A beach with a historic brick fort, a small seaplane, and a group of people walking along the shore.

Florida Keys Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Florida Keys vacation rentals

A beach with palm trees, thatched-roof huts, and lounge chairs.

1. Breezy Palms Resort

Matecumbe

Gavin

CA $189 total

includes taxes & fees

Nov 9 - Nov 10

A neatly made bed with a grey and white duvet, a wooden headboard, and a bedside table with a lamp and remote control.

2. Knight's Key Suites

Marathon

Brandy

CA $170 total

includes taxes & fees

Nov 29 - Nov 30

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Punta Brisa

Jordan

CA $310 total

includes taxes & fees

Dec 4 - Dec 5

An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

4. Tropical Cottages

Marathon

Douglas

CA $157 total

includes taxes & fees

Nov 10 - Nov 11

A beach with palm trees, a sandy path, and beach chairs.

5. Aqua Lodge Rentals At Coconut Cay

Marathon

Susan

CA $368 total

includes taxes & fees

Nov 15 - Nov 16

A marina with several docked boats and a row of small, white cabins with blue roofs.

6. Yacht Haven Marina

Marathon

Lauren

CA $385 total

includes taxes & fees

Dec 1 - Dec 2

A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

7. Skipjack Resort & Marina

Marathon

Justin

CA $310 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a large window, a white sofa, a coffee table, and a painting of a tropical scene.

8. Anchorage Resort & Yacht Club

Key Largo

Doris

CA $253 total

includes taxes & fees

Nov 9 - Nov 10

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

9. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

CA $405 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

10. Treasure Harbor

Islamorada

Diane

CA $355 total

includes taxes & fees

Nov 11 - Nov 12

A resort with a swimming pool, lounge chairs, and a view of the ocean.

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Arianna

CA $300 total

includes taxes & fees

Nov 18 - Nov 19

12. Aqua Lodges at 47th Street Gulfside

Marathon

Lauren

CA $399 total

includes taxes & fees

Nov 10 - Nov 11

A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

13. Florida Keys Getaway - Slps 4 - Ocean View

Tavernier

Nick

CA $512 total

includes taxes & fees

Nov 16 - Nov 17

14. Piece of Paradise

Key largo

CA $533 total

includes taxes & fees

Dec 2 - Dec 3

A wooden signpost with city names and distances in miles.

15. Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West

Laura D.

CA $367 total

includes taxes & fees

Dec 2 - Dec 3

A tropical garden pathway leading to a building with a yellow facade and green shutters.

16. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Old Town Key West

Justin D.

CA $522 total

includes taxes & fees

Dec 1 - Dec 2

A rectangular swimming pool with a metal ladder, surrounded by lounge chairs and umbrellas, with palm trees and a wooden fence in the background.

17. Poolside Cottage #412

Key West

shannon b.

CA $446 total

includes taxes & fees

Dec 1 - Dec 2

A courtyard with a gravel path, palm trees, and a building with a white facade.

18. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

Old Town Key West

Ruben A.

CA $552 total

includes taxes & fees

Nov 17 - Nov 18

19. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Old Town Key West

walter l.

CA $484 total

includes taxes & fees

Nov 10 - Nov 11

A small, private entrance to a house with a brick pathway leading to a door.

20. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Old Town Key West

Brian R.

CA $525 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Florida Keys Hotel Reviews

A beach with palm trees, a thatched-roof structure, and kayaks.

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

10/10 Excellent

Daniel

A beach with two thatched umbrellas, three sun loungers, and a view of the sea with boats.

Dolphin Point Villas

Key Largo

10/10 Excellent

Patricia

A wooden deck with white railings, outdoor seating, and a view of the sea with palm trees.

Coconut Palm Inn

Tavernier

10/10 Excellent

erika

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

The Perry Hotel & Marina Key West

Stock Island

10/10 Excellent

Lovely boutique hotel located in a marina. Very romantic spot. Really nice pool area and a good gym. Staff is very friendly. Restaurants were quite good as well The only reason I am not giving 5 stars is because there was a really funky smell in the rooms and halls that really bothered us. Not sure what it was. Also the beds were not comfortable and seemed “worn out”. They need to be replaced/upgraded.

Trisha

Lime Tree Bay Resort

Long Key

10/10 Excellent

Deborah

A beach with palm trees and lounge chairs.

Chesapeake Beach Resort

Matecumbe

10/10 Excellent

Alexandre

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

Islander Resort

Matecumbe

10/10 Excellent

This resort was absolutely amazing and exceeded all of my expectations. We originally booked just one night on our way to Key West, but after experiencing everything the property had to offer, we wished we had stayed much longer. If we have the opportunity to make this trip again, we would choose to stay here for our entire vacation and simply take a day trip or two to Key West. The resort offers everything you need for a relaxing and enjoyable stay, with beautiful surroundings, excellent...

Amanda

A beach with lounge chairs, palm trees, and a view of the water.

Atlantic Bay Resort

Tavernier

10/10 Excellent

Anonymous traveller

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Rifat

A hammock on a sandy beach with palm trees, a pool, and lounge chairs in the background.

Seascape Resort & Marina

Marathon

10/10 Excellent

Our trip was planned to go to Key West but didn't want to pay the higher prices there so we stayed in Marathon where this motel is located. We are very glad we did as it is a little gem tucked away. We would of like to of stayed longer as we found this motel had a very relaxing atmosphere not like the bigger places with the hustle and bustle. As mentioned below the only negative thing was the pool not heated leaving it very cold and the ocean beach is not really set up to swim in. Both my...

Karen & Rob

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Cheze

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

Silver Palms Inn & Historic Homes

Old Town Key West

10/10 Excellent

Kimberly

A wooden deck with a pool and chairs overlooking a beach with palm trees.

Grassy Flats Resort & Beach Club

Marathon

10/10 Excellent

KAREN

A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

Alexander Palms Court

Old Town Key West

10/10 Excellent

Steven was an absolute gem! When we checked out of the hotel, we asked Steven if it would be ok to leave our car at the hotel while we wandered around for a bit. Without hesitation he agreed. When we came back a couple of hours later, there was a sign next to my car saying that id forgotten my phone in the room. Thank you, thank you, thank you Steven! You just dont find people that go the extra mile anymore! Would absolutely stay here again!!

Shannon

Find out more about Florida Keys

Everything you need to know about Florida Keys vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Florida Keys vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Florida Keys vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Florida Keys vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Florida Keys. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Florida Keys vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Florida Keys vacation rentals we have selected for you start as low as CA $98 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Florida Keys rentals

At Expedia, we put the best Florida Keys vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Florida Keys rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Florida Keys vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Florida Keys. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Florida Keys Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Florida Keys vacation rentals

1. Breezy Palms Resort

2. Knight's Key Suites

3. Old Wooden Bridge Resort and Marina

4. Tropical Cottages

5. Aqua Lodge Rentals At Coconut Cay

6. Yacht Haven Marina

7. Skipjack Resort & Marina

8. Anchorage Resort & Yacht Club

9. Aqua Lodges at Hurricane Hole Marina

10. Treasure Harbor

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

12. Aqua Lodges at 47th Street Gulfside

13. Florida Keys Getaway - Slps 4 - Ocean View

14. Piece of Paradise

15. Steps from Duval, Pool on Site & Bikes Included!

16. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

17. Poolside Cottage #412

18. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

19. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

20. Ricky's Retreat - Truman @ Duval | Ideal Getaway!

Find vacation rentals that suit your style

Top Florida Keys Hotel Reviews

Kona Kai Resort and Gallery - Adults Only

10/10 Excellent

Find out more about Florida Keys

Florida Keys vacation rentals: An excellent choice for every season

How to find incredible deals on Florida Keys rentals

Explore a world of travel with Expedia