Search Summerland Key pet friendly vacation rentals

Our top choices for a great stay

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West

The price is CA $2,000 per night from Dec 24 to Dec 25
CA $2,000
CA $3,327 total
Dec 24 - Dec 25
includes taxes & fees
Stay at this vacation home in Summerland Key. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Sugarloaf ...
9.8/10 Exceptional! (7 reviews)
Opens in a new windowThe Hemingway - Beach Houses Key West
Waterfront Beach Houses with Dock & Heated Pool!

Waterfront Beach Houses with Dock & Heated Pool!

Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and a garden. Popular attractions Big Pine Key Flea Market and Blue Hole are located ...
9.8/10 Exceptional! (59 reviews)
Opens in a new windowWaterfront Beach Houses with Dock & Heated Pool!
Tree Top Paradise

Tree Top Paradise

Book a stay at this family-friendly vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Florida Keys ...
9.8/10 Exceptional! (19 reviews)
Opens in a new windowTree Top Paradise
Florida Keys Beach Getaway

Florida Keys Beach Getaway

Stay at this vacation home in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Sugarloaf Beach ...
9.6/10 Exceptional! (27 reviews)
Opens in a new windowFlorida Keys Beach Getaway
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Blue Hole and Crab Key are located ...
9.6/10 Exceptional! (58 reviews)
Opens in a new windowTorchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Family Retreat Ocean front pool

Family Retreat Ocean front pool

Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
9.4/10 Exceptional! (77 reviews)
Opens in a new windowFamily Retreat Ocean front pool
The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!

The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!

Stay at this vacation home in Summerland Key. Enjoy laundry facilities, patios, and satellite TV channels. Popular attractions Florida Keys Beaches and Venture ...
9/10 Wonderful! (4 reviews)
Opens in a new windowThe Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

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

The price is CA $316 per night from Dec 6 to Dec 7
CA $316
CA $753 total
Dec 6 - Dec 7
includes taxes & fees
Stay at this vacation home in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Our guests praise the property condition in our ...
8.4/10 Very Good! (117 reviews)
Opens in a new windowJust 20 miles from Key West! Oceanfront, dockage, swimming pool
Beach Getaway in the Florida Keys

Beach Getaway in the Florida Keys

Stay at this vacation home in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Sugarloaf Beach ...
8.2/10 Very Good! (7 reviews)
Opens in a new windowBeach Getaway in the Florida Keys
**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…

**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…

Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Opens in a new window**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
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.