Summerland Key Holiday Rentals

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Check prices for these dates

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
12 Sept - 14 Sept
Next weekend
19 Sept - 21 Sept

Holiday Rentals in Summerland Key

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

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

9.6 out of 10, Exceptional, (79)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Springs Venture Out Dolphin House (#386) with beautiful open water views
Outdoor pool, a heated pool

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

9.2 out of 10, Wonderful, (100)
"We absolutely loved our time here! GORGEOUS view of the bay! It was exactly what we needed for our guys trip!"
Springs Venture Out Dolphin House (#386) with beautiful open water views
✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️
Terrace/patio

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

✨️ Ocean access w/Dock, 4 bed/4 bath. Inquire for any special requests ✨️
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

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
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

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."
Canal front, dockage, 2 bedroom, 2 bath
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (86)
"Quiet and off the beaten path, old school, old style Key’s homes,would stay again."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, beach towels

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 HK$2,728
HK$6,372 total
includes taxes & fees
12 Sept - 13 Sept
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
A Tropical Luxury Getaway, Your own private resort!!
Outdoor pool, a heated pool

A Tropical Luxury Getaway, Your own private resort!!

10.0 out of 10, Exceptional, (38)
"The house and pool were very nice."
A Tropical Luxury Getaway, Your own private resort!!
Quaint cottage, pool, dockage just minutes to Key West!
Miscellaneous

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

9.0 out of 10, Wonderful, (141)
"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!
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Beach nearby, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (122)
"We loved having our own space for a boat. Great location."
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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

8.6 out of 10, Excellent, (146)
"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. "
Cottage with Pool and Boat Dockage just minutes to Key West!
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (169)
"Great price great location "
Waterfront Home
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
A heated pool

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

9.8 out of 10, Exceptional, (8)
"Beautiful place!"
The price is HK$2,883
HK$6,372 total
includes taxes & fees
11 Sept - 12 Sept
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

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

10.0 out of 10, Exceptional, (3)
"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. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (152)
"The place was spacious, very clean and beautiful!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

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 Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (152)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (59)
"Great place to take the boat"
20 MINUTES TO KEY WEST , BOATERS PARADISE
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool

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

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!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is HK$1,902
HK$4,634 total
includes taxes & fees
10 Sept - 11 Sept
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
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

Find out more about Summerland Key

Search for holiday rentals in Summerland Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Summerland Key using one of the methods below:

  • View our selection of featured holiday rentals in Summerland Key
  • Use the map to find apartments and other holiday homes in the Summerland Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Summerland Key while they last

Look no further and take a look at our great range of rental properties in Summerland Key!

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

How many holiday rentals are there in Summerland Key?

Choose from 483 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.