
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
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
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
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!
4.91 out of 5 average rating, 140 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
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 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.
4.99 out of 5 average rating, 393 reviews
Charming River House @ Weeki Wachee!
Located in Weeki Wachee Gardens, FL launch right off the back deck for a short paddle to the crystal clear Weeki Wachee River. Enjoy the area by using one of our provided 7 adult & 2 youth kayaks, 1 paddle board, 1 canoe and life jackets of all sizes. Swim with manatees in the backyard canal or fish right from our private dock where you can also tie up your boat or enjoy a short boat ride to the Gulf of Mexico.
4.97 out of 5 average rating, 129 reviewsPopular amenities for house rentals in Pine Island
House rentals with a pool

Tiki Paradise · Heated Pool · Waterfront · Kayaks
4.94 out of 5 average rating, 110 reviews
TreeHouse, Swings, HotTub, HeatedPool, ClearSpring
4.97 out of 5 average rating, 111 reviews
Angelita's Lake Home 3br3ba w/heated pool
4.99 out of 5 average rating, 103 reviews
Weeki Wachee Springs heated pool home retreat
4.96 out of 5 average rating, 162 reviews
Spring Hill, Florida Quaint Paradise
4.94 out of 5 average rating, 144 reviews
3BR Roman Oasis: Caesar's Place + Heated Pool
4.94 out of 5 average rating, 144 reviews
Waterfront A-Frame with Heated Pool, Dock, Kayaks
4.89 out of 5 average rating, 111 reviews
Ranch Pool Resort with Horses jacuzzi nearby park
4.89 out of 5 average rating, 184 reviewsWeekly house rentals

River Beach Retreat | Tiki Bar, Hot Tub & Kayaks
4.93 out of 5 average rating, 148 reviews
SEA COW RIVER HOUSE - KAYAKS AND CANOES INCLUDED!
4.99 out of 5 average rating, 188 reviews
Hot Tub, Waterfront, Private Dock, Pet, 4 Kayaks
4.98 out of 5 average rating, 105 reviews
Weeki Wachee Hospital Hole Oasis
4.89 out of 5 average rating, 104 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
4.87 out of 5 average rating, 95 reviewsPrivate house rentals

Dockside Palms at Weeki Wachee with Kayaks!
4.96 out of 5 average rating, 46 reviews
Main River: Hot Tub, Jon boat, hot tub
4.81 out of 5 average rating, 53 reviews
6BR Waterfront • Direct Gulf • Fire Pit • Biliards
4.96 out of 5 average rating, 49 reviews
MainRiver-LG yard, 10Kayak, firepit,2 full kitchen
4.86 out of 5 average rating, 91 reviews
Weeki Wachee River | Clear Kayak | Waterfront
5.0 out of 5 average rating, 27 reviews
Luxe Lagoon House Weeki Wachee (sleeps 12)
5.0 out of 5 average rating, 55 reviews
Welcome to Weeki River Escape!
4.88 out of 5 average rating, 17 reviews
Private Pool, Sauna & Game Room Oasis
5.0 out of 5 average rating, 5 reviewsDestinations to explore
- Miami Holiday rentals
- Four Corners Holiday rentals
- 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





