
Holiday rentals with outdoor seating in Gasparilla Island
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Top-rated rentals with outdoor seating in Gasparilla Island
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Lake Marlin Villa 2
WELCOME to this affordable, charming and unique villa, all spotless and immaculate, cleaned with passion, love and hospitality, to honor you; The GUEST of HONOR. This 2-bed, 2-bath, 2-car garage and plenty of outdoors, offers you the comfort of feeling home, yet the adventure of your getaway vacation. Overlooking the blue waters of Lake Marlin, away from traffic and noise pollution, yet close to stores, golf clubs and main roads taking you within minutes to Manasota Key and Boca Grande Beaches.

Steps to Beach Captiva Includes CLUB & Golfcart
BOOKING SUMMER 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

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.

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!

Happily Ever After
We are off the main path and it is a quiet place to reconnect with what matters. We encourage our guests to unwind on our spacious comfy screen porch with chairs, table, and a futon chair for naps. Also use our large private maze outdoor shower. Be prepared for loads of sun and fun. Unlike most rentals ours 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.

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!

Island Getaway•Beach House•Water View•Dock•Pets
Embark on your next adventure at this unique and serene retreat that can only be reached by boat. LGI is a barrier island off the West Coast of Florida in the Gulf of Mexico between Sarasota and Ft Myers. Arrive at the island using your private boat or by boarding the water taxi, and be at our dock in just 10 minutes. There are no cars, shops, or restaurants on the island, the 7-mile beach is private and uncrowded. You can explore LGI by renting a golf cart or by walking

Luxury Retreats at Boca Grande - Boca Bay Watch
Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

The Loft on Park Ave--Boca Grande FL
We survived the old 1-2 of Huricaines, Helene and Milton and are ready to host you! A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

Waterfront Villa Shellflower with private pool
Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.
Popular amenities for outdoor seating rentals in Gasparilla Island
House rentals with outdoor seating

Island Escape • Dock Access • Quiet Beaches

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

Last Minute-Villa Bahama Bay-kayaks, pool, view

Turtle Bay - minutes to Boca Grande!

Waterfront Oasis with Boat Lift & Hot Tub

Huge Pool, Gulf Coast Luxury, Peace & Quiet, Bikes

Waterfront 3bdr 2ba Beaches Golfing Fishing

Beachfront | Pvt Fishing Dock, Shelling, Sunrises
Apartment rentals with outdoor seating

*Recently Updated* Cozy Oasis, centrally located

Starfish 2A | On Manasota Key | Pet Friendly

Beach/Sunset Bay/Sunrise Relax/Island Living

The Oz Tree House 2.9 m beach

Lido Key FL Studio/Efficiency 5

Stylish + Modern! 2 bed 2 bath. 1 block to beach!

BeachBay SeaHouse (1519)

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach
Apartment rentals with outdoor seating

Sunset Beach

Rare walkout condo on Sanibel 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

Studio, pool, private beach, boat dock shark teeth

100+ 5 Star Reviews and Right on The Beach!
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
- House rentals Gasparilla Island
- Rentals with a patio Gasparilla Island
- Family-friendly rentals Gasparilla Island
- Rentals with pools Gasparilla Island
- Rentals with beach access Gasparilla Island
- Rentals with a washing machine and dryer 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
- Bonita National Golf & Country Club
- Heritage Bay Golf & Country Club
- Clam Pass Park
- Marie Selby Botanical Gardens
- Blind Pass Beach
- North Jetty Beach
- South Jetty Beach
- Florida Gulf Coast University
- Edison & Ford Winter Estates
- Boca Grande Pass
- Tara Golf & Country Club
- Esplanade Golf & Country Club of Naples




