Vacation rentals with a kayak in Pinellas County

Charming Casita Near Two Downtowns & Beaches

This charming casita is a guest house located walking distance to downtown Dunedin, the Blue Jay's stadium, and short distance to downtown Clearwater and Clearwater beach. Steps to walking along the intracoastal for a walk or bike ride on the Pinellas trail. Conveniently acccessable to anything you may need for your stay. There is no shortage of things to do; shopping, water sports, fishing, biking, local parks, museums, cruises, etc.. Lots of variety for during the day and for night life. I’m

On the Beach "Little Peace of Heaven" Beach Condo

Spacious - Complete Renovation - Come see!! Our building is on an Island and on the beach! Our unit faces East or the Inter-coastal but the beach is just downstairs. Our 8 unit building is ‘On the beach. Downstairs we have a beautiful semi-private patio area surrounded by sea grape plants. We have a table and chairs, 16 beach chairs, kayaks and paddleboards, outside shower, gas grill, & a firepit for all to enjoy. Wonderful & quiet for families & couples. No smoking in the unit. No pets.

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

Enjoy best of Florida in this Updated and Newly Furnished 4 bed, 3 bath with PRIVATE SCREENED HEATED SALT WATER POOL and HOT TUB + FLORIDA ROOM+ GAME ROOM located short 3 miles to the beach. This home is in the quiet neighborhood, close to shopping, restaurants, grocery shops and beach. House accommodates up to 10 guests and has 1 KING BED and 3 QUEEN BEDS and 1 Bunk Bed for sleeping arrangements Both Living room and Florida room have Large Sectional Sofas Grill is available in the backyard

Cypress Lakes Barn Retreat

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.

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.

Charming 2BR Condo Near Ft. De Soto

Come enjoy your next vacation, holiday, or winter escape in Tierra Verde, Florida! Watch the sun rise over Boca Ciega bay from the balcony of this beautiful, updated first floor condo. This 2 bedroom/2 full bath unit has been thoughtfully designed and furnished with everything you need to enjoy an stress-free get-a-way that feels like home. This rental has an official Certificate of Use through Pinellas County as a Short Term Rental as well as a rental license through the state of Florida.

Tiny Oasis | Pool | Stocked Stay Near Indian Rocks

Welcome to The Tiny Oasis! A cozy boutique style retreat in Largo, FL, near Indian Rocks and Clearwater Beach that’s packed with luxury. Lounge by the plunge pool, fire up the Blackstone or enjoy an outdoor movie night. Unique touches and a 5-star experience prove that small spaces make big memories! Tap ‘Show More’ below! What’s There To Look Forward to? 👙Plunge Pool 🚿Outdoor Shower 🔴 Corn Hole ⛱️ Beach Gear 🍔Grill 🅿️ Private Parking 🍳Cook at Home 🧺 Your own private Washer/Dryer

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Ocean Dreaming: Waterfront Home with Heated Pool,

Waterfront home: pool, dock, golf cart, kayaks, paddle board. This home has a private, zero-entry heated pool and dock (tie up your own boat or daily/weekly rental). 6-seat golf cart, 2-paddle boards, 2-sea kayaks, 6-bicycles and more are included. Two master bedroom suites with water views and soaking tubs plus a third bedroom with custom King Bed and Twin bunk beds. Two living areas are also each furnished with a queen sofa sleeper to accommodate a total of 12 people.

Peaceful Pet friendly 2 BR cottage with hot tub.

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! Please note that the minimum age requirement to book is 23.

Your private Waterfront Pool home!

Heated pool option added January 2026!! Waterfront property, perfect getaway for quiet relaxation or family fun. Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with waterfront oasis all to yourself. Just step out the front door and walk 3 blocks to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about this host, our area, our style. BTR#1734 VRR#0422