Search 105,200+ Vacation Rentals

Florida Keys Vacation Rentals & House Rentals - 256 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

256 Vacation rentals

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$245

Book

from $245 / night

(10)

1 / 16

Key Largo Villa

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$175

Excellent (10 reviews)

Book

from $175 / night

(10)

1 / 19

Conch Key Cottage

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$175

Excellent (10 reviews)

Book

from $175 / night

1 / 16

Marathon Shores House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Private garden

from $143 / night

(123)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

$200

Excellent (123 reviews)

Book

from $200 / night

(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

$358

Excellent (1 reviews)

Book

from $358 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$228

Excellent (5 reviews)

Book

from $228 / night

(44)

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$200

Very Good (44 reviews)

Book

from $200 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414

Very Good (48 reviews)

Book

from $414 / night

(16)

1 / 11

Conch Key Cottage

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

$150

Excellent (16 reviews)

Book

from $150 / night

1 / 24

Duck Key Villa

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $535 / night

(5)

1 / 13

Ramrod Key House

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$158

Very Good (5 reviews)

Inquire

from $158 / night

(11)

1 / 51

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$900

Excellent (11 reviews)

Book

from $900 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly

$186

Very Good (5 reviews)

Book

from $186 / night

1 / 24

Marathon Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $200 / night

(17)

1 / 15

Key Largo House

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$450

Very Good (17 reviews)

Book

from $450 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

$200

Excellent (17 reviews)

Inquire

from $200 / night

(52)

1 / 36

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$209

Excellent (52 reviews)

Book

from $209 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Very Good (7 reviews)

Book

from $250 / night

1 / 14

Key Largo House

  • 2
  • 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly

$300

Book

from $300 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

Book

from $295 / night

1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $340 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$730

Excellent (20 reviews)

Inquire

from $730 / night

(2)

1 / 18

Key West Condo

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$209

Excellent (2 reviews)

Book

from $209 / night

(39)

1 / 10

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$157

Very Good (39 reviews)

Inquire

from $157 / night

(27)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$300

Very Good (27 reviews)

Inquire

from $300 / night

(9)

1 / 12

Marathon Shores House

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$358

Very Good (9 reviews)

Inquire

from $358 / night

(4)

1 / 9

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$142

Excellent (4 reviews)

Inquire

from $142 / night

(2)

1 / 16

Tavernier Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$175

Excellent (2 reviews)

Book

from $175 / night

(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$457

Excellent (3 reviews)

Inquire

from $457 / night

(1)

1 / 23

Summerland Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$500

Very Good (1 reviews)

Book

from $500 / night

(6)

1 / 14

Islamorada House

  • 3
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$214

Excellent (6 reviews)

Book

from $214 / night

1 / 22

Marathon Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $172 / night

(15)

1 / 16

Islamorada Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200

Excellent (15 reviews)

Inquire

from $200 / night

(1)

1 / 15

Key Largo Condo

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$145

Excellent (1 reviews)

Inquire

from $145 / night

(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$394

Excellent (11 reviews)

Inquire

from $394 / night

(9)

1 / 14

Islamorada House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$420

Excellent (9 reviews)

Book

from $420 / night

1 / 24

Key Largo Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

$155

Book

from $155 / night

(2)

1 / 17

Key Largo Townhouse

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$250

Excellent (2 reviews)

Inquire

from $250 / night

(8)

1 / 25

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$221

Excellent (8 reviews)

Book

from $221 / night

About Florida Keys

While all the Florida Keys serve up a high dose of tropical leisure, each has its own personality and flavor. The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Enjoy Key Largo’s reputation as the dive capital of the world; Islamorada’s spectacular fishing; Marathon’s family friendly beaches; Big Pine Key and the Lower Keys' slowed pace and natural playground; and the unforgettable Key West, the Southernmost city in the continental U.S. and playground to Presidents, authors, and a number of bon vivants. And each has it's own unique offering of Florida Keys oceanfront vacation rentals to choose from. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price.

Things to Do

Decide what sorts of fun in the sun you enjoy best and there’s a Key for that. If sports fishing and boating interests you, spend some time on Islamorada and take a dip in the Gulf Stream. If you wonder what inspired one of America’s top writers, don’t miss Key West and the historic Hemingway House. While you’re there, check out the descendants of his famous six-toed cats. No matter which Key you choose, the water is a draw around all of them. The crystalline blue surrounding these islands makes a drive up Highway 1 a spectacular way to spend some time, particularly if you’re in a convertible.

​The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Islamorada, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.

Climate

The weather is warm for much of the year, but the balmy Caribbean breezes make it comfortable along the beaches even in summer. The highest temp ever recorded in the Keys was 97 F (36 C) back in 1880, but the summer average high is 89 F. Mosquitos like the Keys too, so keep this in mind on your visit. The highest potential for hurricanes in this part of Florida is from August 15-October 15 when waters are warmest, but it’s also a time of some of the most beautiful weather and one of the most affordable times to visit.

Shopping 

While there are shops on all the Keys, Key West provides the largest number of stores and boutiques. From literary memorabilia to craft beer, Key West offers some of the most memorable shopping of these tropical hot spots.

Events

The Keys offer a number of fishing tournaments throughout the year, not only for sport but to keep certain populations under control, especially the pervasive lion fish. Don’t miss the annual Hemingway look-alike contest in July or Key West’s annual Halloween celebration, Fantasy Fest. If you go, leave the kids at home.  

Nightlife

Nightlife or daylife, you’re on Island time here, and there’s always a party to be found, particularly in Key West. When people say “It’s 5:00 somewhere,” that somewhere is the Keys. Just ask Jimmy Buffet who is sometimes spotted in Key West, where he opened his first Margaritaville store in the mid-80s. Most of the hot bars are within walking distance on Duvall Street, making it a favorite of those looking for a party.  

Beaches and Parks

Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.

Local History

Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.

Fun With Kids

While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
The Keys are a delightful mix of Old Florida and the Caribbean. They offer the recognizable feel of the U.S. with the laid back approach of the islands. Best of all, you don’t need a passport for this tropical adventure when you stay in one of the many Key West vacation rentals.
Read More