Summerland Key Holiday Rentals

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Holiday Rentals in Summerland Key

Holiday Home in Summerland Key

8.2 out of 10, Very good, (98)
"Thank you so much for the great stay! The ocean view was beautiful! The landscaping with surrounding trees and flowers was lovely! The house was comfortable and had everything that we needed. It was perfect for our family!"
United States
Deidra B.
Private Secluded Ocean View & Pool Near Key West

Holiday Home in Little Torch Key

9.6 out of 10, Exceptional, (85)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
The price is AU$1,357
includes taxes & fees
26 Dec - 27 Dec
Old Florida Style, wrap around porch, boat basin for dockage, open water

Cottage in Cudjoe Key

9.0 out of 10, Wonderful, (159)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage in Cudjoe Key

8.8 out of 10, Excellent, (89)
"Nice place to vacation "
United States
Kevin D.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Holiday Home in Cudjoe Key

9.6 out of 10, Exceptional, (47)
"We had an awesome week at this property. I highly recommend this property ... fantastic communication, clean and exactly as described on the listing. "
United States
Mandy P.
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Holiday Home in Little Torch Key

10.0 out of 10, Exceptional, (1)
"We loved the house and the host were amazing and very helpful with giving us fishing and location spots to visit! We cant wait to come back! "
United States
Callie O.
Tranquility Bayview House-Ocean Front with boat basin and boat ramp

Holiday Home in Cudjoe Key

9.8 out of 10, Exceptional, (197)
"What we love about it was how close it was to Key West and that we had our own dock to put our boat in."
United States
Antuanett I.
Relax by Florida Keys Beaches, just a 7-min drive away

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (74)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in 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.

Mobile Home in 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

Holiday Home in Cudjoe Key

8.8 out of 10, Excellent, (148)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Holiday Home in Cudjoe Key

9.2 out of 10, Wonderful, (46)
"Everything went great. Enjoyed our time "
United States
Lisa B.
Canal front home @ Venture Out Resort in the Florida Keys!

Cottage in Cudjoe Key

9.0 out of 10, Wonderful, (88)
"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.
Canal front, dockage, 2 bedroom, 2 bath

Holiday Home in Little Torch Key

9.0 out of 10, Wonderful, (106)
"Horrible stay house was disgusting and nothing worked. Never book here!"
United States
Dep B.
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS

Cottage in Cudjoe Key

9.0 out of 10, Wonderful, (51)
"Check in was easy, place nice & quiet. Kitchen facilities was good. Had a problem with the microwave, property manager took care of it within hours. WiFi great. Access was easy once you got used to it."
United States
myra c.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (175)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
Waterfront Home

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (52)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Little Torch Key

8.6 out of 10, Excellent, (192)
"Great location"
United States
Kimberly W.
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (151)
"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 AU$391
includes taxes & fees
15 Dec - 16 Dec
Cottage with Pool and Boat Dockage just minutes to Key West!

Holiday Home in Cutthroat Harbor Estates

✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️
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$391 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?

Private Secluded Ocean View & Pool Near Key West: This highly rated holiday home rental in Summerland Key is located near the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, 1 hot tub and table football so that you can immerse yourself in your holiday. Some other top choices in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS.

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?

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