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 Spring Hill

4.92 out of 5 average rating, 231 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.

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Top Guest favourite

Home in Hernando Beach

4.99 out of 5 average rating, 160 reviews

Fire pit, Golf Cart, Kayaks, PedalBoat, Fishing!

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!

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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, 272 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.

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Guest favourite

A spacious living area features a dark leather sofa and a coffee table on a textured area rug. Modern decor, including pendant lights and a fan, complements the rich green walls. Large windows provide natural light, while a dining area is visible in the background.

Home in Brooksville

4.98 out of 5 average rating, 103 reviews

South Brooksville Ave. Bungalow

Welcome to our historic home in Downtown Brooksville! This peaceful unit is located on one of the most historic streets in Brooksville, Florida! We are walking distance to local restaurants, shops, museums, concerts and trails! Sit, relax and enjoy the outdoors from one of the three decks or around the fire pit! Come and visit Florida's Nature Coast! We are near to Weeki Wachee River! Crystal River to visit the manatees and many other springs! Bike from here right to Withlacoochee State Trail!

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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, 111 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!

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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

4.93 out of 5 average rating, 349 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.

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Superhost

A serene view of the ocean at sunset, with vibrant hues of orange and pink reflected on the water's surface. Palm trees frame the image, while lush foliage adds to the natural setting, creating a peaceful coastal atmosphere.

Home in Weeki Wachee

4.83 out of 5 average rating, 163 reviews

Island House, Gulf Views Pine Isl., Tampa, Orlando

Private, island -house with breathtaking ocean views (+tons of space indoor & out to relax!) You'll have the privacy of the entire home, & screened in patio in this updated stilt house. Enjoy memory foam mattresses, stainless steel appliances, WiFi, Smart TV's - everything guests need to make your stay on this quaint island a cherished memory. Breathtaking Gulf views from nearly every window of the house! Watch dolphins frolic from your private deck. 10 min walk to the island beach-park.

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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

4.93 out of 5 average rating, 106 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

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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

4.86 out of 5 average rating, 125 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...

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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

4.9 out of 5 average rating, 282 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 queens and bunks. ASK ABOUT OUR JON BOAT RENTAL!

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Top Guest favourite

Home in Weeki Wachee

4.99 out of 5 average rating, 225 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.

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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

4.89 out of 5 average rating, 102 reviews

Weeki Wachee Hospital Hole Oasis

Take it easy at this unique and tranquil getaway. A beautiful 2-level home located in Weeki Wachee Gardens. 5 miles downstream from Weeki Wachee Springs State Park. This 900 sq. ft. home has a sleeping capacity for 4 people. Amenities include kayaks (4 singles.) 1 full bathroom, private laundry room, spacious seating, and sleeping accommodations. Smart tvs, Wi-Fi, 2nd story balcony, Bbq grill. Enjoy looking out to the main river from our balcony!

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