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

Florida Keys Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Florida Keys vacation rentals

Exterior

1. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (354 reviews)
"Fantastic place! It was super clean and looked just like the photos. We would stay here again!"
United States
Clara
$223 nightly
The price is $251
Sep 2 - Sep 3
Total with taxes and fees
Yacht Haven Marina
BBQ/picnic area

2. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (232 reviews)
"Cleanness relaxing location, nice views, good air conditioning"
United States
Hakan
$228 nightly
The price is $256
Sep 2 - Sep 3
Total with taxes and fees
Aqua Lodge Rentals At Coconut Cay
25-inch flat-screen TV with digital channels, TV

3. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (173 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$271 nightly
The price is $305
Sep 20 - Sep 21
Total with taxes and fees
Treasure Harbor
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

4. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (367 reviews)
"Love being on the water in the houseboat. The dark skies were nice for stargazing"
United States
Lisa
$225 nightly
The price is $253
Sep 7 - Sep 8
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Premium bedding, soundproofing, iron/ironing board, WiFi (free)

5. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,228 reviews)
"It was absolutely amazing.We'll definitely stay there again"
United States
Jessica
$90 nightly
The price is $99
Sep 3 - Sep 4
Total with taxes and fees
Knight's Key Suites
Outdoor pool, sun loungers

6. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,289 reviews)
"Great spot"
Canada
Justin
$165 nightly
The price is $185
Sep 2 - Sep 3
Total with taxes and fees
Skipjack Resort & Marina
Exterior

7. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (736 reviews)
"Good location"
United States
Orlando
$130 nightly
The price is $146
Sep 6 - Sep 7
Total with taxes and fees
Breezy Palms Resort
Exterior

8. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (998 reviews)
"A/c was amazing, clean and beautiful cabins."
Canada
Natasha
$95 nightly
The price is $107
Sep 2 - Sep 3
Total with taxes and fees
Tropical Cottages
Front of property

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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$238 nightly
The price is $268
Sep 2 - Sep 3
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Beach towels

10. 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, (451 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
$204 nightly
The price is $227
Sep 7 - Sep 8
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
Lobby

11. Anchorage Resort & Yacht Club

Anchorage Resort & Yacht Club
3.0 star property
Key Largo
8.8 out of 10, Excellent, (342 reviews)
"Great place "
United States
Jay
$210 nightly
The price is $236
Sep 2 - Sep 3
Total with taxes and fees
Anchorage Resort & Yacht Club
Outdoor pool, pool umbrellas, sun loungers

12. 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, (144 reviews)
"Amazing stay "
United States
Anthony
$164 nightly
The price is $185
Sep 3 - Sep 4
Total with taxes and fees
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Exterior

13. Florida Keys Getaway - Slps 4 - Ocean View

Florida Keys Getaway - Slps 4 - Ocean View
Tavernier
9.8 out of 10, Exceptional, (38 reviews)
"A comfortable little condo, conveniently located for exploring the Keys. There’s a nice pool and small beach area with a bar/restaurant that are well maintained."
United States
Stephen
$267 nightly
The price is $297
Sep 8 - Sep 9
Total with taxes and fees
Florida Keys Getaway - Slps 4 - Ocean View
Exterior detail

14. 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, (136 reviews)
"Great place to stay"
United States
walter l.
$255 nightly
The price is $283
Sep 2 - Sep 3
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Interior

15. Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!

Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Old Town Key West
9.0 out of 10, Wonderful, (199 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
Sept Special@119.lodging + With 5 night stay 5th night FREE lodging!
Exterior detail

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, (110 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
$255 nightly
The price is $283
Sep 2 - Sep 3
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Pool

17. Amazing Ocean view condo

Amazing Ocean view condo
Tavernier
9.6 out of 10, Exceptional, (52 reviews)
"Excellent accommodations. Unit was even nicer than it looked in pictures, everything was clean and in working order. Enjoyed our stay very much and would definitely stay here again!"
United States
Jerad E.
$313 nightly
The price is $347
Sep 2 - Sep 3
Total with taxes and fees
Amazing Ocean view condo
1 bedroom, WiFi (free), bed sheets

18. Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Old Town Key West
9.6 out of 10, Exceptional, (53 reviews)
"Great property. Walking Blocks away from the downtown action, yet far away to be quiet. Parking is very tough. If you don’t need to rent a car because you’re going to be hanging out in town the whole time, don’t bother. Uber and transportation are plentiful but again, the parking is very difficult to find free parking."
United States
Timothy
$358 nightly
The price is $397
Sep 13 - Sep 14
Total with taxes and fees
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Beach nearby

19. Paradise in Key Largo, FL

Paradise in Key Largo, FL
Key Largo
9.8 out of 10, Exceptional, (76 reviews)
"Convenient, affordable, pet friendly, "
United States
mark e.
$263 nightly
The price is $292
Sep 13 - Sep 14
Total with taxes and fees
Paradise in Key Largo, FL
Private beach, sun loungers, beach umbrellas, beach towels

20. Island Bay Resort

Island Bay Resort
2.5 star property
Tavernier
10.0 out of 10, Exceptional, (179 reviews)
"Very pleased with our stay"
United States
Vernon Micheal
$227 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Island Bay Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Florida Keys Hotel Reviews

Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"We really enjoyed our stay there. Staff was very nice and helpful."
charlotte 2-night trip
Posted 2 hours ago
Rock Reef Resort

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 $99 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.

Explore a world of travel with Expedia