Vacation rentals in Pine Island

A boat deck is presented with a shaded area featuring a built-in grill and multiple seating arrangements. Lush green grass leads from a paved pathway to the water's edge, while palm trees and tranquil waters create a serene setting.

4.99 out of 5 average rating, 130 reviews

Golf Cart, Kayaks, Pedal Boat Included •Waterfront

Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

Guest suite in Spring Hill

The bathroom features a freestanding bathtub and two elegant showerheads within a marble-tiled enclosure. Natural light enters through a round window, highlighting the floral accents on the counter. Gold fixtures add a luxurious touch to the modern design.

4.99 out of 5 average rating, 212 reviews

Relaxing private suite, Air bath tub, Safe area

Charm and comfort await you in our private Airbnb suite. This spacious suite offers a queen bed and a queen sofa bed, ideal for families or small groups. Enjoy the 55” TV or relax in the cozy reading chair. The compact kitchen is fully equipped and includes a large fridge. The immaculate bathroom features a double shower, double sink, Jacuzzi tub, and a bright window behind the tub that fills the space with warm natural light. Perfect for a peaceful, unforgettable stay. Welcome to your getaway!

A charming cottage exterior is surrounded by tropical trees and well-maintained grass. The building features a mix of blue siding and stone accents, while large windows offer natural light. A cozy patio area with lounge chairs invites relaxation.

4.93 out of 5 average rating, 240 reviews

Weeki Wachee, Florida Entire House- 2 bed 2 bath

Come and relax in our newly remodeled river front cottage. This spacious two bedroom two full bath home sits nestled between beautiful tropical trees on the crystal clear river that leads out to the gulf of mexico. The 20 x 20 master suite consist of a king bed, custom two person rain shower and walk out private balcony. First level has an open floor plan with a fully stocked kitchen ready to entertain family and friends. The garage has 6 kayaks, life jackets, fishing gear, washer and dryer.

4.98 out of 5 average rating, 122 reviews

The house stands elevated on stilts, featuring a wrap-around balcony with white railings. The exterior is a soft yellow, complemented by green foliage. A set of stairs leads to the entrance, while a spacious parking area is visible beneath the structure.

Home in Crystal River

Undebatable

This one bedroom house offers one queen bed and a pull-out sofa to sleep a total of 4 people. The house offers a private boat ramp, docks, and quick access to the gulf. Includes Wifi, 2TVs, washer/drier, fire pit, grill, coffee maker. Enjoy sunsets, nature walks, and fishing from the docks. Clean, Clean, Clean! EVERYTHING is washed after each guest including sheets, towels, All blankets, bed comforters, and even decorative pillow cases. All handles, knobs, remotes and shower are sanitized.

A screened-in outdoor space features a large patio area with several lounge chairs and a dining table, all overlooking the river. A kayak is stored nearby, and a built-in ladder leads down to the water for convenient access.

4.98 out of 5 average rating, 165 reviews

Wasted Time on the Weeki Wachee - Kayak & Manatees

Manatees, fishing, kayaks, crystal clear water and the best location await you at "Wasted Time," our waterfront retreat on the beautiful Weeki Wachee river, minutes from Rogers Park. This 2/2 stilt home is comfortably furnished, sleeps 6 and comes complete with all the essentials and toys you could imagine, including boat dock. It features a large, screened in balcony patio overlooking the river, and an entire screened in entertaining space underneath the home. Direct access to the Gulf!

An aerial view showcases the property with a spacious pool integrated into the backyard. A well-maintained dock extends into the water, illuminated by a green light, accompanied by colorful kayaks. Nearby, palm trees add greenery to the inviting outdoor space.

4.91 out of 5 average rating, 107 reviews

Waterfront home heated pool+jacuzzi+game room+golf

Bring your boat or rent nearby! Minutes to prime SCALLOPING waters. Enjoy a HEATED pool, jacuzzi, putting green, ping pong table, massage chair, arcade basketball, paddle boards, kayaks, bicycles, four jetski docks & boat dock. FISH CLEANING STATION ON DOCK. Open floor plan with 3 BR, 3 BA and comfortably sleeps 16. Near boat ramp w/ access to Weeki Wachee springs. Great home for sunset cruises, scallops, dolphin &manatee watching, minutes to bike and hiking trails! Pet friendly!

4.96 out of 5 average rating, 292 reviews

A cozy living area features a turquoise and white beach-themed couch, complemented by a neutral armchair. A coffee table sits in front of a flat-screen TV on a white mantel. Soft lighting is provided by lamps near the windows, which are adorned with sheer curtains.

Cottage in Weeki Wachee

The Hideaway - Quaint and Peaceful Cottage

1.5 miles from Weeki Wachee State Park. Charming, quiet, quaint cottage, beach theme, quiet neighborhood. 2 bedrooms, 1 bathroom. Utilities, flat screen TV, cable, Netflix, wireless internet, DVD player, DVDs, towels and linens. Fully equipped kitchen with pots, pans, utensils, plates, glasses, coffee cups, wine glasses, coffee maker, air fryer, toaster and blender. Outdoor sitting area with a charcoal grill and a fire pit. Bring boat or kayaks. Park your boat on the property.

4.97 out of 5 average rating, 123 reviews

The stilt home features a spacious outdoor area with white Adirondack chairs arranged on a wooden deck. Sturdy stairs lead to the entrance, surrounded by palm trees. A clear blue sky and soft clouds provide a serene backdrop, highlighting the inviting nature of this unique property.

Home in Crystal River

Stilted 2BR canal home, full kitchen, yard, pets!

This unique place has a style all its own. Nestled upon an actual island within the Ozello Keys, Crystal River! Backwater canals to the Gulf of Mexico is the view from this loft style, stilt home. Recently renovated with all the conveniences guests love into the overall design. The property offers plenty of parking for all your toys (RV's require prior Host approval). Easily fits up to 8 vehicles. Dog friendly! FOUR Kayaks/Paddles included with your stay! Fully equipped home!

5 out of 5 average rating, 120 reviews

The kitchen features light turquoise walls and dark wood cabinetry. Open shelving displays dishware and decorative items. A stainless steel stove and microwave are installed, with a large sink beneath a window. Counter space is available for meal preparation and dining.

Home in Sea Pines

Rachel's Place

Hudson is the best kept secret in Florida. This 2/2 is located just 200 yards from the Gulf of Mexico in the beautiful Sea Pines development. This home is nestled next to thousands of acres of wildlife bird sanctuary. There are kayak trails to follow for hours. Redfish, Sea trout and Mangrove snapper are abundant. This beautifully decorated home is well stocked with anything you may need. There are 2 Kayaks, one two person and one single, 2 adult bikes, and fishing equipment.

A river house is depicted, featuring a wide deck with yellow railings. Below, a sandy area is surrounded by stones, with two blue lounge chairs and a sliding board leading into the water. Kayaks and a boat are visible nearby, along with greenery and a clear blue sky.

4.98 out of 5 average rating, 198 reviews

Riverfront Escape on the Weeki Wachee with Kayaks

Relax and enjoy the peaceful beauty of the Weeki Wachee River in this riverfront retreat with kayaks included and boat rentals available. Our 2BR/2BA home sleeps 8 with two queen beds and two futons, perfect for families and friends. Lounge on the deck, sip drinks in the lanai, or launch into crystal-clear springs for kayaking and wildlife watching. Minutes from Weeki Wachee Springs State Park, beaches, dining, and shopping — the ideal mix of adventure and relaxation.

A serene outdoor patio area features blue Adirondack chairs arranged around a central fire pit, with a backdrop of lush greenery and clear waters of the Weeki Wachee River. The setting promotes a peaceful connection to nature, inviting relaxation and enjoyment of the surroundings.

4.99 out of 5 average rating, 353 reviews

Sasquatch Hideaway: Enjoy Clear Main River Waters

Trust me, you want to be on the main river with direct access to the clear waters of the Weeki Wachee. There's a preserve across the river providing added privacy, and just around the corner from Hospital Hole where manatees love to congregate. Our home has been COMPLETELY updated and can accommodate your large group with four large bedrooms! Bring your boat to tie up or use the six single kayaks and a three person canoe provided.

4.98 out of 5 average rating, 168 reviews

An outdoor porch features a two-person Jacuzzi, inviting relaxation while overlooking a lake. Warm lighting is provided by lanterns, creating an ambient atmosphere against the backdrop of a colorful sunset and silhouettes of trees.

Tiny home in Dade City

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, delight in the opportunity to interact with our friendly farm animals, adding a touch of rural charm to your agritourism escape.

Popular amenities for Pine Island vacation rentals

Free parking on premises

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Pine Island house rentals

4.92 out of 5 average rating, 113 reviews

A waterfront home is nestled among lush trees, reflecting beautifully on the calm canal waters. A large outdoor patio with shaded seating and a relaxing area is visible. Kayaks are stored nearby, enhancing the outdoor recreational appeal of the property.

Home in Homosassa

Private waterfront house with large outdoor bar

A modern kitchen features blue cabinets and stainless steel appliances. Natural light fills the space, highlighting the countertop's clean design. The open layout connects seamlessly to a living area, which includes light-colored furnishings and decorative rugs, creating a welcoming environment.

4.96 out of 5 average rating, 112 reviews

Weeki Wachee River Escape Waterfront Home w/Kayaks

4.95 out of 5 average rating, 114 reviews

A wooden dock extends over calm waters, framed by lush greenery and tall trees. Kayaks are secured at the edge, ready for use. The tranquil scene reflects clear blue skies and invites relaxation in a natural setting.

Home in Homosassa

The Banyon House 2br 2Ba on Canal + Kayaks

4.98 out of 5 average rating, 50 reviews

HoLiD@Y Re@dY-Fla RiverVibe-Early/Late Ck-in & out

A charming pirate-themed home on stilts sits surrounded by lush greenery. The elevated structure features a porch with seating, providing a view of the tranquil river below, where kayaks can be seen ready for use. The inviting space offers a comfortable atmosphere for relaxation.

4.91 out of 5 average rating, 182 reviews

Weeki Wachee Pirate House-6703 W. Richard Dr.

The modern kitchen features warm wooden cabinets and a spacious layout. Stainless steel appliances are complemented by a large granite countertop. A double sink and ample storage are present, with natural light illuminating the area from nearby windows.

4.92 out of 5 average rating, 104 reviews

Waterfront home, boat rental 80 cheapest around!

A heated pool is framed by a spacious deck, offering access via a sturdy ladder. Colorful loungers line the pool area, alongside a picnic table under a shaded umbrella. Lush green grass and water views enhance the outdoor setting, inviting relaxation.

5 out of 5 average rating, 95 reviews

Waterfront | Dock | Heated Pool | Kayaks | Beach

A spacious pergola provides shaded seating on a paved patio, surrounded by lush green grass. Underneath, comfortable furniture encircles a central fire pit. A serene sunset casts vibrant colors on the sky, creating a tranquil ambiance perfect for relaxation.

4.98 out of 5 average rating, 59 reviews

Sunshine Escape Hernando Beach Direct Gulf Access

Other great vacation rentals in Pine Island

4.98 out of 5 average rating, 57 reviews

A charming red house with a wooden staircase leading to the entrance. Surrounded by lush greenery, the property is set within a gravel area, with mature trees providing shade and a sense of tranquility.

Home in Homosassa

Mason Creek River House

A spacious outdoor area features a hot tub with bubbling water, surrounded by a screened patio. A swimming pool gleams in the sunlight, while a vibrant tree house play area with a slide and swing set adds a colorful touch to the yard.

4.99 out of 5 average rating, 83 reviews

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring

4.95 out of 5 average rating, 55 reviews

A donkey with large ears and a gentle expression stands close to a fence. Green grass and trees create a tranquil rural background, while a pig can be seen in the distance, adding to the farm-like atmosphere.

Tiny home in Dade City

Dade City Farm Stay

5 out of 5 average rating, 98 reviews

A covered outdoor seating area features four dark blue Adirondack chairs arranged around a small fire pit. Wooden decking provides a warm contrast underfoot, while lush greenery lines the waterway in the background, enhancing the serene riverside setting.

Cabin in Spring Hill

A Frame Stream Dream Cedar Cabin on Weeki Wachee

5 out of 5 average rating, 27 reviews

A charming exterior showcases a single-story cabin with a covered porch, framed by lush greenery. The porch features comfortable seating arrangements and potted plants. Wood paneling enhances the rustic appeal, while a welcoming entrance is visible to the left.

Cottage in Spring Hill

Breezy Botanical Bungalow

4.99 out of 5 average rating, 140 reviews

The image features a silver Airstream trailer positioned under a covered wooden structure. A fire pit sits in the foreground, surrounded by a circular metal grate. Rustic wooden benches are placed nearby, and a log rests on the sandy ground, creating a cozy outdoor gathering space.

Camper/RV in Spring Hill

Weeki Waterfront Airstream Glamping Experience

A screened-in pool area features a refreshing blue pool surrounded by lounging chairs. A cozy seating arrangement is positioned nearby, complemented by vibrant cushions. Sunlight filters through the mesh ceiling, highlighting the smooth patio surface and the surrounding lush greenery.

4.96 out of 5 average rating, 27 reviews

Misol Oasis Home!