Summerland Key Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Summerland Key

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

9.6 out of 10, Exceptional, (80)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
Old Florida Style, wrap around porch, boat basin for dockage, open water

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

9.0 out of 10, Wonderful, (88)
"Quiet and off the beaten path, old school, old style Key’s homes,would stay again."
The price is NZ$605
includes taxes & fees
7 Oct - 8 Oct
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
Charming cottages, dockage, pool, just minutes to Key West

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (162)
"The property is ideally situated, providing convenient access to key destinations within the Florida Keys. While the residence may benefit from some modernization, its value proposition remains highly competitive."
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (9)
"Beautiful place!"
The price is NZ$1,408
includes taxes & fees
29 Sept - 30 Sept
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (192)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

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."
The price is NZ$644
includes taxes & fees
29 Sept - 30 Sept
Canal front, dockage, 2 bedroom, 2 bath

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

8.8 out of 10, Excellent, (87)
"We had a great time and will be back. "
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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

9.0 out of 10, Wonderful, (155)
"Clean and comfortable."
Cottage with swimming pool and dockage, just minutes to Key West!

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

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

9.0 out of 10, Wonderful, (142)
"We had an excellent time , property was an excellent place for our vacation.We hope to come back next year"
Quaint cottage, pool, dockage just minutes to Key West!

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.6 out of 10, Exceptional, (29)
"Perfect little place. "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
The price is NZ$1,417
includes taxes & fees
29 Sept - 30 Sept
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

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

9.8 out of 10, Exceptional, (229)
"Perfect location. Very affordable and very well cared for. Short drive to Key West or any other things you may want to do in the Keys. Nice community swimming pool and sure. Great access to the water for boating or fishing."
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

9.8 out of 10, Exceptional, (123)
"We loved having our own space for a boat. Great location."
Mini lobster available! Open Water View from porch , dock, bikes, kayaks

Springs Venture Out Dolphin House (#386) with beautiful open water views

9.2 out of 10, Wonderful, (100)
"We had a very relaxing time here. VO is convenient to many locations and activities. Unfortunately the weather wasn’t the best for the first few days but we still were able to enjoy fishing from the dock and relaxing by the pool. The morning sunrise views were beautiful. "
Springs Venture Out Dolphin House (#386) with beautiful open water views

Waterfront Haven House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (16)
"Beautiful place, quiet"
Waterfront Haven House with Boat Basin & Ramp!

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

8.8 out of 10, Excellent, (146)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

8.8 out of 10, Excellent, (64)
"Not enough furniture,no railing on dock, or light for night fishing.pool my have popped out , just patched it up and pour concrete around it, property is neglected, could and should be so much more!great to watch the grandkids in the pool,or fishing on the dock, all from the porch"
The price is NZ$2,280
includes taxes & fees
29 Sept - 30 Sept
One of the very few beach houses with a daily, rental license in the Keys.

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

9.6 out of 10, Exceptional, (42)
"Great place to stay. Very secure and comfortable."
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Summerland Key Hotel Reviews

Find out more about Summerland Key

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$605 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.

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 484 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.