Holiday houses in Gasparilla

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Top-rated holiday rentals in Gasparilla

Guests agree: these stays are highly rated for location, cleanliness and more.

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The beach house stands prominently against a vibrant sunset sky, showcasing its welcoming façade. A sandy path leads through lush landscaping, guiding the eye toward the tranquil waters in the background. The scene radiates an inviting coastal charm, melding structure and nature.
Home in Placida
4.93 out of 5 average rating, 43 reviews

#1 House in #1 Location on LGI

🔝6 REASONS WHY CocoHut is the #1 HOUSE in the #1 LOCATION on 🏝️: 1. PANORAMIC VIEWS 🪟Floor-to-ceiling windows across the entire beachfront 2. SCREENED-IN LANAI 🌅Enjoy being outside more -especially for sunset dining 3. 🛏️ 3 MASTERS with MODERN, LUXURIOUS, EN-SUITES: 2 kings, 1 queen + 4th bedroom 4. 🤫 UNSURPASSED PRIVACY, QUIET & SECLUSION 🚫No overlooking neighbors thanks to 2 adjoining vacant lots 5. 😍 PURE BEACH VIEW 🛖Not spoilt by houses in the water 6. WIDEST SECTION OF SAND BEACH

Top Guest favourite
A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.
Home in Captiva
4.96 out of 5 average rating, 49 reviews

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

Top Guest favourite
A bright, airy living area features large windows showcasing panoramic Gulf views. A spacious seating arrangement is positioned around a central coffee table, inviting relaxation. The coastal-inspired decor complements the natural light that floods the space, enhancing the serene atmosphere of the beachfront retreat.
Home in Captiva
5 out of 5 average rating, 17 reviews

Beachfront Oasis w/ Golf Cart and Paddle Boards!

💰No nickel & diming : AirBnb & cleaning fees included! 🤝 local concierge support for a stress-free stay! 🏖️ Beachfront paradise, bordered by untouched nature on both sides— serene, and truly private 🚲 2 bikes + 🛶 2 paddleboards included for island adventures on land and sea 🛺 Golf cart provided for carefree island cruising 🛏️ Oversized primary suite: king bed, lounge areas, desk & full ensuite bath 🏡 Detached casita with private king suite—ideal for guests, couples, or quiet retreats!

Top Guest favourite
Home in Cape Coral
5 out of 5 average rating, 13 reviews

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Top Guest favourite
Cottage in Placida
4.99 out of 5 average rating, 72 reviews

Island Getaway•Beach House•Dock•Pet Friendly

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off Florida’s West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

Guest favourite
The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.
Home in Placida
4.89 out of 5 average rating, 27 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

Welcome to the most secluded spot on Little Gasparilla Island! Our Beach Cottage property is on the beach with all-natural surroundings: a state park, a mangrove lagoon, and the Gulf of Mexico. It boasts front views of the water and gorgeous island sunsets year-round. You'll have boat space on our private dock and amenities including kayaks, paddle boards, an outdoor bayside dining area, coffee bar with complimentary coffee, private grilling area, fire pit, and much more!

Top Guest favourite
An expansive open kitchen and dining area showcases sleek white cabinetry and a large kitchen island. Wooden barstools provide seating at the island, while contemporary lighting fixtures hang above. Large windows enhance the airy atmosphere, revealing a modern living space in the background.
Home in Fort Myers
4.99 out of 5 average rating, 98 reviews

Modern City Loft in Downtown River District

Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.

Top Guest favourite
Cottage in Little Gasparilla Island
4.99 out of 5 average rating, 70 reviews

Happily Ever After

Welcome to our treehouse!! Surrounding our home are wonderful sea grapes and palms. If you like privacy look no further. We are off the main path. We encourage our guests to unwind on our spacious screen porch with chairs, and tables. Be prepared for loads of sun and fun. Our rental includes all paper products, spices, plastic ware, toiletries, coffee, tea, all linens, beach chairs, noodle, sun screen, bug spray and GOLF CART available for RENT during your stay.

Guest favourite
An aerial view captures the beachfront location of the property, showing lush greenery surrounding the home with the Gulf of Mexico in the background. The sandy beach stretches along the coastline, and a clear blue sky adds to the serene coastal environment.
Home in Englewood
5 out of 5 average rating, 14 reviews

Luxury Beachfront Property

RARE BEACHFRONT PROPERTY: This is private island living at its finest. This house boasts a beautiful open floor plan with each room having a view of the beach and Gulf of Mexico. The property is gated and has a secure backyard. Walk just steps onto the powdered beach sand and Gulf of Mexico. Property is a 30-day minimum. Minimum night rent is 7 nights. If rented for less than 30 days, we will block off the rest of the calendar days in that 30-day period.

Guest favourite
A sandy area is seen leading to calm turquoise waters, with a few palm trees standing nearby. The sky is clear and blue, complementing the tranquil beach setting. Steps can be seen leading down towards the water's edge.
Home in Englewood
4.96 out of 5 average rating, 28 reviews

Luxury Beach/Gulf Front 1 BR, hot tub & deck

Welcome to Paradise Palms. This 2nd level 1 BR is totally renovated with all new furniture, large private deck & hot tub, bedroom with king, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, plenty of closets, smart TV's, & music wing. Walk out your door to a semi private beach, and a quite, neighborhood of single family homes. There is Bay access too, Kayaks available for rent. his is a 2nd story unit with another unit below.

Top Guest favourite
An aerial view captures the Tropical Island Getaway, showcasing structures with teal roofs nestled among lush greenery. A pool is visible on the left, while the coastline stretches in the background, revealing sandy shores and the serene blue Gulf waters.
Condo in Placida
4.97 out of 5 average rating, 62 reviews

Island Getaway Pool-Ferry-Grocery Delivery Incl.

*FREE Island Grocery delivery/staging Enjoy our Locally Owned and Operated, Newly Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Gated Mainland Parking & Ferry to the Island incl. Walk the Uncrowded shelled beach with Birds, Dolphin and Manatee or Venture out for Prime Fishing & Kayaking SWFlorida has to Offer

Top Guest favourite
An open-concept living area is showcased, featuring a modern sectional sofa and a sleek coffee table. Large glass doors lead to the outdoor space, allowing natural light to fill the room. A contemporary dining area with stylish fixtures is visible in the background.
Villa in Cape Coral
5 out of 5 average rating, 66 reviews

BRAND NEW Luxury Villa w/Heated and Chilled Pool

Brand new high-end 3 bedroom 3 bath designer home, elegantly decorated with incredible views and direct no-bridge Gulf access. Come and make your lifetime memories in this elegantly appointed executive villa. Located near Matlacha, Sanibel, Fort Myers, and Naples. Extra wide canal with only trees opposite, a salt water lagoon, and just off the spreader canal means incredible solitude and privacy in your elegant oasis retreat.

Popular amenities for Gasparilla holiday rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Charlotte County
  5. Gasparilla