Holiday Rentals in Summerland Key

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Holiday Rentals in Summerland Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (73)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
The price is €291
includes taxes & fees
21 Nov - 22 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (99)
"The house was very clean. Friendly and quiet location. The hosts were extremely helpful. "
United States
Roy F.
The price is €360
includes taxes & fees
19 Nov - 20 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (158)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
The price is €281
includes taxes & fees
24 Nov - 25 Nov
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key
8.6 out of 10, Excellent, (150)
"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.
The price is €224
includes taxes & fees
15 Dec - 16 Dec
Cottage with Pool and Boat Dockage just minutes to Key West!

Endless Summer Hideaway - lot 181

Cudjoe Key
The price is €183
includes taxes & fees
14 Dec - 15 Dec
Endless Summer Hideaway - lot 181

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is €495
includes taxes & fees
3 Dec - 4 Dec
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €521
includes taxes & fees
19 Nov - 20 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
8.2 out of 10, Very good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is €279
includes taxes & fees
15 Dec - 16 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Cudjoe Key
10.0 out of 10, Exceptional, (7)
"Excellent place to stay on the water store right on premises will definitely be back have stayed 2 times this year "
United States
Anonymous traveller
The price is €545
includes taxes & fees
19 Nov - 20 Nov
Saltwater Serenity #392 - Ocean Views on Cudjoe Key

Seabreeze Escape WF RV Lot 489

Cudjoe Key
8.0 out of 10, Very good, (1)
The price is €221
includes taxes & fees
30 Nov - 1 Dec
Seabreeze Escape WF RV Lot 489

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates
8.4 out of 10, Very good, (117)
"Great experience "
United States
Peyton S.
The price is €477
includes taxes & fees
19 Nov - 20 Nov
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (120)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is €481
includes taxes & fees
18 Dec - 19 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

Galleon Getaway #533- Oceanfront Community

Cudjoe Key
The price is €478
includes taxes & fees
30 Nov - 1 Dec
Galleon Getaway #533- Oceanfront Community

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
Cudjoe Key
9.0 out of 10, Wonderful, (7)
"Great place! Perfect location"
United States
Troy B.
The price is €677
includes taxes & fees
18 Dec - 19 Dec
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Venture Out RV lot 223

Cudjoe key
7.4 out of 10, Good, (3)
"We really like the location."
United States
Zunen C.
The price is €243
includes taxes & fees
29 Nov - 30 Nov
Venture Out RV lot 223

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is €543
includes taxes & fees
23 Nov - 24 Nov
Island Time #110 Ocean Views - Cudjoe Key

Sailfish Haven #390 - Ocean Views, 35' seawall

Cudjoe Key
8.8 out of 10, Excellent, (6)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is €545
includes taxes & fees
19 Nov - 20 Nov
Sailfish Haven #390 - Ocean Views, 35' seawall

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

2.0 star property
Cudjoe Key
The price is €520
includes taxes & fees
19 Nov - 20 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key
9.6 out of 10, Exceptional, (7)
"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.
The price is €548
includes taxes & fees
30 Nov - 1 Dec
Reel Island Retreat #273 at Venture Out in the Florida Keys
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 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, apart-hotels, 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 €224 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.

How many holiday rentals are there in Summerland Key?

Choose from 496 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

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