Cutthroat Harbor Estates Rentals By Owner

There are a lot of options in Cutthroat Harbor Estates. If you plan on staying in the Cutthroat Harbor Estates area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Cutthroat Harbor Estates:

• Luxury * Panoramic Oceanfront Views * Boat Dock * Heated Pool
• Luxury 4BR Cudjoe Key Retreat | Swim Spa, Dockage & Boater's Paradise
• Escape to an oceanfront Home with Boat Dock + pickleball, Pool and more!
• Tropical Island Getaway - Venture Out Unit 196
• Tropical paradise on open water 35 ft seawall in beautiful Venture Out Community
• Waterfront Keys Sunset Spectacular
• Luxury Dream Home in the Fabulous Florida Keys!
• 20 miles from Key West! Large family-sized home with pool and BBQ area.
• Waterfront Retreat: Bikes, Paddle-boards, and Fishing Amenities Included
• Beautiful 2/2 with a 60 foot seawall 100 yards from Cudjoe Bay

There are many large, family-friendly vacation homes available in Cutthroat Harbor Estates; however, here are the most popular family rentals listed on our site:

• Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
• Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
• Special Rate Available April 2026 book now
• *CAREFREE ON CUDJOE @ THE BAY* Waterfront Home & Pool + LAST KEY SERVICES…

Yes, there are 34 self-catering vacation homes in Cutthroat Harbor Estates that have hot tubs, swimming pools, & other amenities.

There are more than 34 luxury villas and vacation homes in or near Cutthroat Harbor Estates. Filter by price to compare find the most expensive places to stay on Hottubhomes.

Yes, there are 34 pet friendly vacation homes and places to stays that are available in or near Cutthroat Harbor Estates that you may consider.