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

Summerland Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 S$781
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 S$1,247
includes taxes & fees
3 Oct - 4 Oct
Atlantic View Luxury Villa with Pool
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

3. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,236 reviews)
"Clean room with exceptional hospitality"
United States
chantal
The price is S$126
includes taxes & fees
30 Sept - 1 Oct
Knight's Key Suites
A room with a bed, two armchairs, a small table, and a window with a view of palm trees and the sea.

4. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is S$427
includes taxes & fees
30 Sept - 1 Oct
Ocean Front One Bedroom Residence
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

5. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 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 S$346
includes taxes & fees
30 Sept - 1 Oct
Old Wooden Bridge Resort and Marina
A dining area with a wooden table and teal chairs, a sofa with blue cushions, and a painting of a beach scene.

6. 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 S$1,677
includes taxes & fees
30 Sept - 1 Oct
Coconut Mallory Marina and Resort Condo
A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

7. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is S$343
includes taxes & fees
30 Sept - 1 Oct
Aqua Lodges at Hurricane Hole Marina
A resort with a pool, lounge chairs, and a view of the ocean.

8. 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 S$223
includes taxes & fees
30 Sept - 1 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
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 S$1,527
includes taxes & fees
11 Oct - 12 Oct
Contra House Key West
Exterior

10. 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 S$347
includes taxes & fees
1 Oct - 2 Oct
Resort View 1BR Suite With Direct Pool Access
A bedroom with a bed, a ceiling fan, a painting, and a window.

11. Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is S$917
includes taxes & fees
1 Oct - 2 Oct
Sea Breeze by Brightwild Off-street Parking
Exterior

12. 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 S$337
includes taxes & fees
1 Oct - 2 Oct
Island View 1BR Residence With Balcony
Exterior

13. Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
The price is S$941
includes taxes & fees
1 Oct - 2 Oct
Resort View 3BR Residence
A spacious living room with a high ceiling, a dining area with a wooden table and blue chairs, and a cozy seating area with a sofa and armchairs.

14. Sky Suite on Duval by Brightwild Condo w Balcony

Sky Suite on Duval by Brightwild Condo w Balcony
2.0 star property
Old Town Key West
The price is S$1,387
includes taxes & fees
12 Oct - 13 Oct
Sky Suite on Duval by Brightwild Condo w Balcony
A pool area with a washing machine, chairs, and an umbrella.

15. Poolside Suite by Brightwild Pvt Pool Parking

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
Old Town Key West
The price is S$879
includes taxes & fees
11 Oct - 12 Oct
Poolside Suite by Brightwild Pvt Pool Parking
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

16. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is S$650
includes taxes & fees
28 Oct - 29 Oct
Resort View 2BR Residence
A beach view with palm trees, a wooden pier, and a sunset over the water.

17. Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
The price is S$415
includes taxes & fees
1 Oct - 2 Oct
Ocean Front 2BR Residence
A modern living room with a leather sofa, a dining table, and a staircase leading to another level.

18. The Collins on Duval by Brightwild

The Collins on Duval by Brightwild
2.0 star property
Old Town Key West
The price is S$1,223
includes taxes & fees
12 Oct - 13 Oct
The Collins on Duval by Brightwild
A beachside resort with a wooden deck, palm trees, and a sunset view.

19. 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 S$752
includes taxes & fees
30 Sept - 1 Oct
Grand Marina Suite by Brightwild Waterfront
A modern kitchen with a large island, wooden bar stools, pendant lighting, and a view of the outdoors.

20. NEW The Rigby House - Pvt Pool Amazing Location

NEW The Rigby House - Pvt Pool Amazing Location
2.5 star property
Key West Historic District
The price is S$3,779
includes taxes & fees
12 Oct - 13 Oct
NEW The Rigby House - Pvt Pool Amazing 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"I have nothing but nice things to say about the hotel, staff and property. You are welcomed with a happy and professional staff, and given first class service. The suites are pristine, well appointed and beautifully decorated with comfortable furnishings. You even get a washer and dryer in your unit. Parking is right under the units and there is a large elevator with luggage carts as well. The views are beautiful with a fantastic boat ramp for those with boats. Long story short, it is a must stay!"
Susan 4-night trip
Posted 13 hours ago
Sugarloaf Key Hotel at KOA Resort

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.