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

Summerland Key Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Summerland Key holiday rentals

A wooden deck with a swing chair overlooking a lush landscape.

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 HK$1,825
HK$4,916 total
includes taxes & fees
30 Sept - 1 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 HK$4,059
HK$7,654 total
includes taxes & fees
3 Oct - 4 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, (372 reviews)
"Nice place"
United States
abhimanyu
The price is HK$706
HK$1,897 total
includes taxes & fees
27 Sept - 28 Sept
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, (1,235 reviews)
"Clean room with exceptional hospitality"
United States
chantal
The price is HK$540
HK$776 total
includes taxes & fees
28 Sept - 29 Sept
Knight's Key Suites
A resort with a pool, lounge chairs, and a view of the ocean.

5. 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, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is HK$1,169
HK$1,535 total
includes taxes & fees
27 Sept - 28 Sept
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

6. 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
The price is HK$812
HK$2,255 total
includes taxes & fees
26 Sept - 27 Sept
Aqua Lodges at Hurricane Hole Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.

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 HK$2,590
HK$4,820 total
includes taxes & fees
26 Sept - 27 Sept
Grand Marina Suite by Brightwild Waterfront
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 HK$5,545
HK$9,375 total
includes taxes & fees
11 Oct - 12 Oct
Contra House Key West
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

9. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
The price is HK$7,757
HK$10,296 total
includes taxes & fees
26 Sept - 27 Sept
Coconut Mallory Marina and Resort Condo

10. 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 HK$1,526
HK$2,446 total
includes taxes & fees
27 Sept - 28 Sept
Island View 1BR Residence With Balcony

11. 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 HK$1,526
HK$2,446 total
includes taxes & fees
28 Sept - 29 Sept
Resort View 1BR Suite
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

12. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is HK$1,936
HK$4,520 total
includes taxes & fees
6 Oct - 7 Oct
The Grenada Suite Pool View Private Balcony
A modern kitchen with a large island, a built-in sink, and a dining area with a blue sofa and chairs.

13. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is HK$2,268
HK$4,894 total
includes taxes & fees
26 Sept - 27 Sept
Tortuga Suite Sparkling Pool Hot Tub
A wooden pathway leading to a beach with palm trees and a clear blue sky.

14. Island Time Gorgeous Condo Steps To The Beach

Island Time Gorgeous Condo Steps To The Beach
2.0 star property
Key West
The price is HK$1,970
HK$4,975 total
includes taxes & fees
30 Sept - 1 Oct
Island Time Gorgeous Condo Steps To The Beach
A porch with a white railing, a pink door, and a white fence.

15. New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
New Rose Petal Petite Suite - Pool Parking

16. Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is HK$1,526
HK$2,446 total
includes taxes & fees
28 Sept - 29 Sept
Resort View 1BR Suite With Direct Pool Access
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 HK$6,131
HK$12,623 total
includes taxes & fees
5 Oct - 6 Oct
Evershore House Pool Parking Dock
A white two-story house with a balcony and a swimming pool.

18. 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 HK$6,131
HK$12,623 total
includes taxes & fees
5 Oct - 6 Oct
Capmar House by Brightwild Huge Home Pool
A two-story house with a swimming pool, surrounded by greenery and palm trees.

19. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
2.0 star property
Raccoon Key
The price is HK$6,131
HK$12,623 total
includes taxes & fees
26 Oct - 27 Oct
Seagate House by Brightwild Waterfront w Dock
A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

20. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is HK$1,578
HK$3,701 total
includes taxes & fees
27 Sept - 28 Sept
The Bartlum Luxury Studio In Prime Location
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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"The lady that checked me in was super cool. Had"
Kevin 1-night trip
Posted 1 day ago
Looe Key Reef Resort

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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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. Another good choice for your trip to Summerland Key is Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball.

How many holiday rentals are there in Summerland Key?

Choose from 481 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.