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 covered outdoor area with a wooden deck, palm trees, and a view of the beach.

1. Breezy Palms Resort

Matecumbe

Gavin

￥22,113 total

includes taxes & fees

Nov 17 - Nov 18

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

￥18,881 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

￥34,748 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

￥17,652 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living area with a gray sectional sofa, wooden beams, and a ceiling fan.

5. Aqua Lodge Rentals At Coconut Cay

Marathon

Susan

￥40,390 total

includes taxes & fees

Nov 15 - Nov 16

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

6. Yacht Haven Marina

Marathon

Lauren

￥42,520 total

includes taxes & fees

Dec 10 - Dec 11

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

￥34,801 total

includes taxes & fees

Nov 10 - Nov 11

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

￥28,349 total

includes taxes & fees

Nov 10 - Nov 11

A row of floating houses with balconies, connected by walkways, on calm water.

9. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

￥45,250 total

includes taxes & fees

Nov 10 - Nov 11

10. Treasure Harbor

Islamorada

Diane

￥41,382 total

includes taxes & fees

Nov 10 - Nov 11

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

￥36,494 total

includes taxes & fees

Nov 15 - Nov 16

12. Aqua Lodges at 47th Street Gulfside

Marathon

Lauren

￥43,718 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

￥57,167 total

includes taxes & fees

Nov 16 - Nov 17

14. Piece of Paradise

Key largo

￥59,806 total

includes taxes & fees

Dec 1 - Dec 2

A white building with a covered porch and a palm tree.

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

Old Town Key West

Laura D.

￥43,265 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.

￥58,540 total

includes taxes & fees

Dec 1 - Dec 2

A wooden deck with a large tree, outdoor seating, and a marina in the background.

17. Poolside Cottage #412

Key West

shannon b.

￥49,525 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.

￥61,920 total

includes taxes & fees

Nov 29 - Nov 30

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

Old Town Key West

walter l.

￥64,344 total

includes taxes & fees

Nov 22 - Nov 23

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.

￥58,887 total

includes taxes & fees

Nov 18 - Nov 19

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Find vacation rentals that suit your style

Top Florida Keys Hotel Reviews

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

A tropical resort with a clear pool, palm trees, and lounge chairs.

Kona Kai Resort and Gallery - Adults Only

Rock Harbor

10/10 Excellent

Audrey

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

Keith

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late! When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...

Val

A waterfront property with multiple buildings, a dock, and a small island with palm trees.

Dolphin Point Villas

Key Largo

10/10 Excellent

We stayed here on our way back from key west to lighten trip to FLL airport. We were in love with this place! Every thing about it, location, the high ceilings, the incredibly comfortable beds-the brand new smell of all dwellings. I also was in love with the toiletries that were provided!!! Never have I love a hotel toiletry before. All staff was very professional and friendly. The sunset on the pier was incredible, and our suite was overlooking the pool and it was amazing for a late night swim,...

Sherrie L.

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

Coconut Palm Inn

Tavernier

10/10 Excellent

A beautiful, hidden gem right on the water. They have kayaks and paddleboards to use with no cost. Complimentary breakfast, smores and wine. Everything was cleaned well. All the staff was friendly and helpful, especially Ashley. We were beyond impressed with the communication and helpfulness. We spoke to the gentleman who was renovating the rooms (even when he worked it was a quiet and peaceful place), and learned there will soon be a houseboat as a room to rent.

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

Janice

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

Lindsay

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Sonia

A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

Westwinds Inn

Key West Historic District

10/10 Excellent

The grounds of the property are absolutely beautiful. The gardens are well-maintained and we loved perusing them. Both pool areas are wonderful, and the amenities such as the bathhouse, lounge, library, and BBQ area are first rate. The room was to our liking and matched the aesthetic of Key West. Walking distance to nearby attractions was approximately 10 minutes and very easy, and the bakery just down the street was wonderful for breakfast, lunch, or a quick snack. We will absolutely stay again...

Daniel

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

Chesapeake Beach Resort

Matecumbe

10/10 Excellent

Paco

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

Islander Resort

Matecumbe

10/10 Excellent

Patrick

A poolside area with lounge chairs, umbrellas, and a pergola.

Ella's Cottages - Key West Historic Inns

Old Town Key West

10/10 Excellent

Cara

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

Atlantic Bay Resort

Tavernier

10/10 Excellent

Emily

Lime Tree Bay Resort

Long Key

10/10 Excellent

Jack

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

Grassy Flats Resort & Beach Club

Marathon

10/10 Excellent

We stayed at this hotel several times. It is very nice, It’s nice that they have a separate area for adults. They also have 3 in house places to eat, a tiki bar for lunch, a roof top for breakfast and bar in the evening and a restaurant for dinner (didn’t go to this one though). They include free paddle boards and kayaks. The rooms could have better A/C, they added another portable fan and seem to be having issues with A/C, hopefully will be resolved soon. Also they don’t have room service...

Victoria

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Vacation Apartments in Florida Keys

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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

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Find out more about Florida Keys

Vacation Apartments in Florida Keys