Search Vacation Homes in Summerland Key
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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.
$547 nightly
The price is $609
Jan 10 - Jan 11, 2026
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
$733 nightly
The price is $824
Dec 22 - Dec 23
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, (122)
"We enjoyed our stay! Great little house and location. "
Lisa K.
$461 nightly
The price is $511
Dec 22 - Dec 23
Total with taxes and fees
The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key WestUpper Sugarloaf Key
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
Jonathan L.
$2,063 nightly
The price is $2,284
Jan 3 - Jan 4, 2026
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.
$551 nightly
The price is $613
Jan 15 - Jan 16, 2026
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
$550 nightly
The price is $611
Jan 4 - Jan 5, 2026
Total with taxes and fees
Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
$658 nightly
The price is $731
Dec 22 - Dec 23
Total with taxes and fees
The Lighthouse - Beach Houses Key West
The Lighthouse - Beach Houses Key WestUpper Sugarloaf Key
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
Peter Q.
$1,571 nightly
The price is $1,741
Dec 24 - Dec 25
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
Looe Key Reef Resort
10/10 Excellent
Find out more about Summerland Key
Summerland Key Vacation Homes information
Number of reviews | 541 |
|---|---|
Accommodation | 411 Vacation Homes |
Lowest Price | $511 |
Highest Price | $2,284 |
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