Vacation Rentals & House Rentals in Little Gasparilla Island

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959 house rentals

(2) Very Good 

24

BEACHFRONT | Beautiful | Relaxing Views of the Gulf | Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$208

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$208

(5) Excellent 

28

Relaxing Private Island House (LGI)

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$171

Price per night from

$171

16

Sea Star Beach House: Sunsets Galore!

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$314

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$314

(19) Excellent 

Certificate of Excellence

38

Gulf Front Beach Condo (Little Gasparilla Island)

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island condo

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“LGI Spring Break 2018” LGI is an amazing place and my family enjoyed every minute of our time there. Pam was a very gracious and attentive host who was great to work with. We have already begun thinking about a return trip to the island and would not
…see more

Certificate of Excellence

Price per night from

$200

Price per night from

$200

(2) Very Good 

24

Island Home Retreat PRIVATE DOCK Free Kayaks Free Wi-Fi

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$195

Responds fast!
avg. 3 hours 19 minutes

Price per night from

$195

(10) Very Good 

46

Coconut Hideaway: Gulf-Front Dream House!

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“The island get away that so many resorts promise you...but this” I've been here a few different times, and I'm always sad to leave. It is the island get away that so many resorts promise you...but this is the real thing! The beach is very secluded, an
…see more

Price per night from

$314

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$314

(2) Excellent 

42

Lucky Me ! A Waterfont Retreat

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$230

Responds fast!
avg. 3 hours 46 minutes

Price per night from

$230

(2) Very Good 

38

"The Round House" - An Island Original!

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$320

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$320

(13) Excellent 

33

Hibiscus House - Beachfront Bliss on the Gulf!

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island cottage

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Tom Sawyer for one month” This was the first time we have ever done this kind of vacation--one month on an island. It was terrific!! Ran on the beach with our dog; great ocean (I know its the Gulf); very friendly folks; great fishing and a tremendous
…see more

Price per night from

$400

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$400

14

LaTeDa Beach House

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$314

Price per night from

$314

(1) Excellent 

25

Coconut Palm Cottage - Tropical Beach Getaway

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$200

(2) Average 

22

Serenity Cottage on Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$200

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$200

20

Island Dream House

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$298

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$298

(1) Excellent 

22

RoseMary's Beach House: Beachfront Elegance

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$276

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$276

21

Angler's Paradise - A Fisherman's Dream!

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$199

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$199

20

Island paradise Little Gasparilla island

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island condo

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$145

Price per night from

$145

13

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

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island condo

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$300

Price per night from

$300

26

★ Secluded Holiday Retreat/ Island Paradise & Waterfront Condo ★

Southwest Gulf Coast / Little Gasparilla Island

Little Gasparilla Island condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$178

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$178

Great rentals within 20 miles that match your search

Distance approx 18.33 km from Little Gasparilla Island

(4) Excellent 

34

Luxury Venice Home with (heated) Private Pool and Lake View

Southwest Gulf Coast / Venice

Venice house

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“I wish I was there right now :) !!!” My family and I had a wonderful time while at this beautiful, brand new, and completely furnished home. This was our first vacation since our daughter was born, and this place was the perfect retreat for the entir
…see more

Price per night from

$193

Price per night from

$193

Distance approx 5.5 km from Little Gasparilla Island

(22) Excellent 

32

"Old Florida Style" Villa + Heated Pool & Spa

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“amazing” Stayed for 2 weeks in early may fantastic villa superb location .The villa is home from home clean modern etc recommend this villa everytime..looking to go back very soon..just love it
…see more

Price per night from

$120

Price per night from

$120

Distance approx 16.67 km from Little Gasparilla Island

37

Park Model with lanai, large deck, block from pool

Southwest Gulf Coast / Venice

Venice house

1 3 90 nights min

  • 1 bedroom
  • sleeps 3
  • 90 nights min
  • Child Friendly

Price per night from

$104

Price per night from

$104

Distance approx 17.01 km from Little Gasparilla Island

37

ISLAND PARADISE

Southwest Gulf Coast / North Captiva Island

North Captiva Island house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$705

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$705

Distance approx 17.51 km from Little Gasparilla Island

(2) Average 

12

Boaters Paradise,5bedrooms 3 bathrooms, Private Pool

Florida / Bokeelia

Bokeelia house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$188

Responds fast!
avg. 3 hours 2 minutes

Price per night from

$188

Distance approx 15.77 km from Little Gasparilla Island

(3) Excellent 

50

Amazing Dream Villa with Saltwater Pool & Spa

Southwest Gulf Coast / Punta Gorda

Punta Gorda house

4 13 min stay varies

  • 4 bedrooms
  • sleeps 13
  • min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child Friendly

Price per night from

$666

Price per night from

$666

Distance approx 18.75 km from Little Gasparilla Island

14

Nw Cape Gulf Access Home With Heated Pool

Southwest Gulf Coast / Cape Coral

Cape Coral house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$198

Price per night from

$198

Distance approx 3.61 km from Little Gasparilla Island

(16) Excellent 

42

#15 luxury villa 3 bed 4 bath salt water pool sleeps 6

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
“Great value, great service, lovely villa” 6 of us stayed here for 2 weeks. The villa is excellent with everything you could want for your holiday (e.g. bikes, beach chairs, lilos together with computer, coffee percolator, ice-dispenser fridge etc. etc
…see more

Price per night from

$208

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$208

Distance approx 19.4 km from Little Gasparilla Island

10

Manufactured Home in scenic park

Southwest Gulf Coast / Punta Gorda

Punta Gorda house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$57

Responds fast!
avg. 56 minutes

Price per night from

$57

Distance approx 11.33 km from Little Gasparilla Island

(3) Excellent 

24

Secluded Home on Pristine Tropical Island

Southwest Gulf Coast / Boca Grande

Boca Grande house

3 9 1 night min

  • 3 bedrooms
  • sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.15 mi
  • Child Friendly

Price per night from

$331

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$331

Distance approx 16.37 km from Little Gasparilla Island

(1) Excellent 

7

Punta Villa Cottages - Historic District

Southwest Gulf Coast / Punta Gorda

Punta Gorda cottage

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 45 mi
  • Air conditioning
  • Pet Friendly

Price per night from

$67

Price per night from

$67

Distance approx 5.23 km from Little Gasparilla Island

14

Cozy, very affordable, 3 beds, 2 baths, solar or optional electrically heated po

Southwest Gulf Coast / Rotonda West

Rotonda West house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$112

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$112

Distance approx 15.48 km from Little Gasparilla Island

(1) Excellent 

10

Canal Front w/HEATED POOL by Fisherman's Village

Southwest Gulf Coast / Punta Gorda

Punta Gorda house

3 7 6 nights min

  • 3 bedrooms
  • sleeps 7
  • 6 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$247

Responds fast!
avg. 1 hour 5 minutes

Price per night from

$247

Distance approx 19.16 km from Little Gasparilla Island

10

Relaxing location, 3BD townhome, North Port, FL

Florida / North Port

North Port house

3 8 60 nights min

  • 3 bedrooms
  • sleeps 8
  • 60 nights min
  • Beach / lakeside relaxation
  • Nearest beach 24 mi
  • Swimming pool

Price per night from

$89

Responds fast!
avg. 1 hour 58 minutes

Price per night from

$89

Distance approx 5.39 km from Little Gasparilla Island

(34) Excellent 

Certificate of Excellence

28

Villa Zelia

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Perfect holiday” Such a nice home. Very comfortable and clean. Super pool and lounging area from sun up to sun down. We have stayed in quite a few houses on Rotonda and Villa Zeila is very definitely our new favourite!
…see more

Certificate of Excellence

Price per night from

$107

Price per night from

$107

Distance approx 5.38 km from Little Gasparilla Island

(12) Excellent 

Certificate of Excellence

24

Villa Merindah

Rotonda West / Broadmoor

Rotonda West villa

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$113

Responds fast!
avg. 2 hours 24 minutes

Price per night from

$113

Distance approx 3.87 km from Little Gasparilla Island

(7) Excellent 

14

Sunny Daze. A stunning home in perfect location

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$103

Responds fast!
avg. 2 hours 46 minutes

Price per night from

$103

Distance approx 19.46 km from Little Gasparilla Island

(1) Excellent 

33

Pine Island Paradise #2

Florida / Matlacha

Matlacha house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$198

Responds fast!
avg. 3 hours 38 minutes

Price per night from

$198

Distance approx 3.64 km from Little Gasparilla Island

(12) Excellent 

22

Glorious Gulf Villa - Waterfront property on Gulf Coast - Pure Luxury!

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool

Price per night from

$134

Price per night from

$134

Distance approx 4.85 km from Little Gasparilla Island

(61) Excellent 

30

FLORIDA GULF COAST CLOSE TO BEACHES & GOLF COURSES

Southwest Gulf Coast / Rotonda West

Rotonda West villa

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$89

Price per night from

$89

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!