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House holiday rentals in Pine Island

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Top-rated house rentals in Pine Island

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Hernando Beach
4.99 out of 5 average rating, 141 reviews

Firepit, Golf Cart, Kayaks, PedalBoat, Fish + more

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!!

Guest favourite
The main river scene showcases clear waters reflecting the surrounding greenery and homes. Palm trees line the banks, while various boats are moored nearby. The peaceful atmosphere invites exploration and relaxation along this beautiful stretch of the Weeki Wachee River.
Home in Weeki Wachee Gardens
4.95 out of 5 average rating, 129 reviews

MAiN RiVER: TiKi TROPiCAL Retreat Weeki Wachee Fl

Our cozy freshly remodeled home is located directly on the clear waters of the Weeki Wachee River filled with manatees, dolphins, and fish! Enjoy the waterfront patio while watching wildlife. Hop on the main river via our canoe, 8 kayaks, & paddle board for a quick row upriver to Roger's Park, Hospital Hole, or continue upriver for 6 beautiful miles of clear blue waters. The Gulf of America is just 1.5miles downriver. Bring your boat and tie off to our floating dock using the 9' boat ramp onsite

Top Guest favourite
A waterfront home is nestled among lush trees, reflecting beautifully on the calm canal waters. A large outdoor patio with shaded seating and a relaxing area is visible. Kayaks are stored nearby, enhancing the outdoor recreational appeal of the property.
Home in Homosassa
4.92 out of 5 average rating, 132 reviews

Private waterfront house with large outdoor bar

Enjoy waterfront views while sipping a cocktail at the giant outdoor bar. Two bedrooms offer queen beds in each and a pull-out queen-size sofa bed is in the living room. Close to popular Crumps Landing Restaurant. The Riverside Marina is nearby to launch your boat. There is ample parking for a boat trailer. Canal access to Halls River & Homosassa River for flats boats or pontoon boats only. Must be able to lower bimini to go under Halls River Bridge. Property includes three kayaks and one canoe.

Top Guest favourite
Home in Spring Hill
4.92 out of 5 average rating, 219 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.

Top Guest favourite
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
4.98 out of 5 average rating, 108 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!

Top Guest favourite
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
4.93 out of 5 average rating, 261 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.

Guest favourite
Two kayaks, one red and one orange, are anchored near a wooden dock by a turquoise building. Four blue Adirondack chairs are positioned on the patio, which overlooks a grassy area and a canal. Large windows allow natural light into the space.
Home in Spring Hill
4.93 out of 5 average rating, 191 reviews

Little Bohemia! Waterfront+kayaks+dock+tikitub

It is impossible not to fall in the love with the Weeki Wachee River - it's magical! The Little Bohemia Lodge is the perfect waterfront getaway - a perfect mix of retro and updated - you'll love the funky fun touches! You will probably find yourself spending most of your time out back watching manatees float by, grilling out, or sitting by the fire pit. Our outdoor Tiki Tub is perfect for hot baths after the cool river! The property comes with 2 tandem kayaks and 2 singles for your enjoyment.

Top Guest favourite
The image captures a vibrant outdoor area featuring a turquoise dock adorned with aquatic murals. Multiple kayaks and stand-up paddleboards are lined up on the grass. A hammock is suspended between palms, and a shed is visible in the background, surrounded by lush greenery.
Home in Spring Hill
4.99 out of 5 average rating, 104 reviews

Weeki Mermaid Retreat w/Kayaks SUPs Hammock Games

Discover Weeki Mermaid Retreat, a 3-bedroom, 2-bath oasis on the canals of the Weeki Wachee River. Enjoy the screened lanai, spacious deck, firepit, or launch kayaks and SUPs from the 75-ft dock. With two living areas, a full kitchen, and TVs in every room, there’s space for everyone. Family-friendly amenities include plenty of indoor and outdoor space, games, books, and a laundry room. Minutes from the river, attractions, and Weeki Wachee Springs. Your perfect Florida getaway awaits—book now!

Superhost
An open living space features a large dining table set for six, accompanied by decorative candles. A cozy seating area in the background includes a sofa and chairs, illuminated by natural light from multiple windows. The vaulted ceiling showcases exposed beams, enhancing the spacious feel.
Home in Hernando Beach
4.88 out of 5 average rating, 102 reviews

Waterfront A-Frame with Heated Pool, Dock, Kayaks

A Frame with private pool and private fishing/boat dock! Dive into relaxation in our screened-in pool, or fish from our private dock. Bring your boat and jetskis! Features: - Open floor plan - private full screened-in pool - oceanfront! fish right from your backyard! - grill, propane included - private fishing dock - boat slip - can accomodate boats up to 26' - 2 jet ski docks (BYO jetskis) - loaded kitchen - Complimentary coffee bar - kcups, sugars, creamers all included - 5 single kayaks

Guest favourite
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
4.83 out of 5 average rating, 129 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!

Top Guest favourite
A screened-in outdoor space features a large patio area with several lounge chairs and a dining table, all overlooking the river. A kayak is stored nearby, and a built-in ladder leads down to the water for convenient access.
Home in Weeki Wachee
4.97 out of 5 average rating, 181 reviews

Wasted Time on the Weeki Wachee - Kayak & Manatees

Manatees, fishing, kayaks, crystal clear water and the best location await you at "Wasted Time," our waterfront retreat on the beautiful Weeki Wachee river, minutes from Rogers Park. This 2/2 stilt home is comfortably furnished, sleeps 6 and comes complete with all the essentials and toys you could imagine, including boat dock. It features a large, screened in balcony patio overlooking the river, and an entire screened in entertaining space underneath the home. Direct access to the Gulf!

Top Guest favourite
A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.
Home in Odessa
4.96 out of 5 average rating, 123 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 beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

Popular amenities for Pine Island house rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Hernando County
  5. Pine Island
  6. House rentals