Summerland Key Holiday Rentals

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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Holiday Rentals in Summerland Key

Exterior
105 - Newly renovated house Oceanside and Pool
105 - Newly renovated house Oceanside and Pool
The price is HK$2,721
HK$5,959 total
includes taxes & fees
10 Nov - 11 Nov
105 - Newly renovated house Oceanside and Pool
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.2 out of 10, Very good, (47)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is HK$1,166
HK$2,613 total
includes taxes & fees
9 Nov - 10 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Swim-up bar
Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$3,936
HK$7,149 total
includes taxes & fees
10 Nov - 11 Nov
Atlantic View Luxury Villa with Pool
Pool
Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (157)
"Great location and very happy with our accommodations."
United States
Carrie B.
The price is HK$1,166
HK$2,466 total
includes taxes & fees
13 Nov - 14 Nov
Cottage with Pool and Dockage, just minutes to Key West
Outdoor dining
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
United States
Edward H.
The price is HK$1,158
HK$3,390 total
includes taxes & fees
9 Nov - 10 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor dining
Endless Summer Hideaway - lot 181
Endless Summer Hideaway - lot 181
The price is HK$777
HK$1,644 total
includes taxes & fees
6 Dec - 7 Dec
Endless Summer Hideaway - lot 181
Marina
Canal front lot only. No house or RV. You need to bring your RV.
Canal front lot only. No house or RV. You need to bring your RV.
The price is HK$1,158
HK$1,459 total
includes taxes & fees
7 Dec - 8 Dec
Canal front lot only. No house or RV. You need to bring your RV.
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
The price is HK$1,361
HK$3,046 total
includes taxes & fees
16 Nov - 17 Nov
Canal front, dockage, 2 bedroom, 2 bath
A heated pool
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
10.0 out of 10, Exceptional, (7)
"'Amazing' is the best word I have to describe this vacation rental. Three of us stayed and the house was perfect. Clean, comfortable (the adjustable beds are GREAT), quiet, roomy and perfectly located. Amazing views as well! Highly recommend. "
United States
Ivory C.
The price is HK$1,633
HK$5,010 total
includes taxes & fees
13 Nov - 14 Nov
Saltwater Serenity #392 - Ocean Views on Cudjoe Key
A heated pool
Reel Island Retreat #273 at Venture Out in the Florida Keys
Reel Island Retreat #273 at Venture Out in the Florida Keys
9.6 out of 10, Exceptional, (7)
"Very clean place"
United States
Michael T.
The price is HK$1,633
HK$5,080 total
includes taxes & fees
9 Nov - 10 Nov
Reel Island Retreat #273 at Venture Out in the Florida Keys
A heated pool
Mahi House #440 - 35' seawall
Mahi House #440 - 35' seawall
10.0 out of 10, Exceptional, (1)
"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "
United States
Emily P.
The price is HK$1,633
HK$5,010 total
includes taxes & fees
14 Nov - 15 Nov
Mahi House #440 - 35' seawall
A heated pool
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
2.0 star property
9.0 out of 10, Wonderful, (7)
"Great place! Perfect location"
United States
Troy B.
The price is HK$2,041
HK$5,593 total
includes taxes & fees
7 Nov - 8 Nov
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
A heated pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
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."
United States
Javier
The price is HK$1,469
HK$4,857 total
includes taxes & fees
12 Nov - 13 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool
Sailfish Haven #390 - Ocean Views, 35' seawall
Sailfish Haven #390 - Ocean Views, 35' seawall
8.8 out of 10, Excellent, (6)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is HK$1,633
HK$5,010 total
includes taxes & fees
16 Nov - 17 Nov
Sailfish Haven #390 - Ocean Views, 35' seawall
Terrace/patio
Seabreeze Escape WF RV Lot 489
Seabreeze Escape WF RV Lot 489
8.0 out of 10, Very good, (1)
The price is HK$1,088
HK$2,049 total
includes taxes & fees
7 Nov - 8 Nov
Seabreeze Escape WF RV Lot 489
Dining
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
10.0 out of 10, Exceptional, (2)
"Super spot and views of the Straits. Very clean with new modern appliances and amenities. Comfortable and relaxing. Roku TVs make it a challenge to watch major sporting events, but that’s not why we were there. Pool spa out of service due to “health concerns,” but the pool itself seemed ok. Overall, a peaceful and calm stay all about the soothing views with only the splashing sounds of the occasional fish chasing bait. "
United States
Anonymous traveller
The price is HK$3,878
HK$7,893 total
includes taxes & fees
30 Nov - 1 Dec
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Pool
Palm - Beach Houses Key West
Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
United States
Crystal G.
The price is HK$5,987
HK$11,896 total
includes taxes & fees
19 Nov - 20 Nov
Palm - Beach Houses Key West
A heated pool
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
9.8 out of 10, Exceptional, (10)
"Beautiful place!"
United States
Sara C.
The price is HK$3,061
HK$7,311 total
includes taxes & fees
10 Nov - 11 Nov
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
A heated pool
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
The price is HK$1,429
HK$4,788 total
includes taxes & fees
8 Nov - 9 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior detail
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
10.0 out of 10, Exceptional, (2)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is HK$1,951
HK$3,760 total
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom house with WiFi, AC in lovely 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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Everything was excellent 5 stars we stayed at a lot of resorts this was best by far Sue was very helpful and even talked with cleaning staff was so friendly. They ALL go above and beyond. Will be back to our private little getaway."
Karen 9-night trip
Posted 7 days ago
Parmer's Resort

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:

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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?

Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes: This highly rated holiday home rental in Summerland Key is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other top choices in Summerland Key are Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill and COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!.

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?

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.