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

Summerland Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Summerland Key vacation 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 ￥47,706
￥108,533 total
includes taxes & fees
Oct 15 - Oct 16
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 ￥81,941
￥154,530 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥14,098
￥38,128 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥13,275
￥18,338 total
includes taxes & fees
Oct 19 - Oct 20
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)
"Poor outfitting of kitchen essentials."
United States
elmer j stewart
The price is ￥15,941
￥45,013 total
includes taxes & fees
Oct 15 - Oct 16
Aqua Lodges at Hurricane Hole Marina
A bedroom with a wooden bed, white bedding, a nightstand with a lamp, and two paintings on the wall.

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 ￥51,386
￥96,285 total
includes taxes & fees
Oct 15 - Oct 16
Grand Marina Suite by Brightwild Waterfront
A resort with a pool, lounge chairs, and a view of the ocean.

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 ￥28,359
￥36,358 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥111,946
￥189,276 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥34,342
￥52,601 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥32,312
￥50,317 total
includes taxes & fees
Oct 15 - Oct 16
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 ￥202,836
￥387,797 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 15 - Oct 16
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 ￥162,234
￥332,144 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥153,016
￥321,774 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥121,634
￥273,501 total
includes taxes & fees
Oct 19 - Oct 20
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 ￥121,634
￥246,567 total
includes taxes & fees
Oct 18 - Oct 19
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 15 hours ago
Sugar Loaf Lodge

Find out more about Summerland Key

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

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Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages: This Summerland Key vacation home rental 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 vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball.

How many vacation rentals are there in Summerland Key?

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

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 vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.