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

Our top choices for Summerland Key vacation 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 ₩315,342
₩849,530 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 ₩701,368
₩1,322,688 total
includes taxes & fees
Oct 3 - Oct 4
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 ₩123,625
₩332,263 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩94,583
₩135,933 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩176,406
₩236,582 total
includes taxes & fees
Sep 29 - Sep 30
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 ₩140,274
₩389,724 total
includes taxes & fees
Sep 26 - Sep 27
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 ₩447,600
₩832,887 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩1,118,123
₩1,800,009 total
includes taxes & fees
Sep 30 - Oct 1
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 ₩1,358,776
₩1,803,373 total
includes taxes & fees
Sep 24 - Sep 25
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 ₩263,774
₩422,687 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩263,774
₩422,687 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩334,501
₩781,125 total
includes taxes & fees
Sep 24 - Sep 25
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 ₩300,607
₩742,994 total
includes taxes & fees
Oct 4 - Oct 5
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 ₩339,055
₩864,706 total
includes taxes & fees
Sep 29 - Sep 30
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
The price is ₩338,925
₩624,177 total
includes taxes & fees
Sep 25 - Sep 26
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 ₩267,364
₩428,440 total
includes taxes & fees
Sep 28 - Sep 29
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 ₩1,059,496
₩2,181,471 total
includes taxes & fees
Oct 7 - Oct 8
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 ₩1,059,496
₩2,181,471 total
includes taxes & fees
Sep 24 - Sep 25
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 ₩1,059,496
₩2,181,471 total
includes taxes & fees
Sep 28 - Sep 29
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 ₩285,279
₩658,315 total
includes taxes & fees
Sep 27 - Sep 28
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
"Had a great time over the weekend . Great vibe!"
Michel 1-night trip
Posted 17 hours ago
Looe Key Reef Resort

Find out more about Summerland Key

Search for Vacation rentals in Summerland Key on Expedia.co.uk! You can easily find your home rentals, villas, Vacation 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 481 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.