A coastal road with a beach on one side and a marina with boats on the other.

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Summerland Key holiday rentals

A wooden deck with a railing, wicker chairs, and a view of greenery.

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is ₹27,688
₹64,041 total
includes taxes & fees
27 Oct - 28 Oct
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

2. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is ₹48,888
₹92,196 total
includes taxes & fees
26 Oct - 27 Oct
Atlantic View Luxury Villa with Pool
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, (376 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is ₹8,458
₹22,864 total
includes taxes & fees
25 Oct - 26 Oct
Old Wooden Bridge Resort and Marina
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

4. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,242 reviews)
"We had the pool view..Excellent!"
United States
Brandy
The price is ₹7,287
₹10,239 total
includes taxes & fees
27 Oct - 28 Oct
Knight's Key Suites
A row of floating houses with balconies, connected by walkways, on calm water.

5. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (200 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ₹10,200
₹27,655 total
includes taxes & fees
31 Oct - 1 Nov
Aqua Lodges at Hurricane Hole Marina
A resort with a pool, lounge chairs, and a view of the ocean.

6. 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
The price is ₹17,001
₹21,797 total
includes taxes & fees
28 Oct - 29 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

7. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is ₹30,658
₹57,446 total
includes taxes & fees
25 Oct - 26 Oct
Grand Marina Suite by Brightwild Waterfront
A modern home with a glass door leading to a bedroom and a pool area.

8. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is ₹48,462
₹70,580 total
includes taxes & fees
9 Nov - 10 Nov
Lighthouse Suites Collection
A modern house with a swimming pool, a balcony, and a well-maintained garden.

9. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is ₹77,937
₹125,466 total
includes taxes & fees
27 Oct - 28 Oct
Contra House Key West
A white two-story house with a balcony and a swimming pool.

10. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is ₹72,921
₹147,820 total
includes taxes & fees
25 Oct - 26 Oct
Capmar House by Brightwild Huge Home Pool
Exterior

11. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is ₹20,489
₹31,382 total
includes taxes & fees
25 Oct - 26 Oct
Island View 1BR Residence With Balcony
Exterior

12. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
Two Bedroom Residence With Balcony
A poolside area with lounge chairs, a wooden table, and palm trees.

13. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is ₹121,602
₹232,488 total
includes taxes & fees
1 Nov - 2 Nov
The Fairhaven House at Solaire Lunara Bay
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

14. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is ₹72,569
₹147,107 total
includes taxes & fees
1 Nov - 2 Nov
Mastway House by Brightwild Pool Dock
A white two-story house with a central archway and a paved driveway.

15. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is ₹97,261
₹199,124 total
includes taxes & fees
25 Oct - 26 Oct
Palmgale House in Key West
A living room with two sofas, a coffee table, and a view of the outdoors.

16. Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is ₹72,921
₹147,820 total
includes taxes & fees
1 Nov - 2 Nov
Waterlane House by Brightwild Pool Boat Dock
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

17. Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is ₹72,921
₹147,820 total
includes taxes & fees
25 Oct - 26 Oct
Aquaria House by Brightwild Pool Boat Dock
A modern house with a swimming pool, outdoor seating, and palm trees.

18. Floralee House in Key West

Floralee House in Key West
2.0 star property
Raccoon Key
The price is ₹97,261
₹199,124 total
includes taxes & fees
27 Oct - 28 Oct
Floralee House in Key West
A modern kitchen with a central island, bar stools, and a large window.

19. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
3.0 star property
Raccoon Key
The price is ₹95,050
₹196,637 total
includes taxes & fees
27 Oct - 28 Oct
Brand New Catchlight House With Private Pool
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

20. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is ₹72,569
₹147,107 total
includes taxes & fees
5 Nov - 6 Nov
Evershore House Pool Parking Dock
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 Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Great"
Lori 7-night trip
Posted 1 hour ago
Sugarloaf Key RV Resort & Cottages

Find out more about Summerland Key

Holiday Rentals in Summerland Key

Search for holiday rentals in Summerland Key on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Summerland Key using one of the methods below:

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Look no further and take a look at our great range of rental properties in Summerland Key!

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Sugarloaf Key RV Resort & Cottages: This highly rated holiday home rental in Summerland Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Summerland Key?

Choose from 488 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Sound are other places to visit while you're in town.

What are holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.