Summerland Key Holiday Rentals

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Holiday Rentals in Summerland Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (51)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Michele S.
The price is AU$543
includes taxes & fees
23 Oct - 24 Oct
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (98)
"Clean place with room for 2 couples. Everything you need."
Jason W.
The price is AU$661
includes taxes & fees
22 Oct - 23 Oct
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
Mark F.
The price is AU$696
includes taxes & fees
20 Oct - 21 Oct
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (155)
"Stayed 13 days perfect location and this was our second stay at Cudjoe Cottages. Was able to dock boat here but had to put in at Cudjoe Gardens marina, just 5 minutes away. Basic old school Florida key’s cottages,clean and inexpensive. Nice community pool also. Definitely will stay again."
Anonymous traveller
The price is AU$493
includes taxes & fees
26 Oct - 27 Oct
Cottage with Pool and Dockage, just minutes to Key West
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (86)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
Jennifer D.
The price is AU$611
includes taxes & fees
16 Nov - 17 Nov
Canal front, dockage, 2 bedroom, 2 bath
Canal front lot only. No house or RV. You need to bring your RV.
The price is AU$291
includes taxes & fees
18 Oct - 19 Oct
Canal front lot only. No house or RV. You need to bring your RV.
Endless Summer Hideaway - lot 181
The price is AU$330
includes taxes & fees
26 Oct - 27 Oct
Endless Summer Hideaway - lot 181
Atlantic View Luxury Villa with Pool
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
Preetam
Atlantic View Luxury Villa with Pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
9.2 out of 10, Wonderful, (7)
"Good location"
Chancey C.
The price is AU$913
includes taxes & fees
18 Oct - 19 Oct
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Beach Getaway in the Florida Keys
8.4 out of 10, Very good, (7)
"Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!"
Robyn M.
The price is AU$3,695
includes taxes & fees
5 Nov - 6 Nov
Beach Getaway in the Florida Keys
Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
9.8 out of 10, Exceptional, (9)
"Greta property, really enjoyed the water view and the bbq grill "
William B.
The price is AU$913
includes taxes & fees
20 Oct - 21 Oct
Island Time #110 Ocean Views - Cudjoe Key
Saltwater Serenity #392 - Ocean Views on 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 "
Anonymous traveller
The price is AU$943
includes taxes & fees
22 Oct - 23 Oct
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
Jeannine R.
The price is AU$644
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
2.0 star property
9.0 out of 10, Wonderful, (7)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
Rebecca G.
The price is AU$954
includes taxes & fees
18 Oct - 19 Oct
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
2.0 star property
The price is AU$965
includes taxes & fees
18 Oct - 19 Oct
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Seabreeze Escape WF RV Lot 489
8.0 out of 10, Very good, (1)
The price is AU$409
includes taxes & fees
26 Oct - 27 Oct
Seabreeze Escape WF RV Lot 489
Venture Out RV lot 223
7.4 out of 10, Good, (3)
"We really like the location."
Zunen C.
The price is AU$378
includes taxes & fees
7 Nov - 8 Nov
Venture Out RV lot 223
Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
Emily P.
The price is AU$944
includes taxes & fees
18 Oct - 19 Oct
Mahi House #440 - 35' seawall
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (117)
"Deer in the front yard, perfect location, clean and friendly "
Sara H.
The price is AU$837
includes taxes & fees
18 Oct - 19 Oct
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Reel Island Retreat #273 at Venture Out in the Florida Keys
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. "
Lindsay C.
The price is AU$959
includes taxes & fees
18 Oct - 19 Oct
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, 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 favourite 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 depend 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 AU$520 per night. Entering your travel dates in the search wizard might find you 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.

What are some of the best holiday rentals that Summerland Key has to offer?

Old Florida Style, wrap around porch, boat basin for dockage, open water: This highly rated holiday home rental in Summerland Key is located by the ocean, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family. Some other top choices in Summerland Key are Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community and Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West.

How many holiday rentals are there in Summerland Key?

Choose from 494 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Sugarloaf Beach 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.