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Our top choices for Summerland Key vacation homes
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
Davian k.
$391 nightly
The price is $434
Dec 14 - Dec 15
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
$574 nightly
The price is $646
Dec 15 - Dec 16
Total with taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key CottageSummerland Key
9.8 out of 10, Exceptional, (121)
"We enjoyed our stay! Great little house and location. "
Lisa K.
$463 nightly
The price is $513
Dec 14 - Dec 15
Total with taxes and fees
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
Ubaldo G.
$504 nightly
The price is $560
Dec 14 - Dec 15
Total with taxes and fees
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
Tammy G.
$585 nightly
The price is $650
Dec 15 - Dec 16
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming poolCutthroat Harbor Estates
8.4 out of 10, Very Good, (118)
"Great experience "
Peyton S.
$483 nightly
The price is $536
Dec 15 - Dec 16
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe Key
$533 nightly
The price is $592
Dec 14 - Dec 15
Total with taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!Cudjoe Key
7.6 out of 10, Good, (13)
"Good experience. The property is well place and the Venture is really nice and quiet."
Primeau J.
$432 nightly
The price is $480
Jan 6 - Jan 7, 2026
Total with taxes and fees
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.
Top Summerland Key Hotel Reviews
Sugar Loaf Lodge
10/10 Excellent
Find out more about Summerland Key
Summerland Key Vacation Homes information
Number of reviews | 576 |
|---|---|
Accommodation | 411 Vacation Homes |
Lowest Price | $434 |
Highest Price | $2,284 |
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