Summerland Key Holiday Rentals from €526: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Summerland Key

Relax on the waterfront with Adirondack chairs and a small dining table.

"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "

"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "

Enjoy stunning ocean views from the balcony of this beachfront property, featuring a spacious living area with large windows and comfortable outdoor seating.

"Great price great location "

Enjoy a tranquil beachside retreat with access to the calm sea and nearby amenities.

"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "

Enjoy cooking and dining in this well-equipped kitchen with a central island, oven, and ample counter space.

"The place was spacious, very clean and beautiful!"

includes taxes & fees

3 Aug - 4 Aug

Relax by the pool surrounded by lush palm trees.

"The place was everything as described. Close enough to Key West and beaches that we did not stay home much during the day but nice to have a peaceful place to land in the evenings. Bedrooms and bathrooms were right but served its purpose. Jennifer and Susan were very helpful with check in. Thanks for letting my parents relive their glory days in the Keys. I would stay again if we come back!"

Enjoy ocean views from the spacious balcony and covered porch of this coastal retreat.

"Home was clean and great location! Would definitely stay here again! "

Enjoy a serene beach experience with a clear ocean view, lounge chairs, and a dock for water activities.

"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. "

Enjoy cooking in this well-equipped kitchen with a central island and standard appliances.

"It was a beautiful home and Francine, our host, was most accommodating."

"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."

Guests can enjoy a serene waterfront experience from this tranquil dock surrounded by lush greenery.

"Deer in the front yard, perfect location, clean and friendly "

includes taxes & fees

2 Aug - 3 Aug

Relax by the pool surrounded by palm trees and lounge chairs.

" Fantastic hidden gem in Summerland Key. A perfect location for us close to family who live nearby. Ocean Breeze contains everything you need for a getaway - comfy beds, a fully stocked kitchen, entertainment and plenty of space! "

Enjoy waterfront views and access to a marina from this coastal property.

"Comfortable and very well appointed! High end amenities, and very responsive host ensured our stay was a memorable one. Our third time booking this property and can’t think of anything they could improve!"

Enjoy an outdoor space with a swimming pool and lush greenery surrounding this two-story house.

"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "

"Our stay was very pleasant."

"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "

Relax by the pool surrounded by palm trees and lounge chairs, with a clear view of the sea.

"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "

includes taxes & fees

19 Aug - 20 Aug

Relax by the serene pool surrounded by lush palm trees.

"The house and pool were very nice."

Relax by the pool surrounded by lush greenery and a thatched-roof gazebo.

"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"

includes taxes & fees

12 Aug - 13 Aug

Enjoy waterfront views from the balcony of this two-story property, situated along a tranquil canal with a boat docked at the water's edge.

"This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and"

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"It was great"

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

10/10 Excellent

"Our trip was so good we were already talking about booking it for next year!Mike and Carol were great to work with. I’ve never had someone so quick to respond, take care of any issues, and provide recommendations during a stay.Their home was a perfect place for us and convenient to so much throughout the keys. It was clean, spacious, and had everything you could want or need during your stay. The kitchen was fully stocked with everything you could think of. The appliances were great with a dishwasher, washer, and dryer on hand. Underneath is a grill, bikes, helmets, kayaks, life jackets, fishing equipment, chairs, a cooler, etc. They have everything you need!The resort has a community store, that my kids would bike to sometimes multiple times per day. There’s a pool, boat ramp, and tiki huts to hang out under!We spent much of our time at Bahia Honda state park at one of the most beautiful beaches I’ve ever been to, snorkeling, soaking up the sun, and taking in the breathtaking views. My oldest son and I did a party fishing charter (Gulfstream IV - highly recommended) and my wife and youngest son went to the Turtle Hospital in Marathon (highly recommended). We made a couple trips to Key West, which is a short drive away, to shop, see the sights, and had some of the best food I’ve ever had (great recommendations from Mike). It truly was a memorable vacation and we owe a lot of it to Mike and Carol for allowing us to use their wonderful home! Thank you!"

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

10/10 Excellent

"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

10/10 Excellent

"Overall, my family had a great time staying at this location. We enjoyed using the pool and kayaks. It didn’t have an actual paddle board as stated and my daughter was disappointed with that. My husband really enjoyed fishing from the dock. He caught a variety of fish. The house was clean and modern. Plenty of space for us. There was a variety of products available at the home for us to use. Lactation isn’t too far from Key West. We would definitely stay here again ‘ "

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 €526 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 JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community! and Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West.

How many holiday rentals are there in Summerland Key?

Choose from 480 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Summerland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Summerland Key

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

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

Waterfront Home

Direct Oceanfront Cottage-Sunrise View- #2,

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

Canal front, dockage, 2 bedroom, 2 bath

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Private Secluded Ocean View & Pool Near Key West

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

OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

20 MINUTES TO KEY WEST , BOATERS PARADISE

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

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

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

Island Time #110 Ocean Views - Cudjoe Key

A Tropical Luxury Getaway, Your own private resort!!

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

waterfront cottage near key west, sleeps 6

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugarloaf Key Hotel at KOA Resort

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Parmer's Resort

Direct Oceanfront Cottage-Sunrise View- #2,

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

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

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

Waterfront Home

Find out more about Summerland Key

Frequently asked questions

Expedia's Latest Trends