
House holiday rentals in Pine Island
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Top-rated house rentals in Pine Island
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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!
4.98 out of 5 average rating, 118 reviews
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
4.99 out of 5 average rating, 100 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.
4.93 out of 5 average rating, 276 reviews
A perfect Lake House get away
Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team
4.96 out of 5 average rating, 135 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!
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.
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
4.94 out of 5 average rating, 110 reviews
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...
4.86 out of 5 average rating, 126 reviews
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!
4.99 out of 5 average rating, 188 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.
4.99 out of 5 average rating, 228 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
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.
4.98 out of 5 average rating, 106 reviewsPopular amenities for house rentals in Pine Island
House rentals with a pool

Waterfront home heated pool+jacuzzi+game room+golf
4.91 out of 5 average rating, 142 reviews
Angelita's Lake Home 3br3ba w/heated pool
4.99 out of 5 average rating, 105 reviews
TreeHouse, Swings, HotTub, HeatedPool, ClearSpring
4.97 out of 5 average rating, 111 reviews
Saltwater Pool • Kayaks • Pedal boat + more!
4.97 out of 5 average rating, 148 reviews
3BR Roman Oasis: Caesar's Place + Heated Pool
4.94 out of 5 average rating, 144 reviews
Ranch Pool Resort with Horses jacuzzi nearby park
4.89 out of 5 average rating, 184 reviews
Tropical Oasis | Heated Pool & 3 Min Sister Spring
4.87 out of 5 average rating, 281 reviews
Waterfront A-Frame with Heated Pool, Dock, Kayaks
4.89 out of 5 average rating, 111 reviewsWeekly house rentals

Weeki Wachee Hospital Hole Oasis
4.89 out of 5 average rating, 104 reviews
Charming River House @ Weeki Wachee!
4.97 out of 5 average rating, 129 reviews
"Come Sail Away" | Gulf Waterfront Stilt House
5.0 out of 5 average rating, 21 reviews
Island/Beachfront House - Majestic Sunsets
4.98 out of 5 average rating, 44 reviews
Pine Island Escape | Kayaks, Sand, Sunsets & Games
5.0 out of 5 average rating, 28 reviews
Pine Island Paradise in Weeki Wachee
4.88 out of 5 average rating, 96 reviews
Island House, Gulf Views Pine Isl., Tampa, Orlando
4.82 out of 5 average rating, 165 reviews
Bamboo Bungalow. Steps to a Gulf sunset & fishing
4.82 out of 5 average rating, 39 reviewsPrivate house rentals

Upriver Waterfront: Kayaks & Movie Theater
5.0 out of 5 average rating, 76 reviews
Charley’s On Main River-Clear H2O, Kayak, Preserve
4.96 out of 5 average rating, 90 reviews
Waterfront at Weeki Wachee
5.0 out of 5 average rating, 13 reviews
Dockside Palms at Weeki Wachee with Kayaks!
4.96 out of 5 average rating, 46 reviews
6BR Waterfront • Direct Gulf • Fire Pit • Biliards
4.96 out of 5 average rating, 49 reviews
Welcome to Weeki River Escape!
4.88 out of 5 average rating, 17 reviews
Weeki Wachee Riverfront Home with Amazing View!
4.96 out of 5 average rating, 53 reviews
Mermaid Life On the Main River with kayaks
4.95 out of 5 average rating, 40 reviewsDestinations to explore
- Miami Holiday rentals
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- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Hilton Head Island Holiday rentals
- 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





