Monthly Rentals in Gasparilla Island

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Cottage in Boca Grande
4.83 out of 5 average rating, 106 reviews

Charming beach cottage house with pool.

JosephRating, 5 stars3 months ago
This was the perfect place on Boca Grande for our family. A short walk from the beach and a quick gold cart ride to downtown. The cottage was very clean and having the pool access was a huge plus.
Guest favourite
Villa in Boca Grande
4.9 out of 5 average rating, 31 reviews

Luxury Retreats at Boca Grande - Boca Bay Watch

ErikRating, 5 stars1 week ago
We really enjoyed our stay and will definitely be back! This is a great location, especially for boaters. The pool was great. The sunrise views and watching the boats come and go were incredible. You’re walking distance from the beach and some great restaurants (i.e. Temptations, Scarpa’s, The Outlet, Pink Elephant, etc.). The pool was great, especially for entertaining the kids. The house was incredible and the host was very responsive and accommodating. I highly recommend renting a golf cart from Kappy’s (host recommendation) to putz around town and explore the area.
Guest favourite
Flat in Boca Grande
4.92 out of 5 average rating, 173 reviews

2 Bedroom Flat: Downtown Boca Grande:#1

TimothyRating, 5 stars3 weeks ago
Easy and clean - nice to be downtown - we enjoyed Boca Flats
Superhost
Apartment in Rotonda West
4.83 out of 5 average rating, 6 reviews

Rotonda Condo w/Pool, 2BD 2BA Near Beaches Monthly

HollyRating, 5 stars5 months ago
This condo had everything we needed and more! When we walked in, everything was so nice and clean. It is so tastefully decorated. The natural lighting is wonderful. It had everything there that we needed and everything had a place. The location is great! It’s easy to get to and not far from all the places we wanted to go. The condo is located in a nice quiet area. I loved having close parking. My kids loved the heated pool as well. They even included beach towels for us to use. We enjoyed visiting the local beaches and looking for sharks teeth. Thanks for including a rake for us to use to find so many! What a wonderful addition! The washer and dryer also came in super handy for us. The beds and pillows were very comfortable. We also appreciated the nice plush bath towels. We even had fun things to do when we chose to stay in. There were fun boards games, puzzles, and even books to read. I would highly recommend this place to anyone! Thanks for a great stay!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

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*Some exclusions may apply in certain geographies and for some properties.