Summerland Key Holiday Rentals

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Our top choices for Summerland Key holiday rentals

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"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 NZ$1,700
includes taxes & fees
22 Feb - 23 Feb
Atlantic View Luxury Villa with Pool

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,554
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,173 reviews)
"Very a nice place clean nice location good price"
United States
Pawel
The price is NZ$419
includes taxes & fees
11 Mar - 12 Mar
Knight's Key Suites

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
The price is NZ$1,311
includes taxes & fees
2 Mar - 3 Mar
Ocean Front One Bedroom Residence

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (301 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
The price is NZ$3,652
includes taxes & fees
2 Mar - 3 Mar
Contra House Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (178 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$678
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina

Southern Palms by Brightwild Pool Parking

Southern Palms by Brightwild Pool Parking
2.0 star property
Old Town Key West
Southern Palms by Brightwild Pool Parking

Sky Suites Retreat by Brightwild 2 Stunning Condos

Sky Suites Retreat by Brightwild 2 Stunning Condos
2.0 star property
Old Town Key West
The price is NZ$5,492
includes taxes & fees
11 Mar - 12 Mar
Sky Suites Retreat by Brightwild 2 Stunning Condos

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 NZ$1,037
includes taxes & fees
4 Mar - 5 Mar
New Rose Petal Petite Suite - Pool Parking

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is NZ$5,213
includes taxes & fees
2 Mar - 3 Mar
Waterfront Luxury Home - Tidelands House

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 NZ$1,019
includes taxes & fees
2 Mar - 3 Mar
Resort View 1BR Suite With Direct Pool Access

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is NZ$5,338
includes taxes & fees
2 Mar - 3 Mar
The Fairhaven House at Solaire Lunara Bay

Poolside Paradise by Brightwild Heated Pool

Poolside Paradise by Brightwild Heated Pool
2.0 star property
Old Town Key West
Poolside Paradise by Brightwild Heated Pool

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 NZ$1,098
includes taxes & fees
2 Mar - 3 Mar
The Bartlum Luxury Studio In Prime Location

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
The price is NZ$4,839
includes taxes & fees
2 Mar - 3 Mar
New Waterfront Home - Sunray House

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is NZ$1,136
includes taxes & fees
2 Mar - 3 Mar
Mesa House Uno by Brightwild Perfect Location

Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is NZ$1,352
includes taxes & fees
22 Feb - 23 Feb
Tortuga Suite Sparkling Pool Hot Tub

Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is NZ$3,235
includes taxes & fees
2 Mar - 3 Mar
Commodore s Cove by Brightwild Epic Location

Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
2.0 star property
Raccoon Key
Parking Pool Dock - Shellstone House
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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Find out more about Summerland Key

Everything you need to know about Summerland Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Summerland Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Summerland Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Summerland Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Summerland Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Summerland Key holiday rentals we have selected for you start as low as NZ$678 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Summerland Key rentals

At Expedia, we put the best Summerland Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Summerland Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Summerland Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Summerland Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Secluded Ocean View & Pool Near Key West: This highly rated holiday home rental in Summerland Key is located near the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, 1 hot tub and table football so that you can immerse yourself in your holiday. Some other top choices in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West.

How many holiday rentals are there in Summerland Key?

Choose from 472 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Venture Out Keys and Upper Sugarloaf Key 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.