Beach house holiday rentals in Pine Island

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.

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!

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

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

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.

Indian Rocks Retreat | Panoramic Ocean-View Deck

Discover your dream coastal escape at the "Somerset House," a beautifully appointed 4-bedroom, 2-bath vacation rental in Indian Rocks Beach. This tropical retreat, nestled under a canopy of swaying palm trees, offers a peaceful sanctuary for up to 8 guests. Picture yourself unwinding in a hammock on the spacious, water-facing deck as you watch the sun dip below the horizon, casting golden hues across the Gulf.

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.