Summerland Key Holiday Rentals

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Holiday Rentals in Summerland Key

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
10.0 out of 10, Exceptional, (4)
"Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience "
United States
Debbie W.
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (153)
"The property was excellent. The location was perfect. Quiet and relaxing. "
United States
Jonathan K.
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
9.6 out of 10, Exceptional, (45)
"Loved it! The view is unbelievable! Such a such place and tastefully decorated. Beds were comfy and it had just what we needed to cook. Nice big table to play games. We will definitely book again! "
United States
Jennifer B.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
8.8 out of 10, Excellent, (147)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
United States
Charles V.
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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 NZ$560
includes taxes & fees
30 Nov - 1 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cudjoe Key
8.6 out of 10, Excellent, (150)
"An amazing place to come home to after a long day in the keys. Having a car is a must, but I would recommend time after time again and hope to come back again in the future"
United States
Travis W.
Cottage with Pool and Boat Dockage just minutes to Key West!

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

Cudjoe Key
8.8 out of 10, Excellent, (73)
"Place was everything we needed, would definitely stay again "
United States
James h.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

Cudjoe Key
9.8 out of 10, Exceptional, (213)
"Awesome location, lots of amenities, lots of rules too so be aware! House was super clean and well stocked, Last Key Realty was very helpful and responsive!"
United States
Marti B.
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
9.8 out of 10, Exceptional, (229)
"My mom and I were absolutely amazed by the property, we loved everything and hope to come back again!"
United States
Emma T.
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key
9.0 out of 10, Wonderful, (158)
"Wonderful stay with great property and pool. Very well maintained!"
United States
Eric E.
Cottage with swimming pool and dockage, just minutes to Key West!

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key
8.6 out of 10, Excellent, (192)
"Wonderful, cozy cottage facing sunrise on the water. We had very efficient communication with the property manager for any details. Dog friendly, designated parking, great full kitchen and room for at least 3 adults. I would definitely recommend this location, we will be back!"
United States
Suzanne R.
Direct Oceanfront Cottage-Sunrise View- #2,

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
9.6 out of 10, Exceptional, (85)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is NZ$1,383
includes taxes & fees
24 Nov - 25 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Quaint cottage, pool, dockage just minutes to Key West!

Cudjoe Key
9.0 out of 10, Wonderful, (143)
"My family loved the cottage. The pool and fishing dock were awesome."
United States
Leslie B.
Quaint cottage, pool, dockage just minutes to Key West!

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

Cudjoe Key
8.8 out of 10, Excellent, (88)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
United States
Mitchell D O.
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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

Cudjoe Key
8.8 out of 10, Excellent, (89)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
United States
James P.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Cudjoe Key
10.0 out of 10, Exceptional, (31)
"Very clean, it hit all the things we wanted i.e. upstairs outdoor porch. "
United States
Kevin S.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft

Cudjoe Key
9.4 out of 10, Exceptional, (164)
"The space and location were perfect for my husband and I. We brought our pontoon and it was nice to launch 3 blocks from the property and to park at the dock, at the house. We enjoyed the pool and the beautiful area. The owner kept in contact with us and was wonderful to communicate with. We would stay at this property again. "
United States
Tina
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft

Waterfront Home

Cudjoe Key
8.6 out of 10, Excellent, (173)
"Venture out is more of a retirement community than a family resort. The location is ideal and the house was well appointed "
United States
CAROLINE L.
Waterfront Home

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
The price is NZ$692
includes taxes & fees
16 Nov - 17 Nov
Canal front, dockage, 2 bedroom, 2 bath

Keys House - Venture Out Lot 220

2.5 star property
Summerland Key
9.8 out of 10, Exceptional, (6)
"Nice location! Great balcony!"
United States
Maso O.
Keys House - Venture Out Lot 220
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 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 NZ$560 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 498 Expedia holiday rentals in Summerland Key for a memorable holiday.

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 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.