Gasparilla Island Holiday Houses

Gasparilla Island Holiday Homes
Florida
United States of America
Holiday Homes
Expedia.co.nz

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A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

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Our top choices for Gasparilla Island holiday homes

A spacious living room with a fireplace, two ceiling fans, a television, and a view of the outdoors.

A sunlit room with wicker furniture, a bicycle, and a ceiling fan.

A two-story building with a white exterior, a covered porch, and a staircase leading to the entrance.

A modern kitchen with white cabinets, a marble countertop, and a large refrigerator with a map.

1. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp

Bokeelia

9.4 out of 10, Exceptional, (11 reviews)

9.4/10

Exceptional

(11 reviews)

"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "

Morgan P.

The price is NZ$721

NZ$721

includes taxes & fees

13 Oct - 14 Oct

Casa Florida 🌴 waterfront home with boat ramp

A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a view of a pool through a glass door.

A single-story residential house with a garage, a small front yard, and a clear blue sky.

A modern living room with two sofas, a coffee table, and a TV displaying an advertisement.

An aerial view of a building with a flat roof, a swimming pool, and surrounding greenery.

2. Dreams Away - Sleeps 10 Pool Golf Fun

Dreams Away - Sleeps 10 Pool Golf Fun

2.0 star property

Oakland Hills

The price is NZ$773

NZ$773

includes taxes & fees

12 Oct - 13 Oct

Dreams Away - Sleeps 10 Pool Golf Fun

A modern kitchen with a central island, white cabinetry, and pendant lighting.

A modern kitchen with white cabinets, a marble island, stainless steel appliances, and pendant lighting.

A lakeside property with a dock, chairs, and a boat.

A beach at sunset with waves approaching the shore.

3. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Oakland Hills

10.0 out of 10, Exceptional, (36 reviews)

10/10

Exceptional

(36 reviews)

"Everything we needed after a long day of fishing"

WARREN R.

The price is NZ$578

NZ$578

includes taxes & fees

7 Oct - 8 Oct

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink.

A living room with a sofa, a coffee table, a TV, and a ceiling fan.

A hallway with white doors, marble flooring, and a ceiling fan.

A bathroom with a white marble floor, a large mirror, and a white vanity with drawers.

4. 2/2 Duplex on CANAL all updated; new furniture,

2/2 Duplex on CANAL all updated; new furniture,

Oakland Hills

9.6 out of 10, Exceptional, (10 reviews)

9.6/10

Exceptional

(10 reviews)

"awesome place"

Brooke P.

The price is NZ$574

NZ$574

includes taxes & fees

16 Oct - 17 Oct

2/2 Duplex on CANAL all updated; new furniture,

A multi-level house with a white exterior, a staircase, and a deck area.

A wooden deck with outdoor furniture, including a table and chairs, and a hammock.

A neatly arranged bedroom with a four-poster bed, a ceiling fan, and a television on a side table.

A beach with waves gently lapping onto the shore.

5. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

North Captiva

10.0 out of 10, Exceptional, (36 reviews)

10/10

Exceptional

(36 reviews)

"Amazing stay!Beds were comfortable, kitchen was well stocked. We would stay here again and again. "

Tanya J.

The price is NZ$2,250

NZ$2,250

includes taxes & fees

1 Nov - 2 Nov

North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

A modern kitchen with white cabinets, stainless steel appliances, and a marble floor.

A covered patio with a view of a grassy field and trees.

A bedroom with a bed, a nightstand, a ceiling fan, a window with blinds, and a door.

A hallway with white walls and a tiled floor featuring a marble pattern.

6. Canal front new everything near Boca Grande Beach

Canal front new everything near Boca Grande Beach

Oakland Hills

8.4 out of 10, Very good, (6 reviews)

8.4/10

Very good

(6 reviews)

"We stayed for one month. Property was very clean, outside finishing up on storm repairs and completed couple days after we arrived. Safe area away from noise, but close drive to beaches and restaurants."

Kristine G.

The price is NZ$552

NZ$552

includes taxes & fees

16 Oct - 17 Oct

Canal front new everything near Boca Grande Beach

An aerial view of a coastal area with several small islands connected by bridges.

A modern kitchen with a central island, wooden cabinets, and a built-in oven.

A nighttime view of a paved pathway flanked by palm trees and a building with illuminated windows.

A modern living room with a beige sectional sofa, a round armchair, a glass coffee table, and a striped rug.

7. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage

Bokeelia

10.0 out of 10, Exceptional, (51 reviews)

10/10

Exceptional

(51 reviews)

"We had a great stay, was exactly as described. The host had great communication and gave great advice for the property and surrounding area."

Jennifer D.

The price is NZ$832

NZ$832

includes taxes & fees

7 Oct - 8 Oct

NEW!! The “WATERSIDE” COTTAGE~With dockage

A beach with a clear sky, calm sea, and footprints on the sand.

A modern living room with a wooden panel wall, a flat-screen TV, a dining table with bar stools, and a sofa.

A neatly made bed with white linens, two bedside tables with lamps, and a window with curtains.

A modern living room with a sofa, a TV mounted on a wooden panel, and a kitchen area with a refrigerator, sink, and countertop.

8. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC

Englewood South

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Cute, clean, comfortable beds. Perfect for our needs."

Sharon K.

The price is NZ$416

NZ$416

includes taxes & fees

13 Oct - 14 Oct

Charming 2-bedroom house in Englewood with WiFi and AC

A modern kitchen with white cabinetry, stainless steel appliances, a granite countertop, and pendant lighting.

A serene lakeside setting with a dock, lounge chairs, and a boat.

A residential area with a large house, a grassy lawn, and a small dock with chairs.

9. WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

Oakland Hills

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"Beautiful stay!"

Terrica R.

The price is NZ$577

NZ$577

includes taxes & fees

8 Oct - 9 Oct

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

A modern kitchen with white cabinets, a marble island, pendant lighting, and a dining area with a sofa and table.

A patio with a wicker bench and a view of a golf course.

A swimming pool with lanes, a lifeguard chair, and a fenced area.

10. WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

Oakland Hills

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Beautiful stay!"

Terrica R.

The price is NZ$580

NZ$580

includes taxes & fees

7 Oct - 8 Oct

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

A spacious patio with a dining table and chairs, a sofa, and a ceiling fan.

A modern interior with a wooden console table, a mirror, and a console lamp.

A two-story house with a covered driveway, palm trees, and a pond in the background.

A swimming pool with a black metal fence, a brick deck, and a view of a lake with palm trees and houses in the background.

11. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

Bokeelia

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."

Erik B.

The price is NZ$762

NZ$762

includes taxes & fees

7 Oct - 8 Oct

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

An outdoor patio with a table and chairs, a large umbrella, and a view of a lake and greenery.

A kitchen with a central island, a dining table with chairs, a ceiling fan, and a refrigerator.

A kitchen with green cabinets, a tiled floor, and a dining area with chairs and a table.

A spacious living room with a light blue sofa, a wooden coffee table, and a dining area with a striped sofa.

12. Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.

Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.

Grove City

The price is NZ$766

NZ$766

includes taxes & fees

5 Nov - 6 Nov

Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.

A beach with footprints in the sand and a cloudy sky.

A patio with wicker furniture, a table, and a potted plant.

A dining area with a round wooden table, chairs, a coffee machine, a refrigerator, and a window with blinds.

A bed with a pillow that reads 'SANDY TOES SALTY KISSES,' a painting of sailboats above it, and two bedside tables with lamps and bowls.

13. Nautical Nook

Nautical Nook

Englewood

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"We loved our stay and it was perfect for our trip to explore the beaches and parks in the area. Clean spacious and had everything we needed. Very nice owners with extra touches of hospitality! Love this gem and will be back!"

Tracie

The price is NZ$460

NZ$460

includes taxes & fees

12 Oct - 13 Oct

Nautical Nook

A modern kitchen with a central island, stainless steel appliances, and three black bar stools.

A bathroom with a large mirror, two sinks, and a vanity with drawers and a shelf.

A covered patio with a sectional sofa, lounge chairs, and a coffee table.

A rectangular pool with a clear blue water surface, surrounded by a brick border and a glass enclosure.

14. Rotonda Retreat with Heated Pool, Golf, Beaches!

Rotonda Retreat with Heated Pool, Golf, Beaches!

Oakland Hills

9.0 out of 10, Wonderful, (21 reviews)

9.0/10

Wonderful

(21 reviews)

"We really enjoyed this property!! "

laura k.

The price is NZ$740

NZ$740

includes taxes & fees

12 Oct - 13 Oct

Rotonda Retreat with Heated Pool, Golf, Beaches!

A modern kitchen with white cabinets, stainless steel appliances, a large island with bar stools, and a view of a green landscape through the glass door.

A bedroom with a four-poster bed, a ceiling fan, a flat-screen TV mounted on the wall, and a sliding door closet.

A modern building with a covered porch, large windows, and outdoor planters.

15. Golf & Beach Retreat Firepit BBQ Near Boca Grande

Golf & Beach Retreat Firepit BBQ Near Boca Grande

Oakland Hills

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great house and place to stay"

Mike C.

The price is NZ$857

NZ$857

includes taxes & fees

7 Oct - 8 Oct

Golf & Beach Retreat Firepit BBQ Near Boca Grande

A spacious living room with a large sofa, a dark wooden dresser, and a television mounted on the wall.

A kitchen with a window, white cabinets, a sink, a plant, and two soap dispensers.

A room with a sliding glass door leading to an outdoor patio with a table and chairs.

A living room with a light grey armchair, a wooden bookshelf, and a framed picture on the wall.

16. Beach town modern cottage 3Bed/2Bath house

Beach town modern cottage 3Bed/2Bath house

Englewood East

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Host was responsive . This home was very comfortable, really liked the layout . It was light and airy. A bonus was their chairs Great location to Englewood Beach and several other beaches "

Sandi T.

The price is NZ$513

NZ$513

includes taxes & fees

7 Oct - 8 Oct

Beach town modern cottage 3Bed/2Bath house

A modern kitchen with white cabinets, a central island, pendant lighting, and a dining area with chairs and a table.

A bedroom with a bed, ceiling fan, two bedside lamps, a window with curtains, and a painting on the wall.

A modern kitchen with white cabinetry, stainless steel appliances, and pendant lighting.

A room with a glass door leading to an outdoor patio area.

17. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Oakland Hills

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Very nice stay at a beautiful new home!!"

Nancy H.

The price is NZ$697

NZ$697

includes taxes & fees

7 Oct - 8 Oct

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

A modern kitchen with stainless steel appliances, a dining area with a marble countertop, and a living room with a sofa and TV.

A sunroom with a table and chairs, large windows with blinds, and a view of the outside.

A sunroom with a table and benches, large windows with blinds, and a view of the outside.

18. 2-bedroom pool house with golf cart in Englewood, close to the beaches!

2-bedroom pool house with golf cart in Englewood, close to the beaches!

Grove City

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Great stay, great host, and a great time!"

Christopher G.

The price is NZ$539

NZ$539

includes taxes & fees

7 Oct - 8 Oct

2-bedroom pool house with golf cart in Englewood, close to the beaches!

A spacious living room with a beige sofa, a glass coffee table, and a ceiling fan.

A covered patio area with a dining table and chairs, large windows, and a ceiling fan.

A modern kitchen with white cabinets, a wooden countertop, and a stainless steel sink.

A bedroom with a bed, a ceiling fan, and a window with blinds.

19. Completely remodeled beautiful waterfront property on canal with dock

Completely remodeled beautiful waterfront property on canal with dock

Port Charlotte

9.6 out of 10, Exceptional, (74 reviews)

9.6/10

Exceptional

(74 reviews)

"The house was very clean and perfect for our stay. The canal where we could keep the boat in the water was great, close to boat ramps too. There are things there you may would forget to bring, it was cool, well decorated and felt like a home. Jim was very responsive and helpful. 5 star all the way!We look forward to staying here again in the future."

sherron c.

The price is NZ$403

NZ$403

includes taxes & fees

30 Oct - 31 Oct

Completely remodeled beautiful waterfront property on canal with dock

A spacious living room with a flat-screen TV, a ceiling fan, and a large window offering a view of the outdoors.

A ping pong table with two paddles and two balls, set on a tiled floor.

A clear blue pool with a white deck and a red and orange lounge chair.

20. HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

Rotonda Heights

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Clean, comfortable, has everything you need for a vacation"

Rick J.

The price is NZ$823

NZ$823

includes taxes & fees

7 Oct - 8 Oct

HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Gasparilla Island Hotel Reviews

Baymont by Wyndham Punta Gorda/Port Charlotte

8/10 Good

"CARING AND HELDFUL STAFF MEMBERS AND CLEAN ROOM"

MARLA June 2-night trip

Posted 3 hours ago

Baymont by Wyndham Punta Gorda/Port Charlotte

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

10/10 Excellent

"Spectacular view and pool!"

Galo 1-night trip

Posted 8 hours ago

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Wyvern Hotel, an Ascend Collection Hotel

10/10 Excellent

"Great clean room with view of the charlotte harbor. Has a nice bathroom in the rooms, very attentive staff. Rooftop bar (Perch 360) and downstairs bar 88keys were both great as well. Would stay again."

Daniel 2-night trip

Posted 8 hours ago

Wyvern Hotel, an Ascend Collection Hotel

Englewood Inn & Suites

8/10 Good

"Room was cleaned daily"

Tom 7-night trip

Posted 11 hours ago

Englewood Inn & Suites

Hampton Inn & Suites North Port

10/10 Excellent

"Great hotel. Friendly staff and very clean"

Anthony MJ 3-night trip

Posted 12 hours ago

Hampton Inn & Suites North Port

The Suites at Fishermen’s Village

10/10 Excellent

"Stay here every time I visit Florida. Highly recommend"

Dawn 6-night trip

Posted 13 hours ago

The Suites at Fishermen’s Village

Holiday Inn Express & Suites Punta Gorda by IHG

10/10 Excellent

"Room was clean, there were no cups, but that was just an oops. Breakfast was real good, lots of choices."

James 1-night trip

Posted 16 hours ago

Holiday Inn Express & Suites Punta Gorda by IHG

Manasota Key Resort

10/10 Excellent

"I was my firts time there and Loved it. Everything was perfect, clean room, all the things you need is there!"

Oriana 2-night trip

Posted 2 days ago

Manasota Key Resort

Boca Grande Hotel

10/10 Excellent

"Loved our stay!"

Ayse 2-night trip

Posted 3 days ago

Boca Grande Hotel

Find out more about Gasparilla Island

Gasparilla Island Holiday Homes information

Number of reviews	360
Accommodation	1292 Holiday Homes
Lowest Price	NZ$403
Highest Price	NZ$2,250

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Book Holiday Homes in Gasparilla Island on Expedia.com

Holiday Homes in Gasparilla Island

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gasparilla Island holiday homes

1. Casa Florida 🌴 waterfront home with boat ramp

2. Dreams Away - Sleeps 10 Pool Golf Fun

3. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

4. 2/2 Duplex on CANAL all updated; new furniture,

5. North Captiva Steps to Gulf Beaches Last Minute Offers Beach + Golf Cart + Club

6. Canal front new everything near Boca Grande Beach

7. NEW!! The “WATERSIDE” COTTAGE~With dockage

8. Charming 2-bedroom house in Englewood with WiFi and AC

9. WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

10. WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

11. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

12. Boater's Dream & Beach Haven. Direct Gulf Access! No Bridges. Englewood Getaway.

13. Nautical Nook

14. Rotonda Retreat with Heated Pool, Golf, Beaches!

15. Golf & Beach Retreat Firepit BBQ Near Boca Grande

16. Beach town modern cottage 3Bed/2Bath house

17. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

18. 2-bedroom pool house with golf cart in Englewood, close to the beaches!

19. Completely remodeled beautiful waterfront property on canal with dock

20. HEATED POOL NR.BEACH-MASS. CHAIR-BBQ-LANAI-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

Find holiday rentals that suit your style

Top Gasparilla Island Hotel Reviews

Baymont by Wyndham Punta Gorda/Port Charlotte

Find out more about Gasparilla Island

Gasparilla Island Holiday Homes information

Explore a world of travel with Expedia