Beach house holiday rentals in Pine Island

New Pool • Oceanview • Walk to Beach • Bali Design

• 3 Bedrooms • 2 Modern Bathrooms (walk-in showers) • 2 Full Kitchens • 2 Living Areas • Private Pool • 80” Smart TV in main living room • 40” Smart TV in secondary unit • Walk to Beach, Restaurants, and Bars in 10min Experience the entire oceanview retreat — combining both units into one expansive 3-bedroom, 2-bath coastal compound. Perfect for extended families, groups, or multi-couple stays who want shared space with built-in privacy. Ocean views from every room across the entire property.

Capt Jack's w/SUP, Jacuzzi, Game Rm, kayaks, dock

Escape to our newly remodeled (2025) never been flooded upriver home in Weeki Wachee, FL, just 1 hour N of Tpa boasting professionally cleaned, comfortable accommodations. Enjoy a private Jacuzzi, an expansive game rm with a LG smart TV, 2 SUP, 5 Kayaks, 4 relaxing RiverTubes +, a giant float mat, & yoga mat on one of the best upriver canals just off the main river. The perfect retreat for those seeking relaxation & adventure in nature's paradise. Secure your date with a deposit while it lasts.

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!

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. 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. BeachHouse is in a quiet neighborhood and walking distance from restaurants, bars and stores. BTR#2099

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!

Hudson Waterfront Home "The Surf Shack"

We're not just a place to sleep at night; we're full of fun things to do! We are pool tables, foosball, board games, corn hole, and get togethers outside under the pergola. Use the dock to fish or spot wildlife or to simply relax. Our home is walking distance to Hudson Beach and Robert J. Strickland Park boat ramp! Ollie's on the Beach is 0.4 miles away and Sam's Beach Bar is 0.6 miles. We foresee lots of great sunsets in your future. Allow us to make your stay one of the best!

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.

Did Someone Say Heated Pool?

Discover coastal luxury in this completely remodeled, stylish 3-bedroom, 2-bath waterfront home perfectly situated in the heart of Hernando Beach. Gorgeous kitchen with quartz countertops, and stainless-steel appliances that flow into the spacious living and dining areas that showcase high end finishes. The split-bedroom floorplan offers privacy, with a primary suite with a beautifully updated bathroom. Enjoy the heated pool as it won't disappoint.

Gulf-Front Oasis | Stunning Sunsets +Nature Views!

Escape to Osowaw Oasis, a peaceful Gulf-front retreat on over an acre with 600' of waterfront. Enjoy breathtaking sunsets, coastal charm, and 2,000 sq ft of outdoor entertaining space. Lounge on the upstairs porch, launch kayaks, or watch for dolphins and manatees. Just 10 minutes from Weeki Wachee, this cozy, dog-friendly home is perfect for families, nature lovers, and anyone craving Old Florida charm.

Dolphins Cove | Direct Gulf Access, Tiki & Pool

Welcome to Dolphins Cove, a waterfront retreat in Hernando Beach North with direct Gulf access and deep water docking. Enjoy a heated pool and hot tub, tiki hut with smart TV, kayaks, and a fully fenced pet-friendly yard. Inside, relax in two living rooms, including a game room with sleeper sofa. Sleeps up to 9. Perfect for boating, families, and laid-back Nature Coast living.

Mobbly House

A cozy dwelling in the quaint neighborhood of Oldsmar. Golfcart town and 30 minutes from Clearwater Beach and Honeymoon Island state park. Mobbly House is across the street from Mobbly wildlife preserve nature park and beach on Old Tampa Bay with empower zip lines one mile away. Also check out our other listing, Fountain House if available.