Vacation rentals in Pine Island

4.99 out of 5 average rating, 136 reviews

Home in Hernando Beach

Firepit, Golf Cart, Kayaks, Pedal Boat, Fishing!

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!!

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.

4.92 out of 5 average rating, 206 reviews

Weeki Wachee Pirate House - 6703 W. Richard Dr.

Embellish in this once in a lifetime, perfect getaway on Weeki Wachee River. A local favorite! Fully furnished pirate themed, 500 sq ft home with 1 bedroom 1 bath full kitchen and sofa bed. It has everything needed to create unique memories. Swim with manatees in the crystal clear spring-fed river. Have your coffee on the porch over looking the water and your favorite drink around the fire at night. Kayaks are included. Minutes from Weeki Wachee mermaids, Pine Island Beach and Homosassa Springs.

Place to stay in Mount Dora

The exterior of the waterfront residence is illuminated with colorful string lights, creating a festive ambiance. A spacious patio area is visible, featuring a dining table and seating. Large glass windows allow for views of the living space inside, enhancing the open-air feel.

4.98 out of 5 average rating, 265 reviews

The Boat House on Lake Dora - Downtown Waterfront

WATERFRONT! The Boat House is an 800sf private residence built directly over Lake Dora offering panoramic lakefront views. Located on Mount Dora's Famous Boat House Row, right in the heart of downtown Mount Dora, where you can roll out of bed and walk a few steps to one of the quaint coffee shops. The Boat House was once a tin boat shed with floors open to the water and housed two boats. Today, you will find warm, cozy furnishings, comfortable beds, a quiet location and sunsets every evening!

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, 254 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, 144 reviews

The exterior of a converted Chinook helicopter is showcased, featuring a fenced area and a welcoming entryway. The surrounding landscape includes greenery and sky, with details of the helicopter's design visible, blending seamlessly into the natural setting.

Plane in Brooksville

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

4.98 out of 5 average rating, 168 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.97 out of 5 average rating, 135 reviews

The stilt home features a light-colored exterior with multiple windows allowing natural light. A wide staircase leads to the covered porch, surrounded by green grass and palm trees. The backdrop includes a clear blue sky, emphasizing the coastal setting.

Cottage in Crystal River

Ozello Keys Cottage on Crystal Bay

2/1 Ozello coastal cottage on stilts surrounded by nature, tranquility, and endless views of the water and estuary. Nature lovers paradise. World renowned fishing and scalloping. Regular dolphin and manatee sightings. Relax with the whole family on the large screened back porch providing gorgeous views of the Nature Coast and stunning sunrises over the salt marsh. The open floor plan opens up to a large screened porch with a dining and lounging space with private and expansive water views.

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.

4.95 out of 5 average rating, 127 reviews

Weeki Wachee River Escape Waterfront Home w/Kayaks

Stay at this Weeki Wachee River Escape! 2 BR, 2 BA, updated coastal-themed home on the river that sleeps up to 6 people with a floating dock! The main house has a large master BR with king bed, full bath, beautiful kitchen and living room with bunk beds (twin and full) The patio is screened-in and has a dining and seating area. The little house has a queen bed, full bath and washer/dryer. Relax out back by a fire pit or cookout on the grill and enjoy the 5 kayaks and paddle board!

A stone pathway leads to a small fire pit, surrounded by two brightly colored chairs. The serene waterfront scene includes a wooden dock and a canal lined with houses and greenery, reflecting a tranquil outdoor space.

4.91 out of 5 average rating, 265 reviews

"Ruf'n It" On The River w/kayaks

"Ruf'n IT" is a 2/1 Waterfront home w/ TV/WiFi just off the main river w/ 7 single kayaks and a youth paddle board. There is dock space for your boat, canoe, or kayaks w/ space to park your trailer. The living space provides 1250 squ ft w/dining area. Enjoy the peace and quiet on the screened lanai and a spiral staircase up to the loft w/TV and kid space. The master bedroom provides a king size bed while the 2nd bedroom has 2 queens and bunks. ASK ABOUT OUR JON BOAT RENTAL!

5 out of 5 average rating, 126 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.

4.99 out of 5 average rating, 176 reviews

A colorful cottage with a screened lanai rests along a serene river. Kayaks and a floating island are docked nearby, with reflections shimmering on the water. Lush greenery surrounds the property, creating a tranquil outdoor setting ideal for relaxation and recreation.

Cottage in Spring Hill

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

A screened-in pool area features a clear, inviting pool with a waterfall and soft blue water. Surrounding greenery provides privacy, while lounge chairs are positioned near the water. Sunlight filters through the mesh enclosure, creating a bright and airy atmosphere.

4.94 out of 5 average rating, 130 reviews

Spring Hill, Florida Quaint Paradise

The Retreat sleeps 4 guest comfortably. Our 2 bedroom, 2 bathroom home features a pool with a waterfall and fenced backyard. This quaint paradise will make you feel relaxed sitting by the pool enjoying a good book with a drink while you can hear the breeze going through the palms in the backyard. It’s located on a quiet street. But minutes away from different beaches, golf courses, shops and restaurants, attractions and parks.Something to do for the whole family.

Popular amenities for Pine Island vacation rentals

Self check-in

Free parking on premises

Gym

BBQ grill

Laptop-friendly workspace

Pine Island house rentals

4.89 out of 5 average rating, 150 reviews

Heated Pool Sun-Splashed 3 BR/2 BA Getaway

4.99 out of 5 average rating, 85 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

5 out of 5 average rating, 27 reviews

An aerial view of the stilt home, revealing a spacious concrete patio with colorful outdoor seating and a charcoal grill. The private dock extends into the water, ideal for boating activities. Surrounding greenery adds to the inviting ambiance of the property.

Home in Hernando Beach

Waterfront Gulf Oasis: Renovated 2BR - Deck & Dock

A serene canalside view features a calm waterway reflecting soft hues of pink and purple from the sunset. Lush greenery and palm trees line the banks, while several small boats are docked nearby, enhancing the tranquil waterfront atmosphere.

4.98 out of 5 average rating, 42 reviews

Nature Coast Retreats 3/2 Heated Pool, Gulf Access

4.9 out of 5 average rating, 97 reviews

An aerial view captures the stilted home and its private dock extending over calm waters. Lush greenery surrounds the property, showcasing the tranquil setting. The design of the home emphasizes open spaces, with ample access to the water for exploration and relaxation.

Home in Crystal River

Ozello Island Sunset House - Waterfront Beauty

The three-story home is situated along a river, featuring a spacious deck with seating and an expansive tree for shade. A concrete walkway leads to a floating dock, providing access to the water, while colorful plants and decor add vibrancy to the outdoor space.

4.96 out of 5 average rating, 48 reviews

Weeki Wachee Riverfront Home with Amazing View!

5 out of 5 average rating, 52 reviews

Butterfly "Season" is here!

A clear, calm waterway is observed, with vibrant greenery lining the banks. A red kayak is positioned in the foreground, leading toward two people on a paddleboard further down the channel, surrounded by the natural beauty of the area.

4.81 out of 5 average rating, 295 reviews

Boutique Above the River

Other great vacation rentals in Pine Island

5 out of 5 average rating, 5 reviews

Home in Weeki Wachee

Waterfront w/ Boat Ramp+Jacuzzi+Golf +Games+Kayaks

A light-filled living area features navy blue couches arranged around a uniquely designed coffee table with a vibrant, swirling blue and green surface. Decorative pillows adorn the seating, while a shelf displays nautical decor. The open layout leads to a dining area visible in the background.

4.94 out of 5 average rating, 34 reviews

Paradise on the Canal

4.93 out of 5 average rating, 57 reviews

Luxury getaway, Heated Pool, Weeki Wachee

Outdoor seating is provided on the deck, illuminated by string lights. Steps lead down to a grassy area, while the calm waters of the river reflect surrounding trees. A boat is docked in the distance, enhancing the serene atmosphere.

4.93 out of 5 average rating, 43 reviews

The Blue Heron | Riverfront Stay + Gulf Access

A serene outdoor space features four turquoise chairs arranged around a central fire pit. The area is paved with stones and overlooks a calm river, with greenery and a covered dock visible in the background.

4.91 out of 5 average rating, 90 reviews

Weeki Wachee Hospital Hole Oasis

Superhost

5 out of 5 average rating, 4 reviews

Pool + Great Location | Spring Hill

The exterior of a turquoise cottage is set among lush greenery and palm trees. A serene path leads to the front entrance, featuring steps flanked by white gravel and small shrubs. The inviting porch is adorned with white railings and symmetrical windows, enhancing the home's charm.

4.98 out of 5 average rating, 65 reviews

Charming Flip Flop Cottage - A perfect get away!!

An aerial view captures a well-maintained backyard deck, bordered by lush greenery, leading to a private dock on a tranquil freshwater canal. A cozy gazebo and kayaks are visible, enhancing the outdoor space's inviting feel for various recreational activities.