Key2TheSea

2-Bedroom, 2 Bath

King, 2 twins, sleeps 4

This charming tropical treehouse sits amidst the treetops on Jolly Roger Trail near the south end of Little Gasparilla Island. Little Gasparilla is a bridgeless barrier island so plan to leave your car and your cares on the mainland and step into a beautiful tropical environment.

The home offers plenty of room for everyone to spread out, with spacious bedrooms that open to the screened porch and a large air conditioned living area. The master bedroom on its own side of the house has an en-suite bath with shower and a private deck opening to the private back yard. The bedroom has a king bed and French doors that open to the screened porch. The second bedroom offers two twin beds and also has French doors that open to the porch.

The kitchen has seating for 4 on the kitchen island, and has stainless appliances and all the dishes and cookware you need.

The front porch extends the width of the house and nearly doubles the living area of the house. It is spacious and breezy, and very private. You may glimpse a golf cart pass by on Jolly Roger Trail, but this house is nestled in the treetops for lots of peace, quiet and privacy.

Free kayaks are available if you wish to explore the bay. The owner also includes beach towels and beach chairs for their guests' use. We may also be able to offer golf cart rental with this property, subject to availability.

There is a covered back porch at the back of the house with views of the treetops. It makes a lovely spot from which to have morning coffee. There is another open porch off the master bedroom perfect for private sunbathing or relaxing in the sunshine on a January day.

The best feature of this home is the peace and privacy it affords. Set back from the road, on a quiet seldom-traveled pathway, Key2TheSea offers a great spot for a peaceful quiet vacation with the beautiful beaches and great fishing of Little Gasparilla just a short stroll away. The beautiful beach is about a 5-7 minute walk from the house.

Rents from $275/night or $1925/week, 3 night minimum

Please be aware that we can not permit guests to check in or check out the same day another guest will be occupying the property. We require at least 24 hours of vacancy between each guest.

  • WiFi - Starlink

  • Pet Policy - permitted with $100 pet fee (per pet). The following breeds are NOT permitted: Akita, American Bull Dog, Beaucerons, Caucasian Mountain Dog, Chow Chow, Doberman Pinchers, German Shepherds, Great Danes, Keeshounds, Pit Bull, Staffordshire Terriers, Presa Canarios or Rottweilers.

  • Cleaning Fee - minimum $265 cleaning fee

  • Vacation Rental Damage Protection - $59 fee for “all risk” damage protection through Waivo

  • Minimum Renter Age - 25

  • Easement Dock - dock 78 or 79 -first come first serve, no boats greater than 24 feet (boat + motor), requires parking placard and spring ties.

  • Water Taxi Drop Off- dock 75

  • TV - wifi enabled

  • Grill Type - charcoal

  • Coffee Maker- drip (filters provided)

  • Parking - $8/night ($10/night if you have a boat trailer) at Eldred's Marina where you meet the boat taxi

  • Holiday surcharges: applied for reservations for Independence Day, Thanksgiving, Memorial Day, Labor Day, and Christmas/New Years timeframes. PLEASE NOTE THAT MINIMUM NIGHTLY STAYS MAY BE INCREASED FOR THESE DATES AS WELL.

  • Early check-in/Late check-out -Check in is 4pm, Check out is 10 am. Early check in or Late check out may be available for an extra charge. Ask the booking manager for details

Recent Reviews

We loved our stay on the island, it was so quiet and peaceful. The concierge was very helpful and easy to schedule, the house was very well stocked with towels and kitchen utensils. Terry the host was very quick to reply and provided top notch customer service. We thought all the beds were very thin and hard but everything else provided an excellent island getaway. Stacie B. Thanks Stacie- the beds have been replaced!

Close to the beach, great screened in porch, amazing property managers. Quiet and a great place to chill. Linda M.

My wife and I had an absolute blast on our vacation from the help getting to the house to setting up the dock for out boat, that was a close walk. This is our second trip to the Island. We will be back! I would go now but its an 11 hour drive. We have already started looking at places for next year. The people at Gasparilla Island Vacation Rentals are just awesome. I was searching for charcoal for the grill, and I reached out to see if Eldreds Marina had some they told me to hang on and they would bring it to my door. Wow, that’s over and above service. - Jack M.