Beach house holiday rentals in Pine Island

Beach access! Private Pool! Whole house 2 Kitchens

This PRIVATE oasis has beach access off the pool patio, just a 2 minute walk down the shell lined Beach Trail! Boasting full remodel in 2025 with two kitchens & PRIVATE POOL, outdoor shower & multiple patio areas! Located on the beach side of Gulf Blvd, we are a fan favorite among returning guests who enjoy many restaurants within walking distance! Four parking spaces included at no additional charge. Dock your boat just 3 blocks away at Harborside Marina! Golf cart rental also available nearby.

Lakefront home - country - check for seasonal rate

Your family will be close to everything when you stay at this centrally located home. It is close to Orlando attractions such as Disney Parks, Universal Studios, Legoland, Many places to golf, short drive to most of Florida's natural springs and only an hour and half to the west or east cost of Fl. It is a wonderful place to relax and Play in the water or fish off the dock and watch sunsets. It is a beautiful country setting and is great for just taking a walk or hiking, you can go for miles.

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home.Sand,sun and ocean breeze are waiting for you.Our modern BeachHouse is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built four story house with nice and private backyard,heated pool,hot tub and beautiful rooftop.We have everything that you need for bigger groups of families to relax on your Beach vacation.Our BeachHouse is in a quite neighborhood and walking distance from restaurants,bars and stores. BTR#2099

Hidden Jim-Clear Main River house kayak, preserve

Main River cottage Your outdoor adventures while staying directly on the Weeki Wachee Springs River. This unpretentious one-story cottage is a great place to immerse yourself in nature. Directly across the river is the Weeki Wachee Preserve. People watching is the best In Summer/Spring. Fall/Winter is peaceful. Enjoy local restaurants, vineyards, & breweries, or catch the famous Mermaid Show just 5 min away. With Tampa Airport 1/hr & Disney 1.5 hrs away, your ultimate getaway awaits. Book it

Oceanfront Boho Bungalow Breeze

Step into the soul of Indian Rocks Beach with this newly restored stone beach cottage, offering direct access to the sand that blends nostalgic charm with modern luxury. This coastal gem is one of IRB’s original stone cottages, lovingly updated while preserving its unique architectural character. Inside, you’ll find a boho-inspired interior with all the modern conveniences. Walk barefoot from your door to the shore. This is not your average rental—it’s an authentic luxurious experience.

Island/Beachfront House - Majestic Sunsets

Welcome to the stunning, newly-built (2023) Beachfront Bliss! We are directly on the beach in the most desirable west side of the island. Starting with the most spectacular panoramic views of the Gulf, you'll find yourself mesmerized by the seemingly endless water view and beautiful sunsets. See dolphins and wildlife from the covered deck. Or rest in a hammock on the sandy beach for a closer look. Feel a serene constant sea breeze and the sound of gentle waves lapping along the beach.

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Welcome to Seaside Sanctuary 🌊🌅 – Your Ultimate Waterfront Escape Nestled in charming Crystal Beach, this spacious 4-bedroom, 2.5-bath retreat perfectly blends luxury, comfort, and coastal fun. Go kayaking from your direct Intracoastal access, soak in unobstructed sunsets, relax in the hot tub, challenge friends in the game room, or grill a delicious meal on the patio 🥙. Perfect for family reunions, bestie getaways, wedding weekends—or simply because you deserve a seaside escape!

Custom Waterfront 3BR Paradise/Salt WaterPool-Spa

Welcome to your Crystal Beach paradise w/spectacular sunrises over the water from your pool deck, Gulf of Mexico sunsets from front porch. Custom open concept gourmet kitchen with island and butler pantry, spacious 3 bedrooms and 2 spa style bathrooms for you and your guests to enjoy. Step out your sliding doors to a covered Lanai with ceiling fans and sound system to your salt water pool and spa with waterfall. Hotel style lounge chairs, couches, covered dining and Weber grill awaits.

Historic Lakefront Vineyard

Welcome to our lakeside vineyard! The Osprey View is a 10 acre property just 15 minutes outside of Tampa and perfect for a relaxing getaway! Surround yourself with 6 acres of muscadine grapevines inside our 125 year old, 2600 square foot Farmhouse. The home boasts living space for up to 10 guests. The front patio will take your breath away! Imagine 3,500 square feet of covered patio space overlooking the grapevines and beautiful Lake Thonotosassa! We look forward to hosting you!

Luxury 3 Bedroom Beach Home with Game Room!

The perfect beach home DOES exist! Perfectly positioned 2 blocks away from direct beach access, kick up your feet & relax in our cozy 3 bedroom + 2.5 bathrooms with a killer garage space turned game room! While you’re not soaking up the sun on the beach, hang out downstairs and battle it out between air hockey, foosball, giant Jenga & Connect 4 and board games such as Cards Against Humanity. You'll feel right at home in our newly renovated & professionally decorated vacation home!

Vay-cay Canalside at Sunshine & Splashes Cottage

Come and enjoy Sunshine Splash Down; a large new waterfront home on Big Cypress Canal; just a short paddle down canal to the Weeki Wachee river. Manatees frequent the canal year round. The home is spacious with a 28 ft porch overlooking the water. 6 Kayaks and a paddleboard are included. Ideally located close to the river, yet without the crowds of kayakers. Old Florida tranquil charm offered here. Enjoy the river longer; great discount of 45% on monthly rentals.

High end Beach heaven: Sleeps 10, 3 private decks

Ideal for those who appreciate single-level living. 3 bedrooms & 2 baths located on the main floor, & loft-style 4th bedroom upstairs. Enjoy 3 decks!: a private beach deck just a 30-second walk away + front & upper decks offering partial ocean views perfect for morning coffee or for cocktails. The primary booking guest must be at least 27 years old, stay on-site during the reservation, and provide valid government-issued ID to host within 24 hrs of booking. Vtr -1609