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 30 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Dec 4 – 11

G$114,956 GYD per night
Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 42 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Aug 18 – 25

G$143,422 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Oceanfront *PARADiSE* Amazing views, pool, dock

Feb 8 – 15

G$209,775 GYD per night
Superhost

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 45 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Jan 27 – Feb 3

G$228,907 GYD per night
Guest favorite

Home in Key Largo

4.88 out of 5 average rating, 8 reviews

Waterfront Key Largo Home - Tropical Paradise

Mar 14 – 21

G$122,708 GYD per night

Your guide to Florida Keys

All About The Florida Keys

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.


The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


Top things to do in Florida Keys

Duval Street

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Marathon

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.

Destinations to explore

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