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Our top choices for Summerland Key vacation homes

9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is ¥31,054
¥77,128 total
includes taxes & fees
Mar 5 - Mar 6
$$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
The price is ¥39,080
¥104,981 total
includes taxes & fees
Mar 3 - Mar 4
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is ¥32,771
¥95,856 total
includes taxes & fees
Mar 4 - Mar 5
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is ¥38,856
¥86,841 total
includes taxes & fees
Mar 3 - Mar 4
$$ SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Vacation Home in Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is ¥54,618
¥106,817 total
includes taxes & fees
Mar 11 - Mar 12
Spanish Queen @Venture Out, Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is ¥53,252
¥121,393 total
includes taxes & fees
Mar 4 - Mar 5
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
9.4 out of 10, Exceptional, (8 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is ¥31,132
¥94,949 total
includes taxes & fees
Mar 11 - Mar 12
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
7.8 out of 10, Good, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is ¥38,622
¥79,654 total
includes taxes & fees
Mar 7 - Mar 8
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Vacation Home in Cudjoe Key

Fun in the Sun in Cudjoe Key! #51
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is ¥35,892
¥107,948 total
includes taxes & fees
Mar 9 - Mar 10
Fun in the Sun in Cudjoe Key! #51

Vacation Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is ¥188,821
¥311,350 total
includes taxes & fees
Mar 9 - Mar 10
Private and Exclusive Florida Keys Getaway
9.0 out of 10, Wonderful, (159 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is ¥54,618
¥108,884 total
includes taxes & fees
Mar 25 - Mar 26
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is ¥47,595
¥86,043 total
includes taxes & fees
Mar 31 - Apr 1
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
8.8 out of 10, Excellent, (66 reviews)
"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "
United States
Paula D.
The price is ¥109,079
¥241,859 total
includes taxes & fees
Mar 26 - Mar 27
One of the very few beach houses with a daily, rental license in the Keys.
8.4 out of 10, Very Good, (123 reviews)
"Great experience "
United States
Peyton S.
The price is ¥50,716
¥103,871 total
includes taxes & fees
Mar 3 - Mar 4
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is ¥188,821
¥316,208 total
includes taxes & fees
Mar 12 - Mar 13
The Lighthouse - Beach Houses Key West
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is ¥49,156
¥116,474 total
includes taxes & fees
Mar 31 - Apr 1
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Vacation Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is ¥222,293
¥363,208 total
includes taxes & fees
Mar 11 - Mar 12
The Hemingway - Beach Houses Key West
The price is ¥59,299
¥129,659 total
includes taxes & fees
Mar 12 - Mar 13
Starlight Serenity - Hideaway with Stunning Views
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful "
United States
Lisa P.
The price is ¥86,023
¥162,630 total
includes taxes & fees
Mar 30 - Mar 31
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is ¥71,764
¥136,255 total
includes taxes & fees
Apr 1 - Apr 2
Starlight Serenity - Hideaway w Stunning Views
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

Summerland Key Vacation Homes information

Number of reviews
659
Accommodation
411 Vacation Homes
Lowest Price
¥77,128
Highest Price
¥363,208