Holiday rentals with a pool in Gasparilla Island

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.

Gulf Front Escape + Beach Access

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

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!

Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN

Luxury beach house with pool in a charming old-FL beach town, one of FL’s best kept secrets! New kitchen, 2 covered balconies & a walled backyard oasis. Spend sunny days by turquoise waters of the Gulf & host a cookout on the covered patio & pool. Enjoy the sea breeze while sipping your favorite beverage on the covered balcony off the living area. Lounge in style in the patio or go for a swim in the 6’ deep heated pool. You're walking distance to restaurants/bars and 57 seconds to the beach!

Sunset Beach Cottage North

Spectacular panoramic views and access to what feels like your own private 7 mile sugar sand beach. 2 master BRs with balconies overlooking the beach and ocean. Elevator, hot tub, pool, kayaks, Blackstone grill, bikes, etc. Access to Palm Island is by 3 minute car ferry - which ensures a relaxing and tropical getaway. Incredible sunsets, shelling, fishing & wildlife. There is a restaurant on the island along with gift & ice cream shop. Beautiful place to relax, unwind & embrace island life.

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

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.

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

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

Family Oasis with Heated Pool and Modern Design

Step into modern comfort in this brand-new home featuring clean design, high ceilings, and an open living space that flows seamlessly to your private patio. Enjoy cooking in the sleek kitchen or unwind in the cozy lounge with a view of the heated pool. Outside, relax under the covered sitting area or take a dip surrounded by natural beauty. Perfect for families or groups seeking a peaceful and stylish retreat.