Florida Keys Vacation Rentals & House Rentals - 115 Rentals Available
115 Vacation rentals
Bayfront Vacation Home Villa Rental Bayside Beach View
Key Largo Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$230.00
from $230.00 / night
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 2 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 27 minutes
$297.00
from $297.00 / night
CARIBBEAN SOUL SAILING CHARTER Bayfront 2 BR cottage w/ 23 foot Sailboat or dock
Conch Key Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 12 mi
- Child friendly
$327.00
from $327.00 / night
Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*
Key Largo Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$258.00
from $258.00 / night
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Key West Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 16 16
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Swimming pool
$2,004.00
from $2,004.00 / night
Florida Keys Fishing & Diving, waterfront Home heated pool, deep dock, parking
Marathon House
- 4 bedrooms 4
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 2 mi
- Swimming pool
$974.00
from $974.00 / night
Florida Keys Beach Home Pool Fishing Diving
Marathon House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$287.00
from $287.00 / night
Bayfront Vacation Home Beach House Rental Bayside Steps from the Water
Key Largo House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 9 9
- 4 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$487.00
from $487.00 / night
Waterfront Get Hooked
Marathon House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$350.00
from $350.00 / night
Key Largo Rental Fantastic Views
Key Largo Condo
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 40 minutes
$344.00
from $344.00 / night
the private & secluded PENINSULARHOUSE/MANGROVE/TREEHOUSE off Grassy Key harbor.
Marathon Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$363.00
from $363.00 / night
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$1,300.00
from $1,300.00 / night
OCEANFRONT LUXURY "Mar Azul"
Marathon House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 15 minutes
$499.00
from $499.00 / night
Diving, Fishing, Snorkeling, Kayaking Paradise
Key Largo Townhouse
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 40 minutes
$401.00
from $401.00 / night
Best waterfront view in Marathon, pool, golf, dock
Marathon Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Child friendly
Responds fast! Avg. 3 hours 48 minutes
$153.00
from $153.00 / night
Ocean View Estate with Private Pool 15 minutes from Key West
Key West House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Nearest beach 10 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 37 minutes
$544.00
from $544.00 / 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
$1,472.00
from $1,472.00 / night
Key Largo Oceanfront Condo with Dock and Spectacular views
Key Largo Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 40 minutes
$401.00
from $401.00 / night
Penthouse Sunsets and Tropical Breeze in Key Largo
Key Largo Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 5 nights min
- Beach/lakeside relaxation
- Nearest beach 3 mi
- Swimming pool
$258.00
from $258.00 / night
Key Largo Ocean Front Villa with Dock and Incredible views
Key Largo Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.01 mi
- Swimming pool
Responds fast! Avg. 3 hours 40 minutes
$573.00
from $573.00 / night
Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock
Key Largo Townhouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.01 mi
- Swimming pool
Responds fast! Avg. 3 hours 40 minutes
$401.00
from $401.00 / night
Waterside Bay
Cudjoe Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 28 nights min
- Ask about children
- Air conditioning
- Ask about pets
$196.00
from $196.00 / night
ROCK HARBOR CLUB P-8
Key Largo House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Ask about children
$104.00
from $104.00 / night
TWICE THE CHARM
Key Largo House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 90 nights min
- Swimming pool
- Ask about children
- Pet friendly
$250.00
from $250.00 / night
Catch of the Day!
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$125.00
from $125.00 / night
BEACON REEF 310
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Swimming pool
- Ask about children
$124.00
from $124.00 / night
LITTLE BAY - Upper Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$429.00
from $429.00 / night
LYONS LANDING
Islamorada House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 30 nights min
- Swimming pool
- Ask about children
- Pet friendly
$292.00
from $292.00 / night
BROCK HAUS ON THE GULF
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
$228.00
from $228.00 / night
SUNSHINE PLACE
Islamorada Villa
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 7 nights min
- Ask about children
- Pet friendly
$210.00
from $210.00 / night
LITTLE BAY - Cottage
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
$429.00
from $429.00 / night
$266.00
from $266.00 / night
FLAMINGO COTTAGE
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Ask about children
- Pet friendly
$117.00
from $117.00 / night
LITTLE BAY - Lower Duplex
Islamorada Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Ask about children
- Pet friendly
$429.00
from $429.00 / night
BEACON REEF 222
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Swimming pool
- Ask about children
$134.00
from $134.00 / night
BEACON REEF 406
Matecumbe Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Swimming pool
- Ask about children
$120.00
from $120.00 / night
MY PARADISE
Layton House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Pet friendly
$275.00
from $275.00 / night
BEACON REEF 522
Matecumbe Key Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Swimming pool
- Ask about children
$155.00
from $155.00 / 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 Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.