Summerland Key Vacation Rentals

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Our top choices for Summerland Key vacation rentals

8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
$285 nightly
The price is $316
Jan 31 - Feb 1
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!
9.0 out of 10, Wonderful, (54 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
$402 nightly
The price is $447
Feb 2 - Feb 3
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (163 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$311 nightly
The price is $345
Feb 15 - Feb 16
Total with taxes and fees
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$426 nightly
The price is $474
Feb 6 - Feb 7
Total with taxes and fees
Waterfront Home
3.5 star property
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
$966 nightly
The price is $1,087
Feb 9 - Feb 10
Total with taxes and fees
Atlantic View Luxury Villa with Pool
9.4 out of 10, Exceptional, (102 reviews)
"Great location. "
United States
Davian k.
$492 nightly
The price is $548
Feb 4 - Feb 5
Total with taxes and fees
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
$337 nightly
The price is $375
Feb 8 - Feb 9
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
$532 nightly
The price is $591
Feb 3 - Feb 4
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
$543 nightly
The price is $604
Feb 2 - Feb 3
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
$452 nightly
The price is $502
Feb 4 - Feb 5
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
9.0 out of 10, Wonderful, (92 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
$434 nightly
The price is $482
Feb 1 - Feb 2
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
$726 nightly
The price is $817
Feb 1 - Feb 2
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
$276 nightly
The price is $297
Jan 30 - Jan 31
Total with taxes and fees
Endless Summer Hideaway - lot 181
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
$700 nightly
The price is $778
Feb 25 - Feb 26
Total with taxes and fees
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
$933 nightly
The price is $1,035
Feb 6 - Feb 7
Total with taxes and fees
Beautiful Cottage & Amenities in Gated Community
10.0 out of 10, Exceptional, (5 reviews)
"Our house was beautiful and right on the water! Great sunrises and beautiful views! Fully equipped with everything you need or want! This home is the best VRBO we have rented! Would love to come back!!"
United States
Loretta F.
$646 nightly
The price is $675
Feb 8 - Feb 9
Total with taxes and fees
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
8.8 out of 10, Excellent, (158 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
$533 nightly
The price is $592
Jan 29 - Jan 30
Total with taxes and fees
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
$608 nightly
The price is $676
Feb 16 - Feb 17
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key
10.0 out of 10, Exceptional, (9 reviews)
"The property was really nice and super clean! Easy access and quiet neighborhood."
United States
VANESSA T.
$667 nightly
The price is $741
Feb 10 - Feb 11
Total with taxes and fees
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Vacation Home in Sugarloaf Key

Private and Exclusive Beach Getaway
8.0 out of 10, Very Good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
$2,581 nightly
The price is $2,845
Feb 23 - Feb 24
Total with taxes and fees
Private and Exclusive Beach Getaway
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 $316 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?

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West: This Summerland Key vacation home rental is located by the ocean and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Summerland Key are Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security and Old Florida Style, wrap around porch, boat basin for dockage, open water.

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 Sugarloaf Beach are a couple of lovely local spots to get outside and enjoy nature. Saddlebunch Keys and Venture Out Keys 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.