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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 Rp5.393.065
Rp12.269.548 total
includes taxes & fees
15 Oct - 16 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 Rp9.263.250
Rp17.469.281 total
includes taxes & fees
15 Oct - 16 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, (374 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 Rp1.594.890
Rp4.311.439 total
includes taxes & fees
15 Oct - 16 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, (1,239 reviews)
"Clean, easy check in and check out, nice supplies in the kitchen"
United States
Mengqiao
The price is Rp1.501.826
Rp2.074.684 total
includes taxes & fees
19 Oct - 20 Oct
Knight's Key Suites
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the 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 Rp1.917.090
Rp5.221.917 total
includes taxes & fees
15 Oct - 16 Oct
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

6. 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 Rp5.809.023
Rp10.884.850 total
includes taxes & fees
19 Oct - 20 Oct
Grand Marina Suite by Brightwild Waterfront
A balcony with a view of the sea, a chair, and a building with a green wall.

7. 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 Rp3.044.790
Rp3.928.915 total
includes taxes & fees
15 Oct - 16 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A modern house with a swimming pool, a balcony, and a well-maintained garden.

8. 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 Rp12.655.300
Rp21.397.212 total
includes taxes & fees
19 Oct - 20 Oct
Contra House Key West
Exterior

9. 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 Rp3.882.273
Rp5.946.338 total
includes taxes & fees
27 Oct - 28 Oct
Island View 1BR Residence With Balcony
Room

10. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is Rp3.652.784
Rp5.688.162 total
includes taxes & fees
15 Oct - 16 Oct
Resort View 1BR Suite
A poolside area with lounge chairs, a wooden table, and palm trees.

11. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is Rp22.930.151
Rp43.839.619 total
includes taxes & fees
18 Oct - 19 Oct
The Fairhaven House at Solaire Lunara Bay
A white two-story house with a balcony and a swimming pool.

12. 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 Rp13.750.446
Rp27.873.952 total
includes taxes & fees
15 Oct - 16 Oct
Capmar House by Brightwild Huge Home Pool
A white two-story house with a central archway and a paved driveway.

13. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is Rp18.340.229
Rp37.548.258 total
includes taxes & fees
26 Oct - 27 Oct
Palmgale House in Key West
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

14. Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp27.873.952 total
includes taxes & fees
25 Oct - 26 Oct
Aquaria House by Brightwild Pool Boat Dock
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

15. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp27.873.952 total
includes taxes & fees
18 Oct - 19 Oct
Mastway House by Brightwild Pool Dock
A two-story house with a swimming pool, surrounded by greenery and palm trees.

16. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp27.873.952 total
includes taxes & fees
19 Oct - 20 Oct
Seagate House by Brightwild Waterfront w Dock
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

17. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp27.873.952 total
includes taxes & fees
18 Oct - 19 Oct
Evershore House Pool Parking Dock
A modern kitchen with a central island, bar stools, and a large window.

18. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
3.0 star property
Raccoon Key
The price is Rp18.757.052
Rp38.017.184 total
includes taxes & fees
15 Oct - 16 Oct
Brand New Catchlight House With Private Pool
A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

19. Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp30.918.742 total
includes taxes & fees
19 Oct - 20 Oct
Suncoast House by Brightwild Pool Boat Dock
A living room with two sofas, a coffee table, and a view of the outdoors.

20. Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is Rp13.750.446
Rp27.873.952 total
includes taxes & fees
18 Oct - 19 Oct
Waterlane House by Brightwild Pool Boat 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

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 16 hours ago
Sugar Loaf Lodge

Find out more about Summerland Key

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

  • View our selection of featured holiday rentals in Summerland Key
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  • Enter your travel dates to view the best deals on holiday rentals in Summerland Key while they last

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.