Beach house holiday rentals in Pine Island

4.97 out of 5 average rating, 32 reviews

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.

4.97 out of 5 average rating, 185 reviews

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 Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three 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 Beach House is in a quite neighborhood and walking distance from restaurants,bars and stores. BTR#209

Superhost

Home in Spring Hill

4.78 out of 5 average rating, 68 reviews

MainRiver-LG yard, 10Kayak, firepit,2 full kitchen

Escape to our updated main riverfront home on the pristine Weeki Wachee River. Offering 10 kayaks! Sleeps up to 14 guests with 2 FULL KITCHENS, modern amenities & spacious home. Enjoy outdoor living with a fire pit, gazebo, outdoor TV's, an outdoor shower, & a patio with ceiling fans overlooking the river. Conveniently; located upriver from Hospital Hole, Rogers Park, & the Upper Deck. Bring or Rent a boat dock behind our house ($60.- motorized vessel Fee). If it has a motor, you pay the fee.

5 out of 5 average rating, 5 reviews

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.

4.96 out of 5 average rating, 23 reviews

Home in Weeki Wachee

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.

4.88 out of 5 average rating, 145 reviews

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!

4.93 out of 5 average rating, 59 reviews

Home in Oldsmar

Amazing Private Beach Home

5⭐⭐⭐⭐⭐ Service & Accommodations Welcome to our stunning waterfront retreat with a million-dollar view! Nestled in a peaceful cul-de-sac on Oldsmar's picturesque Waterfront Shore Boulevard, this elevated home offers a truly extraordinary experience. Boasting a half-acre of land, this unique property commands panoramic vistas of the glistening Tampa Bay waters. Prepare to be captivated by the 165 feet of private water frontage, setting the stage for an unforgettable stay.

5 out of 5 average rating, 8 reviews

𖤓Beach Getaway: Pool & Steps to the Shore𖤓

NEW TO AIRBNB! Experience beach town family-fun at its finest! This stylish 4-bed, 2-bath home just blocks from the beach offers a private pool and a game room. Relax in the spacious living room, cook up a storm in the fully equipped kitchen, and unwind in the quaint beach town of Indian Rocks Beach. Take a dip in the pool, challenge friends to a game of cards, or simply soak up the sun on the beach. Don't miss out on this opportunity to create lifelong memories! BTR #2378

4.91 out of 5 average rating, 126 reviews

Ground Level Beach heaven + 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

4.99 out of 5 average rating, 105 reviews

Home in Madeira Beach

Beautiful New Home with Ocean View, Steps to Beach

Luxurious 3BR/3BA fully furnished new home that sleeps 11. Enjoy the gorgeous ocean views with two large balconies, perfectly located across the street from the beach, Caddy's restaurant and walking distance to several diverse options, and a 15-min walk to John's Pass (jet skis, fishing, restaurants, and more!) Amenities: - Smart TVs in all rooms - Fully equipped Kitchen - Gas grill - Beach accessories - Board Games - Family friendly

4.86 out of 5 average rating, 14 reviews

Home in Hernando Beach

Paradise Point

Relax with the whole family at this peaceful home. Beautiful sunsets and water views. Enclosed patio, inground pool, outdoor bar with bathroom, laundry room, private boat dock. Boat rentals available @ Hernando Beach Motel. 5 minutes from Weeki Wachee preserves that include bike, walking trails, bird watching, and lakes. Close to Walmart, restaurants, bars with music. 1 hr to Tampa, 2 hrs to Disney Pine Island Beach 3 miles away.