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

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 P14,536
P39,161 total
includes taxes & fees
Sep 30 - Oct 1
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 P32,331
P60,972 total
includes taxes & fees
Oct 3 - Oct 4
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 P4,301
P6,182 total
includes taxes & fees
Sep 30 - Oct 1
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 P13,877
P21,024 total
includes taxes & fees
Sep 30 - Oct 1
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 P7,253
P16,946 total
includes taxes & fees
Sep 30 - Oct 1
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
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 P5,567
P16,923 total
includes taxes & fees
Sep 30 - Oct 1
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 P8,132
P10,906 total
includes taxes & fees
Sep 30 - Oct 1
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 P44,219
P74,764 total
includes taxes & fees
Oct 11 - Oct 12
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 P11,344
P18,567 total
includes taxes & fees
Sep 30 - Oct 1
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 P24,997
P50,100 total
includes taxes & fees
Oct 12 - Oct 13
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 P13,789
P21,318 total
includes taxes & fees
Oct 7 - Oct 8
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 P20,480
P47,394 total
includes taxes & fees
Sep 30 - Oct 1
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 P44,153
P72,479 total
includes taxes & fees
Oct 12 - Oct 13
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 P19,789
P43,019 total
includes taxes & fees
Oct 1 - Oct 2
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 P17,545
P32,882 total
includes taxes & fees
Sep 30 - Oct 1
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 P24,575
P27,647 total
includes taxes & fees
Oct 12 - Oct 13
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 P34,545
P62,526 total
includes taxes & fees
Oct 13 - Oct 14
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 P20,633
P38,393 total
includes taxes & fees
Sep 30 - Oct 1
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 P121,453
P194,690 total
includes taxes & fees
Oct 12 - Oct 13
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.
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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 3 hours ago
Sugarloaf Key Hotel at KOA 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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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.

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.