Summerland Key Vacation Rentals

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Our top choices for Summerland Key vacation 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
$881 nightly
The price is $991
Jan 16 - Jan 17
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$679 nightly
The price is $764
Jan 28 - Jan 29
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (172 reviews)
"Location , staff , and aqua lodge were perfect."
United States
William
$301 nightly
The price is $339
Jan 19 - Jan 20
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
$305 nightly
The price is $343
Jan 14 - Jan 15
Total with taxes and fees
Sunshine Key RV Resort & Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (286 reviews)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
$241 nightly
The price is $271
Jan 29 - Jan 30
Total with taxes and fees
Old Wooden Bridge Resort and Marina

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,164 reviews)
"Nice shower and great location room was clean and comfortable"
United States
Bruce
$162 nightly
The price is $179
Jan 14 - Jan 15
Total with taxes and fees
Knight's Key Suites

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$778 nightly
The price is $876
Jan 14 - Jan 15
Total with taxes and fees
Ocean Front One Bedroom Residence

Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
$1,277 nightly
The price is $1,436
Jan 16 - Jan 17
Total with taxes and fees
Coconut Mallory Marina and Resort Condo

Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
$1,535 nightly
The price is $1,726
Jan 14 - Jan 15
Total with taxes and fees
Contra House Key West

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
$1,499 nightly
The price is $1,687
Jan 25 - Jan 26
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool

Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
$610 nightly
The price is $687
Feb 4 - Feb 5
Total with taxes and fees
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
$603 nightly
The price is $679
Feb 8 - Feb 9
Total with taxes and fees
Tortuga Suite Sparkling Pool Hot Tub

The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
$736 nightly
The price is $829
Jan 25 - Jan 26
Total with taxes and fees
The Bartlum Luxury Studio In Prime Location

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
$794 nightly
The price is $893
Jan 19 - Jan 20
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
$754 nightly
The price is $848
Jan 14 - Jan 15
Total with taxes and fees
The Grenada Suite Pool View Private Balcony

Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
$566 nightly
The price is $636
Jan 14 - Jan 15
Total with taxes and fees
Banana Split by Brightwild Pool Grill

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
$981 nightly
The price is $1,104
Jan 14 - Jan 15
Total with taxes and fees
Duval Dream Loft by Brightwild Right on Duval

New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
$591 nightly
The price is $665
Feb 9 - Feb 10
Total with taxes and fees
New Rose Petal Petite Suite - Pool Parking

Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
$1,508 nightly
The price is $1,697
Jan 14 - Jan 15
Total with taxes and fees
Springtide House by Brightwild Waterfront Pool

Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
$811 nightly
The price is $912
Jan 14 - Jan 15
Total with taxes and fees
Sea Breeze by Brightwild Off-street Parking
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

Find out more about Summerland Key

Everything you need to know about Summerland Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Summerland Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Summerland Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Summerland Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $317 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Summerland Key rentals

At Expedia, we put the best Summerland Key vacation 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 vacation.

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 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?

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!: This Summerland Key vacation home rental is located on the waterfront and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Some other top choices in Summerland Key are Cudjoe Cottages, swimming pool, just 20 miles from Key West and Old Florida Style, wrap around porch, boat basin for dockage, open water.

How many vacation rentals are there in Summerland Key?

Choose from 485 Expedia vacation rentals in Summerland Key for a memorable vacation.

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 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.