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

$345

Great rentals within 20 miles that match your search

Pine Island Hideaway ~ competitive rates!

Bokeelia condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$131

Summertime Vacation Port Charlotte

Port Charlotte house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$104

Meehan - 6 sleeps, heated pool, down-town

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$194

Meehan - sleeps 6 with heated pool, downtown

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$178

Relax and Enjoy the sunset ath this waterfront gulf access saltwater canal

Punta Gorda house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

“Wonderful Family Vacation with No Worries” Thank you! Our stay was lovely. The owners returned our phone calls, and were very willing to help if there was a need. The home was larger than the pictures depicted. We would love to return.

Price per night from

$574

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

Beautiful and completely remodeled cottage retreat minutes from the beach!!

Englewood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$144

Price per night from

$230

Peaceful, Private, Paradise in Englewood. House with heated pool

Englewood house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$259

Second Star

North Captiva Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$660

Seaside Vacation Home w/office

South Venice house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$211

Englewood’s Paradise Home

Englewood house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$144

Waterfront living in Punta Gorda Isles w/Amaizng sunset views from the pool!

Punta Gorda house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent vacation” Nicest owner I've ever dealt with house better then expected already booking for may amazing time and caught four fish including a sting ray thanks again John cox

Price per night from

$459

Tranquil villa in the heart of Englewood, close to Beaches

Englewood villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Wonderful location and owner is super friendly” Amazing condo very well maintained. Great location to the beach and stores only min. away. We'll visit again!

Price per night from

$207

Rentalvilla-florida villa H

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$172

Florida Golf Vacation Villa

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$339

Really stunning home, perfect position, south facing overlooking the river

Cape Haze villa

  • 4 bedrooms
  • 8 bathrooms
  • sleeps 8

Price per night from

$169

Responds fast! avg. 2 hours 46 minutes

Price per night from

$153

Beach Villa Paradise

Englewood villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$172

Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$1,148

Punta Gorda Beach Escape

Port Charlotte villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$114

Price per night from

$230

New Modern Waterfront Home

Port Charlotte house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$316

Million Dollar View in PGI

Punta Gorda condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 6 minutes

Price per night from

$144

Gulf to Bay Coop

Manasota Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$75

2/2 POND FRONT, ONLY 10 MINS FROM ENGLEWOOD BEACH

Englewood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$127

Price per night from

$115

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$276

Venice Pool Home

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$224

Stunning BRAND NEW 3 bed home, fabulous pool overlooking river,

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$319

Come to Manasota Key this fall. It’s the place to be!

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$459

Price per night from

$482

A little piece of paradise: Villa Santorini on the Lake

Rotonda West villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$195

Villa Paradise Waterfront Gulf Access

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$205

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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