Florida Keys Vacation Rentals & House Rentals - 256 Rentals Available
256 Vacation rentals
Life in Paradise w/ Slip at #1 Rated Coral Lagoon
Marathon Townhouse
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$245
from $245 / night
Tropical Retreat With Sandy Beach
Key Largo Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$175
from $175 / night
Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat
Conch Key Cottage
- 2 bedrooms 2
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$175
from $175 / night
M5 "Tropicana"
Marathon Shores House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
- Private garden
$143
from $143 / night
2 bedroom Condo Presented Key West Style
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Nearest beach 2 mi
- Swimming pool
- Child friendly
$200
from $200 / night
Brand New 4/3 Pool Home on Canal near lagoon
Marathon Shores House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Nearest beach 1 mi
- Swimming pool
- Child friendly
$358
from $358 / night
Beautiful, Oversize 2BR/King Beds w/ Large Outdoor Spaces, Location! Truman Annx
Key West Condo
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Nearest beach 0.5 mi
- Swimming pool
- Child friendly
$228
from $228 / night
Tropical Cottage with Sandy Beach
Key Largo Cottage
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$200
from $200 / night
Private & Peaceful Oceanview Estate Away From All
Cudjoe Key House
- 6 bedrooms 6
- 3 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$414
from $414 / night
Conch Key TreeTop one BR Cottage with 23' Sailboat
Conch Key Cottage
- 1 bedroom 1
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 12 mi
- Child friendly
$150
from $150 / night
Beautiful 3 Bedroom Duck Key Duplex
Duck Key Villa
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$535
from $535 / night
Oceanfront Home Rental in Ramrod Key, Florida
Ramrod Key House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$158
from $158 / night
Private Island Rental with 19' Boat, Seabird Key
Marathon House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$900
from $900 / night
Beautiful, End-Unit 2BR King/twins, Large, Private Deck. Location! Truman Annex
Key West Condo
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Nearest beach 0.5 mi
- Swimming pool
- Child friendly
$186
from $186 / night
Beautiful Tropical Retreat-Indigo Reef-3BR 2.5B
Marathon Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$200
from $200 / night
bayfront beach house with sandy beach
Key Largo House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- 4 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$450
from $450 / night
Best Old Town Location in Key West
Key West Townhouse
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Car not necessary
$200
from $200 / night
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$209
from $209 / night
Key West Condo 2 br, 2ba - ocean veiw from balcony
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$250
from $250 / night
The Main House
Key Largo House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 8 8
- 1 night min
- Child friendly
- Air conditioning
- Pet friendly
$300
from $300 / night
Penthouse Condo in Key West Florida
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$295
from $295 / night
Beautiful 2 Bedroom Duck Key Duplex
Duck Key Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$340
from $340 / night
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$730
from $730 / night
Ocean Front View Every Room*90' Scenic Balcony WIFI IN KEY WEST NOT ISLANDS AWAY
Key West Condo
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$209
from $209 / night
Kick back at Castaway
Marathon House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$157
from $157 / night
Key Largo Ocean Front Villa with Incredible views
Key Largo Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$300
from $300 / night
Florida Keys get-a-way in Marathon
Marathon Shores House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Child friendly
- Air conditioning
- Pet friendly
$358
from $358 / night
Deep Dockage "Fishing & Boating Dream"
Marathon House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$142
from $142 / night
Tarpon Cove at Ocean Pointe Resort
Tavernier Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$175
from $175 / night
Florida Keys Islamorada pool/home/canal Weekly
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
$457
from $457 / night
Water view Key West vacation from owner
Summerland Key House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$500
from $500 / night
Waterfront Paradise
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 10 10
- 30 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$214
from $214 / night
M79 Ocean Jewel
Marathon Condo
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$172
from $172 / night
Luxurious Waterfront with Two Masters, Pool, Hot Tub, Tennis, Gym, Dock, Bikes
Islamorada Condo
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$200
from $200 / night
Beautiful Moon Bay condo with view-Sunshine Vibe
Key Largo Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$145
from $145 / night
OCEANFRONT LUXURY "Mar Azul"
Marathon House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$394
from $394 / night
Islamorada Luxury Home Ocean & Bay Access
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$420
from $420 / night
Penthouse Sunsets and Tropical Breeze in Key Largo
Key Largo Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 3 mi
- Swimming pool
$155
from $155 / night
Diving, Fishing, Snorkeling, Kayaking Paradise
Key Largo Townhouse
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$250
from $250 / night
My Blue Heaven
Marathon House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$221
from $221 / night
About Florida Keys
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
- 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
- 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!
Fun With Kids
- 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.
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.