
Vacation rentals in Pine Island
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Top-rated vacation rentals in Pine Island
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Sunshine Escape Hernando Beach Direct Gulf Access
🌞 Sunshine Escape – Luxury Waterfront Retreat in Hernando Beach Freshly renovated in 2024, this stylish canal-front escape offers direct Gulf access, a private dock, kayaks, paddleboards, bikes, firepit, and boutique coastal charm. Relax under the waterfront pergola with a drink in hand, explore the water by day, and unwind in comfort by night. Inside, you’ll find a bright living space, fully stocked kitchen, Smart TVs, and comfy bedrooms (King + Queen). Bring your boat, cast a line, or explore
LocationFamilyAccess
4.99 out of 5 average rating, 100 reviews
Newly Offered-Great Location - Sleeps 12 + Kayaks
Gulf Access +LOCATION!The whole group will enjoy easy access to everything from this centrally located place. See the drone photos on this ad. This home is ONLY a 5 min via kayaks to : The Main Weeki Wachee River + Rogers Park Playground + Rogers Park Beach + Rogers park Boat Ramp + Jon Boat Rentals + Upper Deck Resturaunt & located on a Deep- Water channel just a couple streets off Shole Line Blvd. Bicycles and Kayaks are included so you can experience the River Life to the fullest!
ValueLocationAccess
4.98 out of 5 average rating, 118 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.
ValueFamilySleep quality
4.93 out of 5 average rating, 276 reviews
Flip Flop River Stop
Throw on the flip flops and take it easy at this unique and tranquil getaway! Canal front dock with ladder to enjoy the visiting manatees or a quick paddle to the beautiful, clear Weeki Wachee river In the provided kayaks. Paddle to the springs or enjoy quick boat access to the Gulf for fishing or scalloping. Visit Pine Island, Weeki Wachee mermaids and Buccaneer Bay. One hour north of Tampa. Pets allowed. Must be declared! Max 2 (under 50 pounds each). **Monthly/weekly discounts on booking!
FamilyValueView
4.85 out of 5 average rating, 146 reviews
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.
LocationValueRiver
4.93 out of 5 average rating, 354 reviews
Tiki Paradise · Heated Pool · Waterfront · Kayaks
Heated screened-in pool, waterfront with private dock and direct Gulf access. Less than 7 minutes to the Weeki Wachee River — kayaking with manatees. Tiki hut at the water's edge for sunsets, fishing, and dolphin watching. Two floors, sleeps 10. - 3 bedrooms, 3 full bathrooms - 1 king, 2 queens, 2 bunk beds - Loaded coffee bar (Keurig, drip, Nespresso) - Sunroom - Heated screened pool, October 15 – June 30 - Private dock — bring your boat - 4 kayaks, fishing rods, fish cleaning station
ValueLocationAccess
4.94 out of 5 average rating, 110 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.
FamilyLocationBeach
4.99 out of 5 average rating, 228 reviews
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.
FamilyLocationWalkability
4.98 out of 5 average rating, 207 reviews
Charm and comfy tiny house
Enjoy the lovely setting of this romantic💘 spot in nature. Comfort and charm await you in our tiny 🏡 , just 6 minutes from Weeki Wachee State Park. It is completely private, no shared spaces. Located in the middle of a spacious and fenced lot. Immerse yourself in the quiet atmosphere surrounding by nature. Enjoy a beautiful 🌅 under the shade and refreshing breeze of the 🌳 , a delicious ☕️ , a good 🍷 , a grill barbecue 🍗 or some marshmallows by the fire pit🔥.
FamilyValueLayout
4.99 out of 5 average rating, 110 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 queen beds and bunks
LocationFamilyView
4.9 out of 5 average rating, 283 reviews
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.
FamilyValueKitchen
4.98 out of 5 average rating, 106 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.
LocationFamilyCheck-in
4.99 out of 5 average rating, 393 reviewsPopular amenities for Pine Island vacation rentals
Pine Island house rentals

PALM CREEK GETAWAY spring meets gulf+pool/spa
LocationFamilyAccess
4.86 out of 5 average rating, 126 reviews
A perfect Lake House get away
ValueFamilyHospitality
4.96 out of 5 average rating, 135 reviews
SEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!
FamilyLocationCheck-in
4.99 out of 5 average rating, 188 reviews
Angelita's Lake Home 3br3ba w/heated pool
FamilyLocationAmenities
4.99 out of 5 average rating, 105 reviews
"Come Sail Away" | Gulf Waterfront Stilt House
LocationFamilyCondition
5.0 out of 5 average rating, 21 reviews
Island/Beachfront House - Majestic Sunsets
LocationFamilyLong stay
4.98 out of 5 average rating, 44 reviews
Pine Island Escape | Kayaks, Sand, Sunsets & Games
FamilyLocationBeach
5.0 out of 5 average rating, 28 reviews
Pine Island Paradise in Weeki Wachee
ValueLocationWalkability
4.88 out of 5 average rating, 96 reviewsOther great vacation rentals in Pine Island

PARADISE POINT on Weeki Wachee (Boat Welcome)
LocationValueView
4.99 out of 5 average rating, 170 reviews
Gulf Sunsets! Island Life but minutes to spring!
FamilyLocationSleep quality
4.95 out of 5 average rating, 64 reviews
Nature Coast Retreats 3/2 Heated Pool, Gulf Access
FamilyValueWalkability
4.99 out of 5 average rating, 67 reviews
Sea Glass Cabin on the Weeki with kayaks
LocationGrillBackyard
4.92 out of 5 average rating, 13 reviews
Dockside Palms at Weeki Wachee with Kayaks!
FamilyLocationOutdoor spaces
4.96 out of 5 average rating, 46 reviews
Waterfront at Weeki Wachee
LocationFamilyOutdoor spaces
5.0 out of 5 average rating, 13 reviews
MainRiver-LG yard, 10Kayak, firepit,2 full kitchen
ValueFamilyGrill
4.86 out of 5 average rating, 91 reviews
6BR Waterfront • Direct Gulf • Fire Pit • Biliards
FamilyLocationAmenities
4.96 out of 5 average rating, 49 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
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- Weeki Wachee Springs
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Rainbow Springs State Park
- Amalie Arena
- Hard Rock Casino
- University of South Florida
- Dunedin Beach
- Epperson Lagoon
- MidFlorida Credit Union Amphitheatre
- Sand Key Beach
- Weeki Wachee Springs State Park
- Busch Gardens
- Splash Harbour Water Park
- Crystal River Archaeological State Park
- Fort Island Beach
- Three Sisters Springs
- Adventure Island
- World Equestrian Center
- Honeymoon Island State Park
- The University of Tampa
- Sunset Beach
- Fred Howard Park
- Tampa Convention Center





