Summerland Key Vacation Rentals

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Our top choices for Summerland Key vacation rentals

8.2 out of 10, Very Good, (54 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
$361 nightly
The price is $400
Jan 20 - Jan 21
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
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
$881 nightly
The price is $991
Jan 16 - Jan 17
Total with taxes and fees
Atlantic View Luxury Villa with Pool
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
$619 nightly
The price is $687
Jan 27 - Jan 28
Total with taxes and fees
Beautiful Cottage & Amenities in Gated Community
2.0 star property
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.
$655 nightly
The price is $684
Jan 28 - Jan 29
Total with taxes and fees
135 Waterfront Property, Boat Dock, Heated Pool, Ocean Views
9.0 out of 10, Wonderful, (147 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$398 nightly
The price is $442
Jan 19 - Jan 20
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!

Cottage in Cudjoe Key

Waterfront Home
8.6 out of 10, Excellent, (175 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$358 nightly
The price is $397
Jan 19 - Jan 20
Total with taxes and fees
Waterfront Home
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
$700 nightly
The price is $778
Jan 18 - Jan 19
Total with taxes and fees
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
8.6 out of 10, Excellent, (155 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.
$286 nightly
The price is $317
Jan 21 - Jan 22
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!
2.5 star property
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
$545 nightly
The price is $604
Jan 19 - Jan 20
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
9.0 out of 10, Wonderful, (89 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.
$471 nightly
The price is $524
Feb 1 - Feb 2
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
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.
$674 nightly
The price is $748
Jan 21 - Jan 22
Total with taxes and fees
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
8.8 out of 10, Excellent, (65 reviews)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
$1,083 nightly
The price is $1,202
Jan 25 - Jan 26
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful "
United States
Lisa P.
$920 nightly
The price is $1,021
Jan 26 - Jan 27
Total with taxes and fees
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
10.0 out of 10, Exceptional, (12 reviews)
"outstanding views and house is spotless!"
United States
Virginia L.
$795 nightly
The price is $882
Jan 20 - Jan 21
Total with taxes and fees
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Vacation Home in Cudjoe Key

Southern Exposure in Cudjoe Key #49
2.0 star property
7.6 out of 10, Good, (4 reviews)
"The house is nice and sitting on the balcony feels like you're floating. It was a nice place to stay"
United States
Colleen G.
$651 nightly
The price is $681
Feb 8 - Feb 9
Total with taxes and fees
Southern Exposure in Cudjoe Key #49
9.4 out of 10, Exceptional, (101 reviews)
"Great location. "
United States
Davian k.
$561 nightly
The price is $623
Jan 22 - Jan 23
Total with taxes and fees
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
$676 nightly
The price is $760
Jan 28 - Jan 29
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
9.6 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "
United States
Lindsay C.
$670 nightly
The price is $744
Feb 5 - Feb 6
Total with taxes and fees
Reel Island Retreat #273 at Venture Out in the Florida Keys
8.6 out of 10, Excellent, (90 reviews)
"We had a great time and will be back. "
United States
Michelle K.
$734 nightly
The price is $815
Feb 4 - Feb 5
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
$700 nightly
The price is $778
Jan 17 - Jan 18
Total with taxes and fees
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
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.