Vacation Rentals & House Rentals in Little Gasparilla Island

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309 house rentals

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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

$343

Great rentals within 20 miles that match your search

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

Cape Haze villa

  • 4 bedrooms
  • 8 bathrooms
  • sleeps 8

Price per night from

$168

Responds fast! avg. 2 hours 46 minutes

Price per night from

$152

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

$1,142

Punta Gorda Beach Escape

Port Charlotte villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$113

Price per night from

$229

Million Dollar View in PGI

Punta Gorda condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 6 minutes

Price per night from

$143

A little piece of paradise: Villa Santorini on the Lake

Rotonda West villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$194

Villa Paradise Waterfront Gulf Access

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$204

Gorgeous Awesome waterview Burnt Store Marina Punta Gorda Watch manatee play

Punta Gorda condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$206

Gulf to Bay Coop

Manasota Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$75

Florida Golf Vacation Villa

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$337

Burnt Store Marina Main Floor 2 Bedroom 2 Bath Condo

Punta Gorda condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$143

Almost Heaven

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$286

Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip

North Captiva Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$570

Venice Pool Home

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$223

Beautiful direct access waterfront home in Matlacha Isles

Matlacha house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$257

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

Rotonda West villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$318

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

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$457

Venice Pool Home Centrally Located, Just Waiting For You

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$274

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

Englewood house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$126

Price per night from

$115

Island Attitude 2/2 beach condo

Manasota Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$314

Price per night from

$506

The Preserve at Charlotte Harbor

Punta Gorda apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$172

Gorgeous 2nd story 2B condo with vaulted ceiling & leather furniture

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Port Charlotte Retreat

Port Charlotte house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 10 minutes

Price per night from

$115

Vacation Rental Boutique Suite Windmills

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$223

Vacation Rental Boutique Suite Amsterdam Canals

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$223

Vacation Rental Boutique Suite Bicycles

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$246

Vacation Rental Boutique Suite The Bridge

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$246

Vacation Rental Boutique Suite Tulip Fields

Englewood private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$246

HOUSE NEAR EVERYWHERE

Port Charlotte house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 10 minutes

Price per night from

$143

Safe, Quiet & Peaceful home in great neighborhood

North Port house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$216

Dream villa in a quiet location with private pool, private beach and Wi-Fi

South Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$343

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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