Summerland Key Vacation Rentals from ￥50,669: Search Short-Term Rentals

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Vacation Rentals in Summerland Key

"The secluded dock is a nice feature. The driveway is tricky to exit. "

￥115,314 total

includes taxes & fees

Nov 8 - Nov 9

"Very nice community. Has everything you need for a nice vacation. Beautiful pool, ocean swimming, nice quiet area and very secure.Home was nicely decorated and very clean. Beds were very comfortable "

"Great place to stay. Very secure and comfortable."

"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."

"Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience "

"Clean and comfortable."

"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "

"Quiet and off the beaten path, old school, old style Key’s homes,would stay again."

"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."

"Was such a great stay clean and everything we needed "

￥50,669 total

includes taxes & fees

Oct 19 - Oct 20

"We had an excellent time , property was an excellent place for our vacation.We hope to come back next year"

"Lovely property. Well equipped, nicely decorated, perfect for our stay."

￥124,550 total

includes taxes & fees

Oct 15 - Oct 16

"Clean bungalo perfect for a fishing vacation. I look forward to staying here again!"

"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. "

"30 minutes to Key West; great local restaurants (highly recommend the Square Grouper) and within minutes of biking/walking trails. A wonderful location and a well appointed house. We loved it!"

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

￥82,125 total

includes taxes & fees

Oct 15 - Oct 16

"Clean place with room for 2 couples. Everything you need."

￥63,941 total

includes taxes & fees

Oct 19 - Oct 20

"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!"

￥53,221 total

includes taxes & fees

Oct 23 - Oct 24

"We had a great time and will be back. "

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Top Summerland Key Hotel Reviews

Parmer's Resort

10/10 Excellent

"Excellent laid back property. Close to a good restaurant "

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

10/10 Excellent

"This home was a 10/10 experience. Everything was top notch from the cleanliness to the amenities available. It looks exactly like the pictures online but in person it was so much better. The view from the balcony was the best part about it as well as the boat access. We also spent lots of time at the pool on the property which was super clean and refreshing after being on the water all day. Everyone in venture out was super friendly and we rented bikes from Big Pine Bike Rental to ride around the property. Our dog enjoyed the stay too. Being able to grill and cook at home was a major plus. The home is extremely well cared for and we will be back to stay again. "

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

10/10 Excellent

"Cute, cozy and clean! This cottage is perfect for a couples getaway! Inside had everything we needed for our trip. Location is convenient to stores and restaurants and not far from Key West. Boat launch/parking and trailer parking provided so that saves money! We would definitely stay again. "

Looe Key Reef Resort

8/10 Good

"This is a very REASONABLY priced lodging for the FL Keys so expect simple things. We had a great stay, room was clean, the young gent at the front desk was exceptionally friendly and helpful, ditto at checkout. The beds are comfortable. The shower head had great pressure and the onsite tiki bar is a big plus. There were no plastic cups or coffee maker in the room but there was a microwave and fridge and table with two chairs. The ice machine was not working but there is a quickie mart just next door for that if you needed it. Could the resort be flashier, yes it could but Looe Key Reef Resort offered us a cost effective comfy safe stay in a place where time in the room was not important. We did not use the pool or the dive/snorkle amenities as we came down to fish, but if you wanted that stuff it’s all here. We hope to be back soon."

Find out more about Summerland Key

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Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Old Florida Style, wrap around porch, boat basin for dockage, open water: This Summerland Key vacation home rental 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 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 vacation rentals are there in Summerland Key?

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

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 vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.

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Summerland Key Vacation Rentals

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Vacation Rentals in Summerland Key

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

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

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

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

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

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

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

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

Canal front, dockage, 2 bedroom, 2 bath

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

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

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

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

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

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

Relax by Florida Keys Beaches, just a 7-min drive away

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

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

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

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

Top Summerland Key Hotel Reviews

Parmer's Resort

Sugarloaf Key Hotel at KOA Resort

Sugar Loaf Lodge

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

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

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

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

Looe Key Reef Resort

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

Find out more about Summerland Key

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