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Vacation Rentals & House Rentals in Little Gasparilla Island

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672 house rentals

Relaxing Private Island House (LGI)

Little Gasparilla Island house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$196

Lucky Me ! A Waterfont Retreat

Little Gasparilla Island house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$315

BELLISSIMA BY THE BEACH

Little Gasparilla Island cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 35 minutes

Price per night from

$487

Brand new double-storied round hurricane-proof house, 3000 sq ft with sea views

Little Gasparilla Island house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$413

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

Little Gasparilla Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 43 minutes

Price per night from

$410

★ Secluded Holiday Retreat/ Island Paradise & Waterfront Condo ★

Little Gasparilla Island condo

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$261

Great rentals within 20 miles that match your search

IT`S A BEAUTIFUL DAY IN PORT CHARLOTTE FLORIDA!!!

El Jobean house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$258

Beautiful 2 Bed / 1 Bath w/Pool on Golf Course

Rotonda West house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$194

Park Model with lanai, large deck, block from pool

Venice house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$136

Practically Perfect in Every Way a real dream home

Rotonda West villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 54 minutes

Price per night from

$135

Mini Mansion/Home Away from Home

North Port house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$246

2BR Steps to Gulf-Manasota Key, Modern Clean Condo

Englewood apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Paradise” The first time we stayed in Englewood, we loved it so much we have been coming back ever since. This condo is clean and steps to the beach. Quiet area with so much to do. Dan is always accommodating to any of your needs. Also walking distance to restaurants.

Price per night from

$51

Super Location; BEAUTIFUL condo grounds

Port Charlotte condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$65

2/2 FURNISHED CONDO ROTONDA WEST

Rotonda West condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$193

It's Not Too Late! 2B/2B Condo available for season at the Plantation G & CC

Venice condo

2 bedrooms / 2 bathrooms / sleeps 3

Price per night from

$130

keylimevilla

Matlacha house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$99

Punta Gorda/Port Charlotte Cozy Living

Punta Gorda house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$52

Santana Family H-3 unit at Hideaway Bay Beach Club

Placida condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

Stunning property in quiet sort after location

Rotonda West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$189

Warm Mineral Spring Vacation Home

Warm Mineral Springs house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$90

Million Dollar View in PGI

Punta Gorda condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$118

6122

Englewood house

3 bedrooms / 6 bathrooms / sleeps 8

Responds fast! avg. 26 minutes

Price per night from

$104

Beautiful Rotonda Villa, South Facing, Canal Views

Rotonda West villa

3 bedrooms / 3 bathrooms / sleeps 8

“yes” best place ever Great place not far from the beach and shops and bars ,you see wildlife lot of wildlife villa is so stylish

Price per night from

$148

Lovely, relaxing home in Rotonda West , Florida

Rotonda West villa

3 bedrooms / 2 bathrooms / sleeps 6

“Great rental!” Great vacation rental. Can’t say enough good things about the home, pool area and the extent to which the owners make sure there is everything you need to enjoy your stay there! I have never stayed in a rental that even came close to this one in respect to how well it was stocked with everyday necessities. Enjoyed our week away from this Michigan winter!

Price per night from

$128

Tropical Gardens and Golfer's Heaven

Rotonda West house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

Price per night from

$145

Large Island Home w/ Heated Pool Private Beach Access & Tropical Beach Bar/Grill

North Captiva Island house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 30 minutes

Price per night from

$919

LAST MINUTE SPECIALS! BEACH FRONT HOME - Private & Perfect, Paradise Awaits!

North Captiva Island house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 30 minutes

Price per night from

$804

Gorgeous Furnished Pool Home in Desirable Venetia!

South Venice house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$107

Comfortable and Spacious Three Bedroom With Private Pool

Rotonda West villa

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 49 minutes

Price per night from

$123

The Preserve at Charlotte Harbor

Punta Gorda apartment

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$172

Luxury Venice Florida 4 Bedroom home with Pool

Venice villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 34 minutes

Price per night from

$285

Luxury Venice, Florida Gulf Coast Condo

Venice apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 27 minutes

Price per night from

$91

Welcome to Paradise

Venice house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$171

Charming Costal Retreat

Venice apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$124

Twin Palms Sleeps 12, Ideal for 2 Families!

Port Charlotte house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 8 minutes

Price per night from

$93

Mermaid House beach apartment on first floor , No steps 1 bedroom sleeps 4-5

Englewood house

4 bedrooms / 1 bathroom / sleeps 4

“Great winter vacation place” My husband, our Jack Russell terrier Sally Mai, and I had a wonderful two weeks in the Captains Quarters. Darlene is a pleasure to work with. The beach was great, there are wonderful restaurants and we had a very relaxing time. We are certainly planning to return.

Price per night from

$335

THE MERMAID HOUSE

Manasota Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$558

Viewing 37 of 672
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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