Discover a selection of 72 vacation rentals in Gasparilla Island, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $284 per night, and houses and villas are popular options for a stay in Gasparilla Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Gasparilla Island
Destination guide

Testing the waters in Boca Grande

Hop in your Delorean and tune up your flux capacitor – Boca Grande is a land outside of time, known for its fishing, charming downtown, and wealth of sandy beaches along Florida’s gulf coast. Set on Gasparilla Island, the historic village is light years away from the hustle and bustle of modern life, and you’ll find plenty of waterfront trails, bike paths, and state parks. With a Boca Grande vacation rental, you’ll be close to the area’s biggest attractions, like Gasparilla Island State Park, Boca Grande Beach, and the Boca Grande Historical Society and Museum.

Things to do

Ancient (and not-so ancient) history in Boca Grande

Want to become an expert on all things Boca Grande? Then check out the seasonal Boca Grande Historical Society, where you can find information about the town’s past, from its earliest settlers to the present day. To really round out your knowledge, you can also head to the Port Boca Grande Lighthouse Museum. Set in a 19th-century lighthouse, the museum is home to environmental and historical exhibits, and the interactive “please touch” area is always a hit with families. The site also hosts regular events and outdoor excursions in the surrounding state park.


Boca Grande – and the sand played on

First up: time to hit the beach. While the island has a wealth of coastline, the beach at Gasparilla Island State Park is popular with families thanks to its broad, sandy shore and mild current. Boating’s popular here – it’s also the only way to get to Cayo Costa State Park, a scenic island where you can spot dolphin, manatee, and plenty of shorebirds. Closer to town, the Boca Grande Bike Path is a great way to explore the island, offering more than 6 miles of cycling trails along a former railway line.


Sun, sand and swimming all year 'round

Thanks to an annual average temperate of 75 degrees, it's likely you can take a dip no matter the season. While the mercury does drop a bit in December and January, calm tropical breezes still might make for perfect beach days. June through September can be fairly rainy, but you can look at this as nature's way of cooling off those humid summer days. The best advice is to pack light, but with an extra layer or two for snuggling up in your Gasparilla Island vacation rental on those cool winter nights or rainy summer evenings.

Natural features

Boca Grande – friends in low places

Boca Grande sits beside the Gulf of Mexico on the western coast of low-lying Gasparilla Island. It’s surrounded by broad, sandy beaches, marshy wetland, and coastal inlets, and the surrounding waters are dotted with pristine islands that offer countless opportunities to spot local wildlife. Dolphins and manatees are regular sights, and the Boca Grande State Park is home to tortoises, bald eagles, and American oystercatchers. With a Boca Grande vacation rental, some of the country’s most unique and diverse ecosystems will be just outside your door.

What are the top vacation rentals in or near Gasparilla Island?

Whether you're looking for an intimate retreat for you and your boo or a sprawling house to fit the family, you'll find some top vacation rentals in and around Gasparilla Island. Here are a couple we think you'll like:

  • "Beautiful Villa Lake View Heated Pool" is a hit with guests. Around 20 miles from Gasparilla Island, it has 3 bedrooms and plenty of amenities to help you feel at home, including a fridge and a nearby beach.
  • Alternatively, unpack your suitcase at "Gulf Front Sanibel Rental Recently Renovated". Located around 25 miles from the heart of Gasparilla Island, it has 2 bedrooms and comes with a smart TV and nearby ecotour services.

For even more great options, use the search bar at the top of the page to find the perfect Gasparilla Island vacation rental for you.

What are the best tiny house vacation rentals in or near Gasparilla Island?

You need only set foot into one of our tiny house vacation rentals in Gasparilla Island to figure out that cool things really do come in tiny packages. Smartly designed to maximize every spare inch of space, these pint-sized pads deliver a big vacation experience:

  • Leave it all behind and escape to "Hobbit House, Tiny Home". This getaway in Jacarandas packs plenty of comforts into its cozy space, such as internet services and a heated pool.
  • "New Tiny House - Introductory Price Minutes From Sanibel And Fort Myers Beach" in Iona is another highly rated option. A toaster and coffee and tea making facilities will help make your stay here even more cozy and comfortable.

What are the top-rated vacation rentals for weekend getaways in or near Gasparilla Island?

At Vrbo, we think weekends were made for fun. Stay in one of these weekend getaways in and near Gasparilla Island and make the most of all the awesome things to do close by:

  • "5 Star, Pet Friendly, Sunny, Private Old Florida Charm Cottage And Mins To Beach" is a comfortable option around 25 miles southeast of the center of Gasparilla Island. There's no need to go far to find something to keep you occupied around this property. Get outdoors and discover Otter Creek Golf Course and Eagle Ridge Golf Club. Activities like sailing and windsurfing will perfectly round off your whirlwind break.
  • Alternatively, enjoy a more leisurely pace of life at "Historic 1911 Cottage With Pool". Approximately 1 mile south of Gasparilla Island, activities around here include kayaking and snorkeling. Prefer sightseeing? Plan an excursion to Charlotte Harbor Preserve State Park and Cape Coral Historical Museum.

Can I find studio apartments for rent in and around Gasparilla Island?

Studio apartments are a tough act to follow when it comes to location and convenience. Take a look at these studio apartments for rent in or near Gasparilla Island and immerse yourself in the local vibe and energy:

  • Put your bags down and your feet up at "July Special, Luxury, Gulf View". Amenities including an ocean view and a fridge will make you feel right at home here.
  • "Wow 121/n - Spec. Season - 7 Nights. Cozy Beachside Unit" is another great choice. Make yourself at home and take advantage of a phone, off-street parking options and more.

When you're ready to step outside your studio apartment and sightsee, there's loads to keep you occupied around Gasparilla Island. Into art and culture? Swing by Sidney & Berne Davis Art Center and Alliance for the Arts.

Can I find short term rentals in or near Gasparilla Island?

Locating a short-term rental in and around Gasparilla Island won't be a problem if you only have a few nights free. Whether you'd like a one-bedroom apartment for one or a house that'll fit your family, you'll find a place to suit on Vrbo. Here are a handful of our favorites:

  • Reserve a few nights at "4 - Bedroom / 2 - Bathroom / Tiki Hut On The Water" in central Gasparilla Island. Here, you'll have easy access to attractions like Edison and Ford Winter Estates.
  • Also not far from the center, "To Infinity And The Beautiful Beyond" is another fantastic option. Looking for a bit of sightseeing inspiration during your stay? Sun Splash Water Park is a good start.

What are the best romantic weekend getaways in or near Gasparilla Island?

Nothing says "I love you" like a romantic weekend trip. If you want to spend a couple of relaxing nights away with your partner, we've got some romantic getaways in and around Gasparilla Island that will set your heart aflutter:

  • Sneak away on Friday afternoon for a couple of passion-filled nights at "Beautiful Villa Lake View Heated Pool". Located approximately 20 miles from Gasparilla Island, this place comes with lots of nice touches, including a nearby bay and beauty services.
  • Otherwise, spend a few days drinking wine and canoodling at "Gulf Front Sanibel Rental Recently Renovated", around 25 miles from Gasparilla Island. Beauty services and a swimming pool will help set the mood.

Are there mansions for rent in or near Gasparilla Island?

Nothing says "Best. Vacation. Evvv-er." like staying in a mansion. Treat your nearest and dearest to an unforgettable escape at one of these mansions for rent in or near Gasparilla Island:

  • Character, charm and style — "Quaint Mansion In Aquitaine Estate With Private Garden" has it all. Around 25 miles southeast of Gasparilla Island and offering a swimming pool and golf, this place is hard to top.
  • Another quality option is "Villa Sunset Cove - Spectacular Mansion Overlooking The Spreader Waterway". Around 20 miles to the southeast of Gasparilla Island, this fancy vacation rental is the crème-de-la-crème of homes and offers a swimming pool, beauty services and more.

What are the best large group vacation rentals in or near Gasparilla Island?

Vacation with others and have even more fun. Whether you're organizing an active escape with friends or a big family get-together, you'll have your pick of large group vacation rentals in and around Gasparilla Island:

  • Providing space, privacy and comfort, you'll get everyone's tick of approval at "6 Bedroom, 5 Bath Pool Home With - 2 - 110' Tv's 1 At Pool And 1 In Livingroom". Up to 14 people can be accommodated at this property which has 6 bedrooms, a garden and a swimming pool. This group getaway is around 30 miles to the southeast of Gasparilla Island.
  • Invite as many as 18 of your dearest friends to "1 Minute To Beach, Luxury Pool Home" and fill its spaces with laughter and love. This popular option has 7 bedrooms and is around 12 miles to the south of central Gasparilla Island. It's packed with features to keep your large group comfortable, such as a swimming pool and a garden.

What are the best houses for rent with a pool in or near Gasparilla Island?

From boisterous games of freeze tag to peaceful morning dips, a pool promises hours of fun for both adults and kids. Score some serious brownie points with friends or family by choosing a house with a swimming space in or near Gasparilla Island:

  • Make every day a pool day at "140 Primo Dr Waterfront House, Htd Pool". A nearby bay and pet-friendly facilities are a few of the other amenities that help make this place a favorite.
  • Another top-rated option is "Rockstar Beach House North Captiva Island - Accessible By Ferry Boat Only". There's a lot to love about this property besides its pool, such as outdoor furniture and a barbecue grill.

What are the best large family vacation rentals in or near Gasparilla Island?

Every catch-up with the family should be memorable. Whether you're organizing a break with the kids or a party with relatives, our large family vacation rentals in or near Gasparilla Island offer a home away from home with ample space for everyone:

  • Get everyone together at "4 - Bedroom / 2 - Bathroom / Tiki Hut On The Water", which has 4 bedrooms sleeping up to 10 guests. This retreat is located 25 miles to the southeast of Gasparilla Island and comes with amenities such as childrens activities and a kitchen.
  • "To Infinity And The Beautiful Beyond" also has the space you need to reconnect with loved ones. This rental is around 25 miles to the southeast of central Gasparilla Island and accommodates 8 guests in its 4 bedrooms. Cable/satellite TV services and a kitchen will help keep everyone content and comfortable.

If you want to do some sightseeing, there are loads of family-friendly attractions nearby to put on your to-do list. Sun Splash Water Park, Fishing Pier Fort Myers Beach and Jungle Golf Ft. Myers are excellent places to start.