Holiday rentals with a kayak in Pinellas County

Cypress Lakes Barndominium

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

Steps to the Beach - Modern & Updated 2 BR Condo

AQUA BEACH CONDO - Only 90 steps from the beach, this beautifully updated and perfectly located beach condo offers you the very best of Indian Rocks Beach, a charming and intimate beach town located between Clearwater and St. Pete Beach. Two bedrooms with en-suite bathrooms and large walk-in closets, as well as the lofty living area and modern open kitchen will make you feel like at home. This condo is better equipped than your average vacation rental. Continue to read for more...

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

Renovated peaceful 2 Bed cottage with/hot tub.

Escape to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today and experience the tranquility of country living!

The Sand Dollar | Cozy Oasis with Hot Tub

Welcome to The Sand Dollar, a charming tiny house nestled among swaying palm trees, perfect for your beach getaway. 🐚🐚 Close to all local beaches, this cozy retreat offers everything you need for relaxation and adventure. Unwind in the hot tub or enjoy the serene atmosphere from the front porch. For the more adventurous, kayaks are available to explore the nearby waters. 🛶Experience the perfect blend of comfort and nature at The Sand Dollar. Book your stay today!

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Waterfront Courtyard Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more—all available right from the property! This is the perfect spot to make unforgettable beach memories! 🌅🏝️🚤