Vacation rentals in Pine Island

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.

Family · Location · Decor

Adult-Only Retreat w/ Pool & Spa | 18+, Private

🔒⛓️🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Value · Location · View

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.

Value · Family · Bathroom

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Value · Family · Parking

Eco-Luxurious Lakefront haven (Fire pit & Hot Tub)

Experience the perfect blend of an eco-friendly retreat and modern luxury of our lakefront container home. Nestled in the heart of nature, this stylish oasis promises an unforgettable experience where you can immerse yourself amidst the beauty of the countryside without sacrificing comfort. Plus, enjoy the opportunity to interact with our farm animals, adding a touch of rural charm to your agritourism escape. Also, feel free to check out my other listing, Casa de Elvira on my host profile.

Value · Family · Cleanliness

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.

Value · Family · Walkability

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.

Family · Location · Air conditioning

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.

Family · Value · Decor

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

Family · Location · Nearby

A Frame Stream Dream-Weeki Wachee

Escape to this charming A-Frame cedar cabin on the crystal-clear Weeki Wachee River. Spend your days kayaking, fishing, or relaxing on the private dock, then enjoy evenings with glowing underwater and LED dock lights. The cabin features 2 cozy cedar bedrooms, including a loft with a spiral staircase, plus a master suite with river views. Unwind in the spa-inspired bath with a waterfall faucet or the heated outdoor shower nestled in nature. Your unforgettable river getaway awaits.

Family · Location · Laundry

"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!

Value · Location · Condition

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.

Location · Family · Sleep quality