Holiday Homes in Summerland Key

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Our top choices for Summerland Key holiday homes

9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is AU$689
includes taxes & fees
5 Mar - 6 Mar
$$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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 AU$866
includes taxes & fees
4 Mar - 5 Mar
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
The price is AU$944
includes taxes & fees
3 Mar - 4 Mar
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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 AU$791
includes taxes & fees
3 Mar - 4 Mar
$$ SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is AU$1,073
includes taxes & fees
4 Mar - 5 Mar
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Holiday 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 AU$949
includes taxes & fees
11 Mar - 12 Mar
Spanish Queen @Venture Out, 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 AU$728
includes taxes & fees
7 Mar - 8 Mar
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
9.4 out of 10, Exceptional, (8 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AU$846
includes taxes & fees
11 Mar - 12 Mar
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Holiday 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 AU$956
includes taxes & fees
9 Mar - 10 Mar
Fun in the Sun in Cudjoe Key! #51

Holiday 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 AU$2,826
includes taxes & fees
9 Mar - 10 Mar
Private and Exclusive Florida Keys Getaway
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 AU$759
includes taxes & fees
31 Mar - 1 Apr
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
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 AU$965
includes taxes & fees
25 Mar - 26 Mar
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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 AU$2,120
includes taxes & fees
26 Mar - 27 Mar
One of the very few beach houses with a daily, rental license in the Keys.
9.4 out of 10, Exceptional, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AU$907
includes taxes & fees
1 Apr - 2 Apr
Island Time #110 Ocean Views - Cudjoe Key

Holiday 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 AU$2,870
includes taxes & fees
12 Mar - 13 Mar
The Lighthouse - Beach Houses Key West
8.4 out of 10, Very good, (123 reviews)
"Great experience "
United States
Peyton S.
The price is AU$933
includes taxes & fees
3 Mar - 4 Mar
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is AU$952
includes taxes & fees
1 Apr - 2 Apr
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Holiday 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 AU$3,241
includes taxes & fees
11 Mar - 12 Mar
The Hemingway - Beach Houses Key West
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful "
United States
Lisa P.
The price is AU$1,442
includes taxes & fees
30 Mar - 31 Mar
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
8.0 out of 10, Very good, (1 review)
The price is AU$956
includes taxes & fees
4 Mar - 5 Mar
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
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 Holiday Homes information

Number of reviews
671
Accommodation
411 Holiday Homes
Lowest Price
AU$689
Highest Price
AU$3,241