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Vacation rentals in Pine Island

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Top-rated vacation rentals in Pine Island

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Top guest favorite
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.
Home in Spring Hill

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.

FamilyLocationQuiet

4.93 out of 5 average rating, 275 reviews
Guest favorite
A sandy area beside the canal features a wooden picnic table and several brightly colored Adirondack chairs. Kayaks are neatly arranged along the shore, while lush greenery and towering trees provide a serene backdrop overlooking the calm waters.
Home in Spring Hill

The Chubby Mermaid (Weeki Wachee)

The "Chubby Mermaid" is a brand new (2020) manatee themed 3/2 waterfront home on a pristine canal just yards away from the Weeki Wachee River. Manatees frequent the canal year round. It sits amid towering old trees, directly across the street from a nature preserve and its large 28' porch overlooks the water. Canoe and kayaks are included. Ideally located so close to the river yet without the crowds of kayakers constantly passing by, you'll enjoy the Old Florida charm and peace offered here.

FamilyLocationGetting around

4.93 out of 5 average rating, 352 reviews
Top guest favorite
Camper/RV in Spring Hill

Weeki Waterfront Airstream Glamping Experience

Nature Oasis 🤩 Glamping (Glamorous Camping) Experience in 25-foot Airstream Travel Trailer (RV) ✅ Lush forest views ✅ Tranquil waterfront location (paddle down the canal to the pristine Weeki Wachee River) ✅FREE amenities - hot tub, outdoor shower, firepit, griddle, bikes, yoga mats, kayaks, & stand-up paddle boards. SELF CARE UPGRADE is $100/person. It includes access to shared space: food forest, garden & waterfront wellness studio with experiences curated for you by your hostess.

LocationValueParks

4.99 out of 5 average rating, 177 reviews
Guest favorite
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.
Home in Hernando Beach

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/deep canal. Open floor plan with 4 BR, 3 BA and comfortably sleeps 16. Near boat ramp w/ access to Weeki Wachee springs. Great home for fishing, scallops, dolphin &manatee watching, minutes to bike and hiking trails! Pet friendly!

ValueLocationGetting around

4.91 out of 5 average rating, 139 reviews
Superhost
A spacious waterfront property is set on a canal, surrounded by greenery and palm trees. The structure features a large screened-in area, showcasing the outdoor living space and pool, while reflecting the tranquil water nearby.
Home in Spring Hill

PALM CREEK GETAWAY spring meets gulf+pool/spa

Enjoy natural spring yet only minutes kayaking to the gulf: 4BR, 3 full baths + living + dining + outdoor dining by screened & heated salt-water pool and spa ($30/nite extra) + screened patios. Get away to kayaking, scalloping, fishing, crabbing, biking, watching dolphins/manatees, fire pit, hammock in Florida sun... 5 mins drive to Weeki Wachee State Park, 7 mins drive to Pine Island, 30 mins to Homosassa, 1 hr to Tampa, 2 hrs to Disney. Close to restaurants, stores, grocery...

ValueFamilyBathroom

4.86 out of 5 average rating, 126 reviews
Superhost
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.
Home in Spring Hill

"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!

ValueFamilyWalkability

4.9 out of 5 average rating, 282 reviews
Top guest favorite
A wooden dock extends over calm waters, leading to a shaded seating area under a pergola. The two-story house features a pastel exterior and multiple outdoor spaces, surrounded by lush greenery and distant waterfront homes under a partly cloudy sky.
Home in Weeki Wachee

SEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!

The house is on the main river close to Weeki Wachee springs and has great access to the Gulf of Mexico. You can dock up to a 24' boat. It is only minutes from Pine Island Beach Park, Hernando Beach and Sun West Park. It is also about an hour and half from world renowned Clearwater beach. Get the best experience Florida can offer. You’ll love Weeki Wachee and the freshwater spring that feeds seventy two degree water year round. This house has 4 bedrooms and sleeps 10!

ValueLocationGetting around

4.99 out of 5 average rating, 188 reviews
Guest favorite
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.

FamilyLocationHospitality

4.98 out of 5 average rating, 206 reviews
Top guest favorite
The image captures the serene Weeki Wachee River, characterized by its clear waters and lush greenery lining both banks. A wooden dock with a ladder leads down to the water, while gentle ripples and blue sky complement the natural landscape.
Home in Spring Hill

Home On the River - Weeki Wachee Cabin

Escape to our peaceful Weeki Wachee River retreat, where relaxation meets adventure. Nestled on the clear part of the river, our family-friendly getaway offers everything you need for a memorable vacation. Tube down the crystal-clear waters, kayak through stunning scenery, and snorkel in the pristine river. Enjoy swimming, fishing, and wildlife sightings. Discover the perfect blend of tranquility and excitement at our Weeki Wachee River oasis.

ValueFamilyBathroom

4.98 out of 5 average rating, 105 reviews
Top guest favorite
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.
Home in Weeki Wachee

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.

LocationValueBeach

4.99 out of 5 average rating, 392 reviews
Guest favorite
Home in Weeki Wachee

Weeki Wachee Canal Home Dock AND Kayaks

Cozy Weeki Wachee canal-front home just one turn from the river! Enjoy a private dock, floating swim platform, and included kayaks & paddle board for endless fun on the water. Relax on the screened patio, gather around the fire pit, or cook out on the grill. Inside features streaming TVs, a coffee & tea station, and a separate private suite. Snowbird-friendly, pet-friendly (with approval), and ideal for family getaways.

LocationFamilyAccuracy

4.9 out of 5 average rating, 131 reviews
Top guest favorite
A wooden dock extends into a serene canal, flanked by lush palm trees and vibrant greenery. A gazebo and outdoor seating area are visible in the background, providing inviting spaces for relaxation amidst the tranquil surroundings.
Cottage in Spring Hill

PARADISE POINT on Weeki Wachee (Boat Welcome)

Find tranquility at Paradise Point, a charming, private STUDIO home so there is not a separate bedroom. Our canal feeds into the Weeki Wachee River just before Rodgers Park. Short, easy paddle, (less than a quarter mile) to the amazingly clear, turquoise rivers. Stunning views from the back porch. Don't miss breathtaking sunsets on the water and watch for manatees, dolphins, and otters. ⭐️ PLEASE NOTE: 🐾 NO pets!

FamilyValueCheckout

4.99 out of 5 average rating, 170 reviews

Popular amenities for Pine Island vacation rentals

Self check-inFree parking on premisesGymBBQ grillLaptop-friendly workspace

Pine Island house rentals

Top guest favorite
A two-story house is positioned beside a private canal, featuring large windows that invite natural light. A spacious deck with outdoor seating is visible, along with a wooden dock and a kayak moored nearby. Lush greenery and a large tree frame the scene, creating a serene atmosphere.
Home in Spring Hill

Charming River House @ Weeki Wachee!

ValueFamilyOutdoor spaces

4.97 out of 5 average rating, 126 reviews
Top guest favorite
An aerial view of a spacious three-story home is presented, bordered by lush greenery and palm trees. A private dock extends into the water, featuring seating areas for relaxation. The surrounding area is tranquil, showcasing a blend of natural and residential scenery.
Home in Spring Hill

Newly Offered-Great Location - Sleeps 12 + Kayaks

LocationValueNearby

4.98 out of 5 average rating, 115 reviews
Guest favorite
A serene canal setting is highlighted, featuring calm waters reflecting the surrounding greenery. Boating docks are visible along the banks, with multiple boats moored. Lush trees create a natural backdrop, while the peaceful atmosphere invites relaxation.
Home in Spring Hill

Flip Flop River Stop

FamilyLocationSleep quality

4.85 out of 5 average rating, 142 reviews
Top guest favorite
Home in Spring Hill

"Come Sail Away" | Gulf Waterfront Stilt House

FamilyLocationBathroom

5.0 out of 5 average rating, 21 reviews
Top guest favorite
A dining table set for six is situated on a covered deck, overlooking the Gulf waters. The sun sets in the distance, creating a gradient of colors in the sky. Palm trees frame the view, enhancing the serene atmosphere.
Home in Weeki Wachee

Island/Beachfront House - Majestic Sunsets

LocationFamilyGrill

4.98 out of 5 average rating, 43 reviews
Guest favorite
A serene waterfront view captures a vast expanse of calm water reflecting shades of blue, orange, and pink during sunset. The horizon is lined with soft clouds, enhancing the tranquil atmosphere of the beachfront. The sandy shore is visible in the foreground.
Home in Spring Hill

Pine Island Paradise in Weeki Wachee

FamilyLocationBackyard

4.87 out of 5 average rating, 95 reviews
Top guest favorite
Two teal lounge chairs are positioned on a private deck, offering a view of a calm waterway reflecting a vibrant sunset. In the background, a kayak is visible on the water, with lush greenery along the shore adding to the serene setting.
Home in Spring Hill

Pine Island Escape | Kayaks, Sand, Sunsets & Games

LocationFamilyAccuracy

5.0 out of 5 average rating, 28 reviews
Superhost
A serene view of the ocean at sunset, with vibrant hues of orange and pink reflected on the water's surface. Palm trees frame the image, while lush foliage adds to the natural setting, creating a peaceful coastal atmosphere.
Home in Weeki Wachee

Island House, Gulf Views Pine Isl., Tampa, Orlando

FamilyLocationBathroom

4.82 out of 5 average rating, 165 reviews

Other great vacation rentals in Pine Island

Top guest favorite
A large tree with branches adorned with string lights creates a warm ambiance in the outdoor area. Two wooden swings hang from the tree, surrounded by a ground covered in leaves, inviting relaxation in a serene, natural environment.
Tiny home in Spring Hill

Charm and comfy tiny house

ValueLocationBackyard

4.99 out of 5 average rating, 105 reviews
Guest favorite
A wooden bench is positioned on the water's edge, facing a calm ocean. The sunset casts a warm glow over the vast water surface, reflecting hues of orange and blue. A small boat is visible in the distance, enjoying the tranquil scene.
Cottage in Spring Hill

Gulf Sunsets! Island Life but minutes to spring!

FamilyLocationComfort

4.95 out of 5 average rating, 64 reviews
Superhost
The back deck overlooks the serene waterway, framed by a palm tree. Comfortable seating arrangements are positioned for relaxation, while large windows provide views into the home. A sunset casts warm light, creating a peaceful setting along the water's edge.
Home in Spring Hill

EPIC Weeki Wachee home - Waterfront Rogers Park

LocationValueCheck-in

4.85 out of 5 average rating, 59 reviews
Guest favorite
Home in Spring Hill

Main River: Hot Tub, Jon boat, hot tub

ValueFamilyIndoor spaces

4.8 out of 5 average rating, 51 reviews
Top guest favorite
A manatee is partially submerged in the water, surrounded by lush green vegetation. Its large body is visible among the water plants, with ripples indicating its movement. The interplay of light and shadow creates a serene atmosphere near the riverbank.
Tiny home in Spring Hill

Vintage tiny house on Weeki w/ kayaks and RV site

LocationValueCheck-in

4.93 out of 5 average rating, 80 reviews
Guest favorite
Home in Spring Hill

Waterfront at Weeki Wachee

FamilyLocationPool

5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Spring Hill

Welcome to Weeki River Escape!

FamilyLocationRiver

4.88 out of 5 average rating, 16 reviews
Top guest favorite
Home in Spring Hill

Private Garden 3 Shower, Arcade Games, Sups & Yaks

FamilyLocationNearby

4.91 out of 5 average rating, 35 reviews

All about Pine Island

Despite being the largest island off Florida’s Southwestern Gulf Coast, Pine Island has an Old Florida feel, with small villages and miles of farmland, mangroves, palm trees, and tropical fruit groves. Its secluded, small-town atmosphere is unlike the high-rise buildings and commercial businesses in the region’s more popular tourist destinations. You can spend a day or two exploring the 17-mile island’s boutiques and small waterfront restaurants, many of which feature clam and crab chowders and freshly caught seafood.

Although lacking beaches, Pine Island provides some of the best fishing in Florida. On the Matlacha Pass Bridge, which connects the island to the mainland, you’ll often see visitors reeling in redfish, snook, grouper, or mackerel. Kayaking and canoeing are popular ways to experience the waters, and nature trails scattered around the island allow visitors to explore the land and local wildlife.

What are the top things to do in Pine Island?

Randell Research Center

The Randell Research Center teaches visitors about Southwest Florida’s ecology, archaeology, and history through its museum, heritage trail, and 100-acre shellmound site. The Calusa Heritage Trail, well marked with interpretive signs, winds through nearly one mile of the mounds and canals of the Pineland archaeological site.

Museum of the Islands

This small museum features a look into the island’s rich history, with an extensive collection of vintage household artifacts, tools, generations of dolls, and newspaper articles. In addition to more than 1,700 shells, the nature collection features exhibits of the island’s plants and animals.

Cayo Costa State Park

While Pine Island is not known for its luxurious beaches, the barrier island of Cayo Costa, which is only accessible via boat, features nine miles of beautiful white-sand beaches and six miles of hiking and biking trails. During the 50-minute boat ride from Pine Island, you may even spot manatees and dolphins. Once you arrive, you can fish, snorkel, or watch for snowy plovers, tricolored herons, and other coastal birdlife.

Destinations to explore