
Holiday rentals with outdoor seating in Gasparilla Island
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Gasparilla Island
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

LG Beach Bungalow on Gulf w/Bay Access & deck too!
Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

Blue Laguna - Vacation in paradise!
This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Beach Chalet Gulf View
Experience the ultimate beach vacation in our stunning beachfront condo, located on the Gulf of Mexico. It offers breathtaking ocean views and direct access to pristine sandy beaches. The condo sleeps four and offers one bedroom with a king size bed with a private attached bathroom. It also has a queen size murphy bed and an additional full bathroom. The modern kitchen is fully equipped with all the essentials. Plus, the resort offers an onsite pool, fitness center, tennis courts & restaurant.

Steps to Beach Captiva Includes CLUB & Golfcart
HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

Unit #1 Free kayak/bikes/walk to beach/fullcottage
Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

Amazing Sunsets just 50 steps to uncrowded beach
Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!
Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $200/pet fee). Just steps from our private beach & 1 mile from bars and restaurants, with a free shuttle service to beaches, dining, & nightlife. Relax in comfort w/ soft beds, a spacious couch, and flat-screen smart TVs in every room & fast WiFi. We offer bikes and beach equipment. 1 mile from Manasota Key public beach. Book now for the ultimate island retreat!

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.

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!

Studio, pool, private beach, boat dock shark teeth
Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, full sofa bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach. Close to everything!!

Salty Mermaid onLittle Gasparilla Island/LGI
Charming beach house on Little Gasparilla Island (LGI) The Salty Mermaid offers a unique tropical paradise with 7 miles of undisturbed white sandy beaches. Embrace the old Florida Island vibe. Enchanted island steeped in pirate lore, legend has it, the spanish pirate Jose Gaspar, nicknamed Gasparilla, made this beautiful island his secret base hideaway. Local legends whisper of buried treasures hidden beneath the islands sandy shores. Come get Salty!

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
Popular amenities for Gasparilla Island outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Green Bamboo - saltwater pool, great backyard.

Island Escape • Dock Access • Quiet Beaches

Tropical Oasis, pool, golf, dog friendly

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*

Sunset Retreat - Private Pool Near Gulf Beaches

Upscale Getaway

Coastal Sunny Getaway | 6 Guests + Mineral Springs

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games
Apartment rentals with outdoor seating

Beach/Sunset Bay/Sunrise Relax/Island Living

The Oz Tree House 2.9 m beach

Lido Key FL Studio/Efficiency 5

Redfish Room in Matlacha

BeachBay SeaHouse (1519)

Private Apartment with sunny pool

Ready to Enjoy again! 2025: Everything is new!

Old Florida Charm near Beaches
Condo rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Sunset Beach

Rare walkout condo on Sanibel beach

The Honeymoon Suite on Siesta Key Beach

Beachfront fully equipped apartment

South Seas Resort Beach Villa 🌴 On The Beach !

Short walk to beach 4, King bed, Dog Friendly

On the Beach; Siesta Key SunBum Studio
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Family-friendly rentals Gasparilla Island
- Rentals with a washing machine and dryer Gasparilla Island
- House rentals Gasparilla Island
- Rentals with pools Gasparilla Island
- Rentals with a patio Gasparilla Island
- Rentals with beach access Gasparilla Island
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Siesta Beach
- Crescent Beach
- Captiva Island
- Turtle Beach
- Lido Key Beach
- Caspersen Beach
- Manasota Key Beach
- Lovers Key Beach
- Englewood Beach
- Lakewood National Golf Club
- Myakka River State Park
- Stump Pass Beach State Park
- Clam Pass Park
- Bonita National Golf & Country Club
- Marie Selby Botanical Gardens
- Heritage Bay Golf & Country Club
- Blind Pass Beach
- North Jetty Beach
- South Jetty Beach
- Edison & Ford Winter Estates
- Tara Golf & Country Club
- Esplanade Golf & Country Club of Naples
- Florida Gulf Coast University
- Boca Grande Pass




