Florida Keys Holiday Rentals – KAYAK

English

Search for a country or language

Recommended by KAYAK

Best Florida Keys holiday rentals

Villa of the Setting Sun - Summerland Key

Villa of the Setting Sun

Summerland Key, FL, United States

9.0Wonderful(25)

Pool

Air conditioning

Check availability

Atlantisocean Front Cottage Retreat - Summerland Key - Living room

Atlantisocean Front Cottage Retreat

Summerland Key, FL, United States

Free Wi-Fi

Pool

Air conditioning

Check availability

Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly. - Summerland Key - Dining room

Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.

Summerland Key, FL, United States

Air conditioning

Check availability

Oceanview Paradise At Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! - Summerland Key - Pool

Oceanview Paradise At Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Summerland Key, FL, United States

Pool

Air conditioning

Check availability

Kelly's Kabin - Adorable Private Summerland Key Cottage - Summerland Key - Patio

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key, FL, United States

Free Wi-Fi

Air conditioning

Check availability

Chic Ocean Miami 88 - Miami - Restaurant

Chic Ocean Miami 88

Miami, FL, United States

9.0Wonderful(40)

Parking

Free Wi-Fi

Air conditioning

Check availability

Sea Breeze Cottage - Venture Out Unit 066 - Summerland Key - Patio

Sea Breeze Cottage - Venture Out Unit 066

Summerland Key, FL, United States

Free Wi-Fi

Pool

Pet friendly

Air conditioning

Check availability

Tucker at Palmer Dadeland Miami - Miami - Bedroom

Tucker at Palmer Dadeland Miami

Miami, FL, United States

8.5Very Good(518)

Free Wi-Fi

Pool

Pet friendly

Air conditioning

Check availability

Nomada Residences - Miami - Balcony

Nomada Residences

Upper East Side

Air conditioning

Check availability

Colors On White - Key West - Bedroom

Colors On White

Old Town North of Truman

Parking

Free Wi-Fi

Pool

Pet friendly

Check availability

Ocean Breeze Cottage At Hidden Hammock - Summerland Key - Living room

Ocean Breeze Cottage At Hidden Hammock

Summerland Key, FL, United States

Free Wi-Fi

Air conditioning

Check availability

Beautiful And Comfortable Home and studios - Miami - Living room

Beautiful And Comfortable Home and studios

Flagami

9.5Wonderful(11)

Air conditioning

Check availability

Fabulous Studio 15 min from The Beach - Miami - Bedroom

Fabulous Studio 15 min from The Beach

Upper East Side

8.1Very Good(17)

Free Wi-Fi

Air conditioning

Check availability

One of the very few beach houses with a daily, rental license in the Keys. - Summerland Key

One of the very few beach houses with a daily, rental license in the Keys.

Summerland Key, FL, United States

Free Wi-Fi

Pool

Pet friendly

Air conditioning

Check availability

Waterfront Haven House with Boat Basin & Ramp - Summerland Key - Building

Waterfront Haven House with Boat Basin & Ramp

Summerland Key, FL, United States

9.8Wonderful(13)

Parking

Free Wi-Fi

Pet friendly

Air conditioning

Check availability

Sugarloaf Key Rv Resort & Cottages - Summerland Key

Sugarloaf Key Rv Resort & Cottages

Summerland Key, FL, United States

9.0Wonderful(153)

Parking

Free Wi-Fi

Pool

Pet friendly

Check availability

Search by review score

6+ Okay 7+ Good 8+ Great 9+ Excellent

Search by price

€0 - €500 €500 - €1,000 €1,000 - €1,501 €1,501 - €2,001 €2,001+ per night

Property type

Apartment Condo Cottage Homestay House

Search by freebies

Free cancellation Free breakfast Free parking Free internet

Useful Info

Low season	August
High season	December
Average price (weeknight)	€410
Average price (weekend night)	€292

Cheapest month to stay with an average 29% drop in price.

Most expensive month to stay with an average 82% rise in price.

Average Sun - Thu price over the last 2 weeks.

Average Fri & Sat price over the last 2 weeks.

Holiday rentals are a popular choice for both long and short-term stays. KAYAK users usually book their holiday rental in Florida Keys for 3 days.
Holiday rentals in Florida Keys are around 41% more expensive than hotels on average. Search here to compare prices for all accommodation types in Florida Keys.

How much is a holiday rental in Florida Keys for tonight?
In the last 72 hours, users have found Florida Keys holiday rentals for tonight for as little as €57. Search here for similar prices
What types of holiday rentals are available in Florida Keys?
There are loads of different property types that you can make your holiday home in Florida Keys. You’ll find boats, campgrounds, condos, houses, campsites, apartments, bungalows, cabins, caravans, cottages, lodges, motorhomes, houseboats, villas, towers, homestays, agritourism, chalets, luxury tents and caravan parks.
What are some of the most-loved holiday rentals available in Florida Keys?
There are many types of properties available for Florida Keys holiday rentals. If you’re looking for something special, holiday rentals most loved by KAYAK users are Tropical Cottages and Sun Outdoors Key Largo.
Are there any pet-friendly holiday rentals in Florida Keys?
There are a number of dog and pet-friendly Florida Keys holiday rentals, with around 16% allowing you to bring your pet along with you.

What Florida Keys holiday rental guests are talking about

Habitat Brickell by Sextant - Miami

Habitat Brickell by Sextant

Brickell

8.1Very Good(1436)

Free Wi-Fi

Pool

Air conditioning

Check availability

Hudson House - Miami

Miami, FL, United States

8.2Very Good(685)

Free Wi-Fi

Check availability

Four Ambassadors Apartments - Miami

Four Ambassadors Apartments

Brickell

Free Wi-Fi

Air conditioning

Check availability

Popular topics

Everything you need to know for your stay in Florida Keys

Complete your trip

Holiday rentals

Popular destinations

Complete your trip to Florida Keys

Flights to Florida Keys

Car hire in Florida Keys

Not what you’re looking for? Find thousands of other hotels, flights, car hires and package deals with KAYAK.