Discover a selection of 153 holiday rentals in Florida Keys, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 114 per night, and houses and villas are popular options for a stay in Florida Keys. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Florida Keys
Destination guide

Lively Florida Keys will entice you

Enjoy the live music and other features of Florida Keys. Renowned for its dolphin watching, seaside and bars, this city welcomes all visitors. There are plenty of places to find the perfect souvenir, including Duval Street, Dadeland Mall and Brickell City Centre. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Things to do

Activities and attractions in Florida Keys

Are you looking for attractions to visit during your stay? Travellers enjoy fun activities like jogging trails, dolphin viewing and fishing. Venture out of your holiday home and check out everything that makes Florida Keys a one-of-a-kind holiday spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Florida Keys Country Club (8.1 mi / 13 km)
  • Key West Visitors Center (14.4 mi / 23.1 km)
  • Blue Hole (14.9 mi / 24 km)
Natural features

Exploring the beaches and other natural features in Florida Keys

Travellers appreciate the breathtaking sunsets and beautiful ocean views, which is just a taste of what Florida Keys has to offer. Whether you're an active traveller or just want to take in the scenery, Florida Keys is a great place to get out in nature. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Vaca Key (7 mi / 11.2 km)
  • Sombrero Beach (8.9 mi / 14.3 km)
  • Sunset Park Beach (10.4 mi / 16.7 km)
  • Bahia Honda State Park (11.1 mi / 17.8 km)
  • Coco Plum Beach (11.3 mi / 18.2 km)
  • Curry Hammock State Park (12.1 mi / 19.4 km)
How to get there

How to get to and around Florida Keys

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 40.8 mi (65.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Marathon, FL (MTH-Florida Keys Marathon), which is 8.7 mi (14.1 km) away.

What are the top holiday rentals in Florida Keys?

From luxury condos to inexpensive cottages, Vrbo has properties to match all tastes and budgets. Pack your bags and check out these top holiday rentals in Florida Keys:

  • "Sombrero Beach Home On Canal With Private Dock And Heated Pool": If you're searching for a comfy living space in Marathon, this rental won't disappoint. It comes with 3 bedrooms and quality amenities including heating and cookware, dishware and utensils.
  • "Key West Oasis, Seperate Cottage": Located in Key West Historic District, this guest favourite has 2 bedrooms and plenty of handy amenities. Coffee and tea making facilities and heating are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Florida Keys holiday rental for you.

What are the best tiny house holiday rentals in Florida Keys?

For a unique kind of experience, book a tiny house rental in Florida Keys. We'll warn you though — after you've lived the tiny house life, the urge to downsize and move into one of these mini digs will be hard to resist!

  • Get ready for a simpler way of life at "Annapolis Waterfront "tiny House" In Garden Setting". Amenities at this tiny house in Epping Forest include a garden and a kitchen.
  • "Tiny Home On 26 Private Lake Front Acres" in Elberton is another superb option. A nearby waterfront and a garden will help make your time here extra comfortable.

What are the top-rated holiday rentals for weekend getaways in Florida Keys?

Walk out of work on Friday and forget about those spreadsheets and networking invites. Gear up for a few days of good old-fashioned R&R — with a side order of adventure — at one of these leading weekend getaways in Florida Keys:

  • "Kayak Boot Key Harbour, 75ft Canal Home" in Marathon is an excellent base if you love the great outdoors. Get out and see the area's nature hot spots, like Eco Pond and Coco Plum Beach, or fill your days with activities. Golf and cycling are among your options.
  • You'll be able to fit so much into your weekend away at "Wow Private Pool, Ocean Front". This property is located in Marathon and is surrounded by exceptional sights like Veterans Memorial Park & Beach and Anne's Beach. Snorkeling and water skiing are some cool experiences also on your doorstep.

Can I find studio apartments for rent in Florida Keys?

If you're looking for something with more personality than the usual hotel room, you'll love our studio apartments in Florida Keys. Whip up a dish in your kitchenette, read a book on the lounge and feel completely at home. Here are some of our comfiest studios:

  • "Waterfront Luxury Living Inside And Out" in Marathon crams lots of handy amenities into its single space, including cable/satellite TV services and towels.
  • With lots of character and promising more privacy than a large hotel, "Ocean Front 1/1, Amazing Ocean" is another tempting option. It's located in Tavernier and comes with a water park and beach sun loungers.

Can I find short term rentals in Florida Keys?

Ditch the lackluster hotel experience for the privacy and comfort of your own place. Even if you only have several days to get away, you'll find short-term rentals in Florida Keys that feel like a home away from home. Here's a sample of them:

  • Located near the heart of Marathon, "Kayak Boot Key Harbour, 75ft Canal Home" is well suited to a short-term stay. Use it as your base to check off famous attractions nearby, such as Sombrero Beach and Seven Mile Bridge.
  • Find out what Marathon has to offer from "Wow Private Pool, Ocean Front". If you go for this favourite property, The Turtle Hospital and Curry Hammock State Park are sights to put on your to-do list.

What are the best romantic weekend getaways in Florida Keys?

If you'd like to woo your special someone, then stay somewhere special! Organise a romantic weekend getaway in Florida Keys at one of these hideouts and let love bloom:

  • "Sombrero Beach Home On Canal With Private Dock And Heated Pool" in Marathon will convince you to plan more romantic weekends away. Nice touches here include a restaurant dining guide and air conditioning.
  • Another tempting option is "Key West Oasis, Seperate Cottage" in Key West Historic District. Enjoy perks here including beauty services and shopping facilities, as well as each other's company.

Are there mansions for rent in Florida Keys?

With privacy, space and that extra wow factor, mansions offer a taste of something unique. If you think the whole crew deserves a slice of the high life, whisk them away to one of these mansions for rent in Florida Keys:

  • Spend a few nights enjoying the finer things in life at "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" in Old Town Key West. A swimming pool and beauty services are just a few of the great amenities you can expect here.
  • With a swimming pool and beauty services among its wealth of highlights, "Mediterranean Mansion In Florida Keys" also promises to make your stay an unforgettable one. You'll find these palatial digs in Key Largo.

What are the best large group holiday rentals in Florida Keys?

If your idea of the perfect trip away is to bring along all your friends, you'll be needing a whole bunch of space. Luckily, there are many holiday rentals in Florida Keys that are suitable for large groups, starting with these sprawling pads:

  • "New Photos: Drive To Your Getaway": This popular rental is a terrific choice for larger groups staying in Key West Historic District. It has 5 bedrooms and many great amenities, including a beach view and a swimming pool.
  • "Spectacular Waterfront Estate": You'll get your crew's tick of approval at this Marathon option which comes with a swimming pool, a nearby waterfront and more. It has 6 bedrooms that will easily house everyone on your invitation list.

Are there large holiday rentals that sleep 30 or more in Florida Keys?

Organising a trip to Florida Keys with all your favourite people doesn't have to mean piling everyone into one room. If you're looking for someplace comfy where you and your guests can spread out and relax, one of these large holiday rentals might suit you perfectly:

  • "All Together Now @ Old Town Three Homes And Pools + Last Key Services": With 13 bedrooms accommodating up to 32 people, you'll have ample space at this sizable property in Downtown Key West. Useful amenities here include a swimming pool and a barbecue grill.
  • "Moosybärhütte, Gruppenunterkunft Für Bis Zu 31 Personen": Accommodating up to 31 guests and with excellent amenities including a swimming pool and a garden, this is another standout. It has 5 bedrooms and is located in Bahama Village.

What are the best houses for rent with a pool in Florida Keys?

Get ready to take your pick and dive right in. Here are a couple of sought-after house rentals in Florida Keys where memories are made at the pool:

  • Kids, aunts, uncles, parents — everyone will enjoy the pool at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Take the whole family on a holiday at this Stock Island rental home which also comes with a swimming pool and books.
  • "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" in Key West is another guest favourite. There's a whole lot to love about this property apart from its pool, such as a nearby laundromat and a microwave oven.