Vacation rentals in Pine Island

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.

4.98 out of 5 average rating, 115 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!

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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.

4.93 out of 5 average rating, 275 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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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.

4.93 out of 5 average rating, 351 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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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.

4.85 out of 5 average rating, 142 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!

LocationValueOutdoor spaces

4.99 out of 5 average rating, 176 reviews

Camper/RV in Spring Hill

Weeki Waterfront Airstream Glamping Experience

Nature Oasis 🤩 Glamping (Glamorous Camping) Experience in 25-foot Airstream Travel Trailer (RV) ✅ Lush forest views ✅ Tranquil waterfront location (paddle down the canal to the pristine Weeki Wachee River) ✅FREE amenities - hot tub, outdoor shower, firepit, griddle, bikes, yoga mats, kayaks, & stand-up paddle boards. SELF CARE UPGRADE is $100/person. It includes access to shared space: food forest, garden & waterfront wellness studio with experiences curated for you by your hostess.

ValueFamilyAmenities

4.91 out of 5 average rating, 139 reviews

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!

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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.

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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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.

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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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.

4.99 out of 5 average rating, 187 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!

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4.99 out of 5 average rating, 228 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.

LocationFamilyLaundry

4.98 out of 5 average rating, 205 reviews

A colorful cottage with a screened lanai rests along a serene river. Kayaks and a floating island are docked nearby, with reflections shimmering on the water. Lush greenery surrounds the property, creating a tranquil outdoor setting ideal for relaxation and recreation.

Cottage in Spring Hill

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

LocationFamilyHospitality

4.99 out of 5 average rating, 104 reviews

A large tree with branches adorned with string lights creates a warm ambiance in the outdoor area. Two wooden swings hang from the tree, surrounded by a ground covered in leaves, inviting relaxation in a serene, natural environment.

Tiny home in Spring Hill

Charm and comfy tiny house

Enjoy the lovely setting of this romantic💘 spot in nature. Comfort and charm await you in our tiny 🏡 , just 6 minutes from Weeki Wachee State Park. It is completely private, no shared spaces. Located in the middle of a spacious and fenced lot. Immerse yourself in the quiet atmosphere surrounding by nature. Enjoy a beautiful 🌅 under the shade and refreshing breeze of the 🌳 , a delicious ☕️ , a good 🍷 , a grill barbecue 🍗 or some marshmallows by the fire pit🔥.

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Popular amenities for Pine Island vacation rentals

Self check-in

Free parking on premises

Gym

BBQ grill

Laptop-friendly workspace

Pine Island house rentals

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.

4.97 out of 5 average rating, 126 reviews

Charming River House @ Weeki Wachee!

ValueLocationQuiet

5.0 out of 5 average rating, 19 reviews

"Come Sail Away" | Gulf Waterfront Stilt House

LocationFamilyCleanliness

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.

4.98 out of 5 average rating, 43 reviews

Island/Beachfront House - Majestic Sunsets

LocationFamilyAmenities

A serene waterfront view captures a vast expanse of calm water reflecting shades of blue, orange, and pink during sunset. The horizon is lined with soft clouds, enhancing the tranquil atmosphere of the beachfront. The sandy shore is visible in the foreground.

4.87 out of 5 average rating, 95 reviews

Pine Island Paradise in Weeki Wachee

LocationFamilyAir conditioning

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.

5.0 out of 5 average rating, 28 reviews

Pine Island Escape | Kayaks, Sand, Sunsets & Games

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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.

4.82 out of 5 average rating, 165 reviews

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

LocationValueAir conditioning

4.98 out of 5 average rating, 65 reviews

Nature Coast Retreats 3/2 Heated Pool, Gulf Access

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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.

4.98 out of 5 average rating, 43 reviews

Dockside Palms at Weeki Wachee with Kayaks!

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Other great vacation rentals in Pine Island

4.95 out of 5 average rating, 64 reviews

A wooden bench is positioned on the water's edge, facing a calm ocean. The sunset casts a warm glow over the vast water surface, reflecting hues of orange and blue. A small boat is visible in the distance, enjoying the tranquil scene.

Cottage in Spring Hill

Gulf Sunsets! Island Life but minutes to spring!

LocationFamilyIndoor spaces

4.96 out of 5 average rating, 49 reviews

Home in Hernando Beach

6BR Waterfront • Direct Gulf • Fire Pit • Biliards

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The back deck overlooks the serene waterway, framed by a palm tree. Comfortable seating arrangements are positioned for relaxation, while large windows provide views into the home. A sunset casts warm light, creating a peaceful setting along the water's edge.

4.85 out of 5 average rating, 59 reviews

EPIC Weeki Wachee home - Waterfront Rogers Park

LocationFamilyHospitality

4.88 out of 5 average rating, 16 reviews

Welcome to Weeki River Escape!

ValueFamilyAccess

4.95 out of 5 average rating, 79 reviews

A manatee is partially submerged in the water, surrounded by lush green vegetation. Its large body is visible among the water plants, with ripples indicating its movement. The interplay of light and shadow creates a serene atmosphere near the riverbank.

Tiny home in Spring Hill

Vintage tiny house on Weeki w/ kayaks and RV site

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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.

4.96 out of 5 average rating, 52 reviews

Weeki Wachee Riverfront Home with Amazing View!

LocationValueComfort

A simple façade of a cozy cottage is presented, featuring a white exterior with dark blue shutters. A welcoming front porch is equipped with potted plants, and a bright turquoise door stands out as the focal point. A gravel driveway leads up to the entrance.

5.0 out of 5 average rating, 18 reviews

The White House at Weeki Wachee Waterfront Cottage

LocationFamilyParking

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.