If someone asked you what area had the most expensive average house price in Florida, you’d probably guess someplace in Miami or Palm Beach. Actually, it is the little town of Boca Grande, located at the southern tip of Gasparilla Island. It has been famous as the top Tarpon fishery in the world for over a century, hosting numerous prestigious tournaments every year. Other than world class fishing, Boca Grande is known for being a place where many celebrities come to vacation. The small town offers privacy that you can’t find on many other islands, and high end accomodations that keep them coming back. There are variety of luxury Boca Grande vacation rentals, but also a surprising number of reasonably priced rentals that are still incredibly nice.

The beautiful accomodations and delicious restaurants come secondary to the one thing that keeps people coming back to Boca Grande. The beach. The beautiful stretch of sand on Gasparilla Island is one of the top beaches in South Florida. The crystal clear turquoise water looks much different than many areas of the Gulf, reminiscent more of a Caribbean beach than a Florida one. It’s easy to get here, Boca Grande is close to major airports in Fort Myers, Punta Gorda and Naples. Having options on where to fly into makes finding good flights easy. We hope this list of the best Boca Grande vacation rentals makes planning your trip a bit easier.

The 5 Highest Rated Boca Grande Vacation Rentals

5. Bird Key Retreat, A 5BR Luxury Boca Grande House Rental

Starting off our list is a house named Bird Key Retreat. This property is located on the calm bay side of Boca Grande. There is a private beautiful pool right off the (also private) white sand beach. At the edge of the beach there is a 39′ private deep water dock with a boat life that renters are free to use. Whether you bring your own boat or rent, this is an uncommon amenity for the area and a really cool part of the property. Between the pool, beach and dock there is a ton of options for keeping kids (or kids at heart) entertained.

This luxury Boca Grande house rental is rated to sleep 12 people. There are 5 total bedrooms, 1 of them being a bunk room with 4 beds (just something to be aware of). This rental is located at the very north end of the island, and it can be a bit of a hike getting back to downtown Boca Grande when traffic is busy. The trade off here is this end of the island is really quiet and laid back. If having access to a boat dock and private pool is something you are looking for in a Boca Grande beach house rental, then Bird Key Retreat just might be the house you are looking for. Average VRBO Review Score: 4.9/5.0 Check Rates and Availability: Bird Key Retreat House Rental on VRBO.com

4. Newly Renovated 2BR Boca Grande Condo Rental at the Boca Grande Club

The Boca Grande Club is a sprawling 60 acre private community on the Gulf side of Boca Grande. This high end complex includes clubhouses, pools, fitness centers and restaurants. The groups of small townhouses and condos are very spread out on this complex, which keeps it from ever feeling crowded. It reminds us a lot of South Seas on Captiva Island. Most of the condos in Boca Grande Club are 2 level, with 8 units per floor.

This beautiful Boca Grande condo rental was fully renovated a couple years ago and looks brand new. We love all the light airy decorations and color scheme of this property. The new high end appliances are a nice touch in the kitchen as well. The covered lanai with a west facing Gulf view is the perfect place to relax after a long day on the beach. The private sun deck off the lanai is equipped several loungers as well. The beach is 50 steps off the sun deck, making this property one of the closest to the beach in the Boca Grande Club. Many Boca Grande condo rentals on the island sit way back off the water and are advertised as being beachfront (keep an eye out for that). If the added amenities of Boca Grande Club interest you, this is without a doubt one of the best units in the complex. Average VRBO Review Score: 5.0/5.0 Check Rates and Availability: Boca Grande Club Condo Rental on VRBO.com

3. Brand New 5BR Luxury Boca Grande Beach House with a Huge Pool

This newly constructed Boca Grande house rental has not been available to rent for very long but has been getting rave reviews from guests. Everyone loves how private and quiet the property is. The house is located about 400 yards from the beach, recommend renting a golf cart to make that trip easy. You can then use your golf cart to get to the restaurants and shops in downton Boca Grande. The golf carts are completely legal to drive in Boca and are often used instead of cars.

This house rental has one of the largest private pools on the island, along with a large amount of deck and lounge space around the pool. The outdoor gas fireplace off the pool deck makes for a relaxing area to sip a glass of wine in the evening with a view of the famous Boca Grande Lighthouse. The kitchen is equipped with luxury Wolf ovens and Sub Zero refrigerators, perfect for a meal in with larger groups. The 5 bedrooms in this house are rated to sleep 10 comfortably, with the master overlooking the pool on the first floor. There are a variety of extras included in the garage, including a couple of cruiser bikes to explore the island. This is a great luxury Boca Grande rental for anyone who values privacy and an amazing pool. We put it at #3 because it is a bit pricey in our opinion compared to the property in our #1 spot. Nonetheless, it is still one of the top properties on the island. Average VRBO Review Score: 5.0/5.0 Check Rates and Availability: Brand New Luxury Boca Grande House Rental on VRBO.com

2. Gulf Dunes, a 2BR Beachfront Boca Grande Condo Rental

Gulf Dunes is a small beachfront condo complex on the southern end of Boca Grande. This area is ideally located close to restaurants and shops, convenient for both bikes and golf carts. This 2 bedroom, 3 bath Boca Grande condo rental currently is sitting at a perfect 5.0/5.0 on it’s reviews from past guests. It isn’t easy to accomplish this, and it proves how much pride the owner (Rob) takes in maintaining his property.

This condo isn’t over the top high end, but it doesn’t need to be. It is very nice, extremely clean, in a great area and one of the best values on the island. These units sit a bit farther off the beach, with only beautiful dune grass between the deck and the beach. This condo is the perfect setup for an adult couple with kids, but the twin beds in the second bedroom make it a little problematic for two couples. This Boca Grande vacation rental is a solid enough value that I doubt many will complain about the bed setup. If you are looking for the highest rated Boca Grande condo rental that is also a tremendous value, look no further. Average VRBO Review Score: 5.0/5.0 Check Rates and Availability: Gulf Dunes 2BR Boca Grande Condo Rental on VRBO.com

1. Boca Grande Palms, the Ultimate Luxury Private Estate on Gasparilla Island

Boca Grande Palms is one of the rare rentals that takes your breath away when you see it. There simply isn’t another Boca Grande rental property that can compete with the level of luxury and included amenities as this one. This definitely isn’t the modern styling that you would see in a new construction build, but rather the old world Tuscan style luxury that is timeless. The pool and outdoor spaces at Boca Grande Palms look like something pulled straight from a magazine. From the ivy covered walls to the magnificent pool shaded by mature palms, every part of this property is unparalleled.

One of the most shocking features of this Boca Grande estate rental is the price. We would expect it to be listed for much more per night than it rents for. This also means that it can be extremely difficult to book. Included in the rental price are 2 golf carts and 10 (!) bikes. This is probably close to $1000 in added value per week. If you want to make this rental truly all inclusive, that is an option as well. For an added fee you can have all meal prep, cleaning, butler service or any combination of these services. Boca Grande Palms is fully deserving of being the #1 Boca Grande vacation rental and we can’t recommend it enough. Average VRBO Review Score: 5.0/5.0 Check Rates and Availability: Boca Grande Palms Luxury Mansion Rental on VRBO.com