Search Vacation Homes in Summerland Key

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

105 - Newly renovated house Oceanside and Pool

Cudjoe Key
The price is HK$2,720
HK$5,965 total
includes taxes & fees
23 Nov - 24 Nov
105 - Newly renovated house Oceanside and Pool

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
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$3,381 total
includes taxes & fees
24 Nov - 25 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
Cudjoe Key
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$4,614 total
includes taxes & fees
14 Nov - 15 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
Cudjoe Key
9.4 out of 10, Exceptional, (10)
"Greta property, really enjoyed the water view and the bbq grill "
United States
William B.
The price is HK$1,632
HK$4,813 total
includes taxes & fees
14 Nov - 15 Nov
Island Time #110 Ocean Views - Cudjoe Key

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"Great property, owners were very helpful and we really enjoyed our stay!"
United States
Lee J.
The price is HK$1,702
HK$4,072 total
includes taxes & fees
16 Nov - 17 Nov
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

2.0 star property
Cudjoe Key
The price is HK$1,428
HK$4,568 total
includes taxes & fees
25 Nov - 26 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key
9.6 out of 10, Exceptional, (7)
"Very clean place"
United States
Michael T.
The price is HK$1,632
HK$4,813 total
includes taxes & fees
25 Nov - 26 Nov
Reel Island Retreat #273 at Venture Out in the Florida Keys

Mahi House #440 - 35' seawall

Cudjoe Key
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$1,632
HK$4,813 total
includes taxes & fees
30 Nov - 1 Dec
Mahi House #440 - 35' seawall

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

Summerland Key
8.8 out of 10, Excellent, (64)
"We had a wonderful stay. The house was so inviting and the view was spectacular. I would strongly suggest that some work be done in the kitchen. Frying pans were warped, counter oven had a sprung door, toaster only worked on one side. Also, the bunk beds needed tightening. They were a little scary. Yes, I would go back again. "
United States
Meredith A.
One of the very few beach houses with a daily, rental license in the Keys.

Sailfish Haven #390 - Ocean Views, 35' seawall

Cudjoe Key
8.8 out of 10, Excellent, (6)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is HK$1,632
HK$4,813 total
includes taxes & fees
25 Nov - 26 Nov
Sailfish Haven #390 - Ocean Views, 35' seawall

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

2.0 star property
Cudjoe Key
The price is HK$1,632
HK$4,751 total
includes taxes & fees
25 Nov - 26 Nov
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Cudjoe Key
The price is HK$1,510
HK$4,660 total
includes taxes & fees
13 Nov - 14 Nov
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Galleon Getaway #533- Oceanfront Community

Cudjoe Key
The price is HK$1,142
HK$4,208 total
includes taxes & fees
30 Nov - 1 Dec
Galleon Getaway #533- Oceanfront Community

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

Cutthroat Harbor Estates
8.4 out of 10, Very good, (117)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
United States
Kiril
The price is HK$1,749
HK$4,190 total
includes taxes & fees
21 Nov - 22 Nov
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Cudjoe Key
9.4 out of 10, Exceptional, (27)
"Lovely property by the water in Cudjoe Key. Very comfortable and well equipped. Host was very communicative and location was great for getting to Key West and other local attractions. Would definitely stay again! "
United Kingdom
Tom K.
The price is HK$1,836
HK$5,050 total
includes taxes & fees
17 Nov - 18 Nov
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

2.0 star property
Cudjoe Key
The price is HK$2,040
HK$5,264 total
includes taxes & fees
13 Nov - 14 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (120)
"Great location for some much needed time away."
United States
Brad R.
The price is HK$1,943
HK$4,468 total
includes taxes & fees
30 Nov - 1 Dec
Kelly's Kabin - Adorable Private Summerland Key Cottage

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
Cudjoe Key
9.0 out of 10, Wonderful, (7)
"Great place! Perfect location"
United States
Troy B.
The price is HK$1,836
HK$5,011 total
includes taxes & fees
30 Nov - 1 Dec
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

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

Little Torch Key
9.6 out of 10, Exceptional, (84)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is HK$2,332
HK$5,362 total
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key
The price is HK$1,346
HK$4,453 total
includes taxes & fees
25 Nov - 26 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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

Summerland Key Vacation Homes information

Number of reviews
627
Accommodation
388 Vacation Homes
Lowest Price
HK$3,381
Highest Price
HK$5,362