Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL

Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...

9/10 Wonderful! (174 reviews)

"This location was perfect for what my husband and I needed. We brought our boat and were able to use the dock throughout our stay. We did have an issue with the AC system and Jennifer was great by putting us into another one of their units overnight until our units AC was fixed the next day. This ..."

Reviewed on 24 Jul 2026

Get rates

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cudjoe Key FL

Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...

Get rates

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key FL

Stay at this cottage in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are located ...

Get rates

See all 1,791 properties in Cudjoe Key

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.

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Cudjoe FL

Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and tennis courts. Our guests praise the helpful staff in their reviews. Popular ...

9.8/10 Exceptional! (259 reviews)

"The house was clean with plenty of room for everyone."

Reviewed on 7 Sept 2026

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL

Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...

9/10 Wonderful! (174 reviews)

"This location was perfect for what my husband and I needed. We brought our boat and were able to use the dock throughout our stay. We did have an issue with the AC system and Jennifer was great by putting us into another one of their units overnight until our units AC was fixed the next day. This ..."

Reviewed on 24 Jul 2026

Springs Venture Out Dolphin House #386 with beautiful open water views

Cudjoe Key FL

Enjoy free Wi-Fi, parking (surcharge) and laundry facilities. Popular attractions Florida Keys Beaches and Venture Key are located nearby.

9.4/10 Exceptional! (121 reviews)

"A/C was ice cold. Anytime we needed anything the hot was easy to get a hold of."

Reviewed on 26 Aug 2026

See all properties in Cudjoe Key

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.