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House holiday rentals in Pine Island

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Top-rated house rentals in Pine Island

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Top guest favourite
A vibrant sunset paints the sky over the tranquil river. An Adirondack chair is positioned on a concrete pad, facing the water. Kayaks are anchored nearby, surrounded by lush greenery and reflections on the calm surface. The inviting scene captures the natural beauty of the river setting.
Home in Weeki Wachee Gardens

Bigfoot's Bungalow: 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. Roger's Park is a quick row up river, and just around the corner from that is Hospital Hole where manatees love to congregate. Our house is one of the newer homes on the river with balconies galore and can accommodate your large group with 4 spacious bedrooms and an elevator (only for elderly/handicapped use)! Bring your boat to tie up or use the 7 single kayaks and two 3 person canoes provided

4.95 out of 5 average rating, 207 reviews
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

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
Top guest favourite
Home in Hernando Beach

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
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

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
Guest favourite
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.

4.93 out of 5 average rating, 354 reviews
Top 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

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
Top guest favourite
A spacious patio area surrounds the heated pool, featuring a table with an umbrella and several comfortable chairs. The screened enclosure allows for unobstructed views of the clear blue water and is complemented by a grill station nearby.
Home in Hernando Beach

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

4.93 out of 5 average rating, 111 reviews
Guest favourite
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!

4.91 out of 5 average rating, 142 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...

4.86 out of 5 average rating, 126 reviews
Top guest favourite
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!

4.99 out of 5 average rating, 188 reviews
Top guest favourite
Home in Weeki Wachee

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
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 queen beds and bunks

4.9 out of 5 average rating, 283 reviews

Popular amenities for house rentals in Pine Island

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
Home in Hernando Beach

Saltwater Pool • Kayaks • Pedal boat + more!

4.97 out of 5 average rating, 148 reviews
Guest favourite
A spacious outdoor area features a hot tub with bubbling water, surrounded by a screened patio. A swimming pool gleams in the sunlight, while a vibrant tree house play area with a slide and swing set adds a colorful touch to the yard.
Home in Spring Hill

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring

4.97 out of 5 average rating, 111 reviews
Top guest favourite
A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.
Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

4.99 out of 5 average rating, 105 reviews
Top guest favourite
Home in Spring Hill

Spring Hill, Florida Quaint Paradise

4.94 out of 5 average rating, 144 reviews
Top guest favourite
An outdoor screened area features a private heated pool surrounded by a spacious deck. Two lounge chairs are positioned nearby, with a barbecue grill present for outdoor cooking. A dining set with multiple chairs is also visible under a covered patio, providing shade and comfort.
Home in Spring Hill

Weeki Wachee Springs heated pool home retreat

4.96 out of 5 average rating, 162 reviews
Top guest favourite
Home in Spring Hill

3BR Roman Oasis: Caesar's Place + Heated Pool

4.94 out of 5 average rating, 144 reviews
Guest favourite
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

Waterfront A-Frame with Heated Pool, Dock, Kayaks

4.89 out of 5 average rating, 111 reviews
Superhost
Home in Crystal River

Tropical Oasis | Heated Pool & 3 Min Sister Spring

4.87 out of 5 average rating, 281 reviews

Weekly house rentals

Guest favourite
Home in Spring Hill

River Beach Retreat: Tiki Bar, Hot Tub, Kayaks&BBQ

4.93 out of 5 average rating, 148 reviews
Top guest favourite
Home in Spring Hill

Weeki Mermaid Retreat w/Kayaks SUPs Hammock Games

4.99 out of 5 average rating, 115 reviews
Top guest favourite
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!

4.97 out of 5 average rating, 129 reviews
Guest favourite
A serene outdoor space features four turquoise chairs arranged around a central fire pit. The area is paved with stones and overlooks a calm river, with greenery and a covered dock visible in the background.
Home in Spring Hill

Weeki Wachee Hospital Hole Oasis

4.89 out of 5 average rating, 104 reviews
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

Little Bohemia! Waterfront+kayaks+dock+tikitub

4.93 out of 5 average rating, 207 reviews
Top guest favourite
Home in Spring Hill

"Come Sail Away" | Gulf Waterfront Stilt House

5.0 out of 5 average rating, 21 reviews
Top guest favourite
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

4.98 out of 5 average rating, 44 reviews
Top guest favourite
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

5.0 out of 5 average rating, 28 reviews

Private house rentals

Top guest favourite
Home in Spring Hill

Michele's Spring House

5.0 out of 5 average rating, 42 reviews
Top guest favourite
A modern two-story home with large windows is surrounded by lush greenery. A wooden deck, accessible by steps, extends from the house. A stone pathway leads through the manicured lawn, offering inviting views of the exterior landscaping and surrounding trees.
Home in Spring Hill

Luxe Lagoon House Weeki Wachee (sleeps 12)

5.0 out of 5 average rating, 55 reviews
Top guest favourite
The backyard features a vibrant landscape with lush greenery surrounding the canal. A wooden dock is visible, along with kayaks ready for use. Multiple seating arrangements, including picnic tables and colorful chairs, create inviting outdoor spaces for relaxation and gatherings.
Home in Spring Hill

Upriver Waterfront: Kayaks & Movie Theater

5.0 out of 5 average rating, 76 reviews
Guest favourite
Home in Spring Hill

Waterfront at Weeki Wachee

5.0 out of 5 average rating, 13 reviews
Guest favourite
The three-story home is situated along a river, featuring a spacious deck with seating and an expansive tree for shade. A concrete walkway leads to a floating dock, providing access to the water, while colorful plants and decor add vibrancy to the outdoor space.
Home in Spring Hill

Weeki Wachee Riverfront Home with Amazing View!

4.96 out of 5 average rating, 53 reviews
Guest favourite
Home in Spring Hill

Main River: Hot Tub, Jon boat, hot tub

4.81 out of 5 average rating, 53 reviews
Top guest favourite
An expansive wooden dock extends towards the river, bordered by lush greenery. Colorful kayaks are arranged on the dock, alongside bright lounge chairs. A shaded area beneath a large tree offers a relaxing space, connecting the home and the serene water.
Home in Spring Hill

Charley’s On Main River-Clear H2O, Kayak, Preserve

4.96 out of 5 average rating, 90 reviews
Guest favourite
Three kayaks in vibrant colors are positioned on a stone patio overlooking a calm canal. Palm trees frame the scene, and a sunset casts a warm glow over the water. Nearby seating areas are visible, surrounded by lush greenery and inviting outdoor spaces.
Home in Spring Hill

Dockside Palms at Weeki Wachee with Kayaks!

4.96 out of 5 average rating, 46 reviews

Destinations to explore