Vacation Rentals & House Rentals in Little Gasparilla Island

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Beautiful Waterfront Condo at Boca Grande North - A Serene, Happy Space!

Little Gasparilla Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$407

★ Secluded Holiday Retreat/ Island Paradise & Waterfront Condo ★

Little Gasparilla Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$319

**Upscale LGI Experience** Private Bayfront Condo

Little Gasparilla Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$344

Great rentals within 20 miles that match your search

Park Model with lanai, large deck, block from pool

Venice house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$121

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$212

Venice Florida Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$126

Coral Creek Landings Town Home-3 Bedroom-3 Bath

Placida townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$144

Haven Hideaway lives up to its name. Perfect holiday villa

Rotonda West villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$261

Superb Home Perfect Place, true description of this wonderful villa. Your

Rotonda West villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$261

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$155

Practically Perfect in Every Way a real dream home

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$119

The Bokeelia Boathouse, waterfront, Pine Island

Bokeelia bungalow

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$338

North Captiva Hidden Beach House with Private Pool

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Everything great about the beach with no crowds” My family loved this experience and will be back! The kids got a kick out of taking the golf cart around and looking for turtles. The house is great and has everything you could possibly need.

Price per night from

$487

6122

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$114

North Captiva Private Pool Home Shell Cottage

North Captiva Island house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$458

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$189

Different from others - your HIDEAWAY facing south

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$212

Fabulous private south facing villa with great golf course views

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$206

Littlelakelife

Port Charlotte house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$114

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$211

Great Beach Complex Home with Bikes, Kayak & More.

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$206

Large 4 Bedroom/2 Full +2 Half Bath

Placida house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$338

CAPE CORAL FLORIDA WATERFRONT HOME

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Awesome Home in Cape Coral” I would give this home more stars if I could. Gorgeous home, very clean and fully furnished. Scott (owner) is very responsive. Hoping to rent it again next winter. Ten thumbs up!!!

Price per night from

$328

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$229

Luxury Gorgeous Renovated Good Neighborhood 3 Bed

Port Charlotte bungalow

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$108

“Quiet Spacious Well Appointed Home” Central located in North Port in a quiet residential area between Naples and Sarasota with quick access to I -75 to allow easy access to many beaches, attractions and restaurants. The owner has thought of everything for a day out with the family at the beach including shell scoops to find that special seashell or prized shark tooth!! The house has a very well appointed kitchen, spacious pool area and a heated pool and hot tub. There is even a full office to keep up with any computer needs you may have. The Wifi is fast and efficient. Kurth we thank you for the use of your home and your hospitality even when you and your and family were on vacation overseas. We would recommend this property to any vacationer. Jerry and Claudette

Price per night from

$229

Waterfront with dock and heated pool

Punta Gorda house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$218

Casa Indulgence in Matlacha

Matlacha house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$802

Spacious Home Built in 2014, 30' Pool, Large Lanai

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$189

Super Location; BEAUTIFUL condo grounds

Port Charlotte condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$58

THE FANCY FISH..Enjoy Pool "Sandy Beach" Boat Lift

Matlacha house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“If you want an awesome getaway without having to leave the property for fun...this is your place!” This home has an awesome dock for fishing, boat lift, swimming pool, sandy beach with beach chairs, kayaks and completely fenced in property in case you want to bring your pet with you. The chef's kitchen is amazing with top of the line appliances for all of your meals that you will want to cook. You can walk to the shops and restaurants that are iconic to this area. A definite return for us!

Price per night from

$245

Lilsis by the Lake with 4 sleeps and heated pool

Port Charlotte house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Wonderful Florida Holiday” We enjoyed the month of March in the Lilsis home and it was wonderful. We found the house to be very clean, updated and comfortable - the exceptional weather made our time in the beautiful new pool very enjoyable. The neighborhood was quiet and walking and biking were a pleasure. The lake view, with it's wide variety of wildlife and the amazing sunsets, was an added bonus. Boris, and his team, were great hosts - very friendly and responsive. We are already looking forward to our 2016 visit.

Price per night from

$194

Chaves - 6 sleeps with heated pool

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Clean and comfortable environment” We truly enjoyed our stay at the Chaves house. It was meticulously clean and comfortable. The downside is that the cable was not working and netflix was offered on the ammenities page, but that too was not available. I would definately stay again!

Price per night from

$194

Addy by the Lake with 4 sleeps and heated pool

Port Charlotte house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Peace and Tranquility” Modestly furnished with everything you could possibly want. Super pool with great view over the lake and accompanying birdsong. Resident alligator and herons complete the picture.About 10 minutes drive to the Mall etc and around 20 mins to the beach/golf etc if that's what you want. A great place for that R&R.

Price per night from

$194

Van Nuys - 6 sleeps with heated pool

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$194

Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!

Don Pedro Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

Price per night from

$596

Viewing 38 of 309
rentals in Little Gasparilla Island

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About Little Gasparilla Island

The southernmost of three islands which includes Don Pedro and Palm Islands, Little Gasparilla Island is truly a tranquil paradise, and the perfect place to live out your desert island dream.

Why not find your perfect beachfront vacation rental by browsing FlipKey’s collection of Little Gasparilla Island properties?

About Little Gasparilla Island

The islands of Don Pedro, Palm Island and Little Gasparilla were once separate islands, until a hurricane in the 1960s closed the passes and destroyed the bridge from Little Gasparilla to Palm Island. Today, they are one island, and the bridge has never been rebuilt. There are no roads or cars on Little Gasparilla, giving it a lost-in-time atmosphere, accessible only by water taxi. 

It’s said that the island was initially settled by the notorious pirate Jose Gaspar, after whom it takes its name, and he was said to have built a palace at Boca Grande. Whether he existed or not, the island today has become a popular attraction for vacationers from the surrounding area.

Shop at the fish market in Placida on the mainland and bring your supplies across by water taxi.

What to do

With no stores or restaurants on the island, all that’s left to do is enjoy a thoroughly relaxing vacation. With 7 miles of pristine sand beaches, you can laze in the sun, go swimming or spot sea turtles, dolphins and manatees. Enjoy a charter fishing trip, rent a boat, or go shelling on the beach – you can even find plenty of prehistoric shark’s teeth here, and spot starfish, conchs and sand dollars. It’s not uncommon to find the beach completely empty, particularly outside of peak season, and bird watching for blue herons, osprey and white pelicans is a popular pastime.

Take a trip to Little Gasparilla Island State Park, or enjoy the 7.5 mile walk from the south tip of the island to the north tip of Palm Island, for a lovely way to spend a sunny afternoon.

Top Little Gasparilla Island travel tips

The nearest airports are Sarasota Airport, just over an hour to the north, and Fort Myers, an hour to the south.

There’s a restaurant at Palm Island Resort (with an extensive menu), but otherwise you’ll need to head to the mainland by water taxi for dinner (or cook at your vacation rental).

You can call for a water taxi to pick you up at the local marina on the mainland – just tell them your dock number and they’ll drop you directly at your vacation rental.

Step back in time with a vacation on Little Gasparilla Island – it’s the best way to escape it all, whether you’re enjoying a family vacation or a romantic retreat.

With over 300 villas and condos to choose from, you’re sure to find your perfect tropical island getaway with FlipKey!

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