Beach house vacation rentals in Pine Island

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Top-rated beach house rentals in Pine Island

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Guest favorite

An outdoor backyard area features a hot tub surrounded by palm trees and ambient lighting. Several Adirondack chairs are arranged around a small table on a gravel surface. Stairs lead to an upper level, creating a layered outdoor space for relaxation.

Home in Indian Rocks Beach

4.97 out of 5 average rating, 190 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

Top guest favorite

Home in Clermont

5 out of 5 average rating, 37 reviews

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.

Guest favorite

Two individuals enjoy a calm river setting, one on a kayak and the other on a stand-up paddleboard. Lush green trees line the clear water, with sunlight filtering through the leaves, enhancing the tranquil outdoor experience.

Home in Spring Hill

4.89 out of 5 average rating, 56 reviews

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

Guest favorite

A sandy outdoor area is presented, featuring a thatched-roof tiki hut and several white Adirondack chairs arranged in front. Tropical plants and palm trees add natural elements to the landscape, with a clear view of the beach visible in the background under a bright blue sky.

Home in Indian Rocks Beach

5 out of 5 average rating, 9 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.

Guest favorite

Home in Weeki Wachee

4.96 out of 5 average rating, 25 reviews

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.

Guest favorite

A rectangular saltwater pool is highlighted within a screened enclosure, offering clear views of the blue sky above. Lounge chairs are positioned around the pool, alongside a spa with a stone surround. Lush greenery is visible in the background, contributing to a serene outdoor setting.

Home in Crystal Beach

4.98 out of 5 average rating, 53 reviews

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.

Superhost

A spacious living area is highlighted by large arched windows, allowing ample natural light. A coffee table with a wood finish is centrally placed on a patterned rug. Two comfortable sofas are adorned with decorative pillows, and a dining area is visible in the background.

Home in Indian Rocks Beach

4.88 out of 5 average rating, 148 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!

Guest favorite

Home in Oldsmar

4.94 out of 5 average rating, 64 reviews

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.

Top guest favorite

A beach deck is shown with turquoise lounge chairs and an umbrella, overlooking the sandy shore and the ocean. The setting sun casts warm light across the water, enhancing the atmosphere. Steps lead from the deck to the beach, creating easy access.

Home in Indian Rocks Beach

4.92 out of 5 average rating, 131 reviews

High end Beach heaven: 3 private decks, Sleeps 10!

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

Guest favorite

An inviting inground pool is surrounded by a spacious patio area, featuring sun loungers and a shaded outdoor bar. The water's surface reflects the clear blue sky, while a serene water view is visible beyond the pool, creating a relaxing atmosphere.

Home in Hernando Beach

4.87 out of 5 average rating, 15 reviews

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.

Guest favorite

An outdoor dining area features a wooden table set with two glasses and a blue bottle. A vibrant sunset paints the sky in hues of orange, pink, and purple, reflecting off the calm water and surrounding vegetation.

Home in Spring Hill

4.96 out of 5 average rating, 51 reviews

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.

Guest favorite

The image features a serene waterfront setting with three kayakers paddling on calm waters, surrounded by lush greenery. A wooden dock extends into the canal, providing access to the water. Several kayaks are neatly arranged on the shore, indicating available water activities.

Home in Spring Hill

4.94 out of 5 average rating, 52 reviews

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 Kayaksand a paddleboard are included. Ideally located close the river, yet without the crowds of kayakers. Old Florida tranquil charm offered here.