A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Florida Keys Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Florida Keys vacation rentals

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

1. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (785 reviews)
"Such a great place to stay!!"
United States
Gavin
$148 nightly
The price is $167
Nov 15 - Nov 16
Total with taxes and fees
Breezy Palms Resort
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

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,247 reviews)
"We had the pool view..Excellent!"
United States
Brandy
$107 nightly
The price is $118
Nov 29 - Nov 30
Total with taxes and fees
Knight's Key Suites
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (381 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
$201 nightly
The price is $226
Dec 4 - Dec 5
Total with taxes and fees
Old Wooden Bridge Resort and Marina
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

4. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,014 reviews)
"The family running the food truck and tiki hut were great. Felt like we were guests in their home."
United States
Douglas
$99 nightly
The price is $111
Nov 12 - Nov 13
Total with taxes and fees
Tropical Cottages
A beach with palm trees, a sandy path, and beach chairs.

5. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (239 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
$237 nightly
The price is $267
Nov 15 - Nov 16
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay
A marina with several docked boats and a row of small, white cabins with blue roofs.

6. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (384 reviews)
"Loved staying in the aqua lodges, such a relaxing place."
United States
Lauren
$255 nightly
The price is $287
Dec 1 - Dec 2
Total with taxes and fees
Yacht Haven Marina
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

7. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,298 reviews)
"Nice place"
United States
Gilbert
$205 nightly
The price is $231
Nov 15 - Nov 16
Total with taxes and fees
Skipjack Resort & Marina
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

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (353 reviews)
"Very clean Nice staff"
United States
Doris
$159 nightly
The price is $179
Nov 11 - Nov 12
Total with taxes and fees
Anchorage Resort & Yacht Club
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

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$257 nightly
The price is $289
Nov 11 - Nov 12
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

10. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (183 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
$234 nightly
The price is $263
Nov 11 - Nov 12
Total with taxes and fees
Treasure Harbor
A resort with a swimming pool, lounge chairs, and a view of the ocean.

11. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
$205 nightly
The price is $230
Nov 19 - Nov 20
Total with taxes and fees
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Exterior

12. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (61 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
$268 nightly
The price is $302
Nov 15 - Nov 16
Total with taxes and fees
Aqua Lodges at 47th Street Gulfside
A beachfront hotel with two palm trees, a flag, and a pool area with lounge chairs.

13. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (43 reviews)
"great stay and value! glad we went with this place for our trip, everyone loved it! beautiful, clean and the pool was great too!"
Canada
Nick
$307 nightly
The price is $341
Nov 16 - Nov 17
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Property grounds

14. Piece of Paradise

Piece of Paradise
2.0 star property
Key largo
$355 nightly
The price is $377
Dec 1 - Dec 2
Total with taxes and fees
Piece of Paradise
A wooden signpost with city names and distances in miles.

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

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (463 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$246 nightly
The price is $273
Dec 2 - Dec 3
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
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!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (115 reviews)
"Absolutely perfect! Great location, great property and great unit. Beautiful pool area with ice machine and filtered water dispenser was a highlight for the very hot and humid time we visited. Would return immediately and stay in the same spot. Thank you for a very enjoyable time in Key West!"
United States
Justin D.
$336 nightly
The price is $373
Dec 1 - Dec 2
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A wooden deck with a large tree, outdoor seating, and a marina in the background.

17. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (38 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
$282 nightly
The price is $315
Dec 1 - Dec 2
Total with taxes and fees
Poolside Cottage #412
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

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval
Old Town Key West
9.8 out of 10, Exceptional, (54 reviews)
"Great location, comfortable bed, and amazing communication."
United States
Ruben A.
$367 nightly
The price is $409
Nov 17 - Nov 18
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval
A tropical garden pathway leading to a building with a yellow facade and green shutters.

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

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
$321 nightly
The price is $356
Nov 11 - Nov 12
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A small, private entrance to a house with a brick pathway leading to a door.

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

Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Old Town Key West
10.0 out of 10, Exceptional, (41 reviews)
"Ricky’s Retreat is in a fantastic location. The room was all you need in Key West. Highly recommend it and will definitely stay there again."
United States
Brian R.
$343 nightly
The price is $382
Nov 16 - Nov 17
Total with taxes and fees
Ricky's Retreat - Truman @ Duval | Ideal Getaway!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Florida Keys Hotel Reviews

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

10/10 Excellent
"Very clean for Florida keys room - no complaints easy check in and out"
Anthony 3-night trip
Posted 11 hours ago
Old Wooden Bridge Resort and Marina

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Florida Keys in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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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