Summerland Key Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Summerland Key vacation rentals

Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 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
$975 nightly
The price is $1,097
Apr 12 - Apr 13
Total with taxes and fees
Atlantic View Luxury Villa with Pool
Outdoor dining

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (167 reviews)
"Great place "
United States
David
$346 nightly
The price is $383
Apr 22 - Apr 23
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Terrace/patio

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (179 reviews)
"Place was as advertised! We LOVE Venture out! There are park rules but if you follow them, you become family! Home was stocked and clean. Screened in back patio was a nice touch! Would stay in this unit again!"
United States
Thomas B.
$406 nightly
The price is $451
Apr 10 - Apr 11
Total with taxes and fees
Waterfront Home
Beach

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (197 reviews)
"Excellent location for staying in the Lower Keys. Sunrise view. Nice neighborhood setting. Close to real good places to eat, listen to music and chill. Would come back. "
United States
Ihor C.
$372 nightly
The price is $413
Apr 11 - Apr 12
Total with taxes and fees
Direct Oceanfront Cottage-Sunrise View- #2,
A heated pool

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very Good, (2 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
$578 nightly
The price is $634
Apr 12 - Apr 13
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
$450 nightly
The price is $499
Apr 19 - Apr 20
Total with taxes and fees
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Property grounds

Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
$299 nightly
The price is $323
Apr 10 - Apr 11
Total with taxes and fees
Endless Ocean Views - RV589
Exterior

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
$271 nightly
The price is $292
Apr 10 - Apr 11
Total with taxes and fees
Seabreeze Escape WF RV Lot 489
A heated pool

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
$529 nightly
The price is $581
Apr 11 - Apr 12
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
$450 nightly
The price is $499
Apr 13 - Apr 14
Total with taxes and fees
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (22 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.
$617 nightly
The price is $685
Apr 20 - Apr 21
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key
A heated pool

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
$612 nightly
The price is $672
Apr 10 - Apr 11
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Outdoor pool, a heated pool

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very Good, (16 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
$399 nightly
The price is $444
May 4 - May 5
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
$549 nightly
The price is $602
Apr 13 - Apr 14
Total with taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
$456 nightly
The price is $506
May 3 - May 4
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
Outdoor dining

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
$278 nightly
The price is $299
Apr 30 - May 1
Total with taxes and fees
Endless Summer Hideaway - lot 181
Exterior

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (96 reviews)
"We had a great time and will be back. "
United States
Michelle K.
$697 nightly
The price is $773
Apr 21 - Apr 22
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A heated pool

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$590 nightly
The price is $648
Apr 15 - Apr 16
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key
Outdoor pool

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (68 reviews)
"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "
United States
Paula D.
$1,169 nightly
The price is $1,297
Apr 22 - Apr 23
Total with taxes and fees
One of the very few beach houses with a daily, rental license in the Keys.
Pool

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
$1,709 nightly
The price is $1,893
Apr 21 - Apr 22
Total with taxes and fees
The Lighthouse - Beach Houses Key West
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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Fantastic place! We stayed in the hotel part of the resort - our apartment was big (even though it was the standard size) and it was spotless. The kitchen had all the plates, cups, and utensils etc you could need, and there was a washer and dryer with detergent. We loved the many USB ports all over the apartment to charge phones etc. Bathroom had a fantastic shower and was also spotless. The only minor issue we had was that there isn't a lot of hanging space for longer clothes. If you have any longer dresses, I'd recommend bringing your own coat hangers and use the hooks rather than the rail, but as I said.. minor issue. The staff are lovely, the pool is nice, the pub was popular (cooled with fans which was great) and the food was good. We will happily book this again next time we're in the keys!"
Elaine 5-night trip
Posted 19 hours ago
Sugarloaf Key Hotel at KOA Resort

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 $292 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.

Explore a world of travel with Expedia

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?

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West: This Summerland Key vacation home rental is located by the ocean and has an outdoor pool, a balcony, 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 an oven, so you can cook with friends or family. Some other top choices in Summerland Key are Private Secluded Ocean View & Pool Near 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 466 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

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