Holiday rentals with a kayak in Clearwater Beach

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

Location · Outdoor spaces · Nearby

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

Outdoor spaces · Location · Decor

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

Outdoor spaces · Location · Cleanliness

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.

Outdoor spaces · Location · Comfort

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Location · Value · Amenities

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Value · Location · Air conditioning

Steps from the Sand - Clean, Stylish 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...

Location · Outdoor spaces · Biking

Cozy AF Tiny-House Oasis

Awarded a *Unique Stay* by Airbnb, welcome to the **Cozy AF Tiny-House Oasis**, a rustic tiny home that started its journey as a world-traveling storage container. Now transformed into a charming cottage, it’s filled with unique and fun details waiting to be discovered. Enjoy the entire backyard, complete with a hot tub, pond, fire pit, hammocks, greenhouse, and we even have rabbits! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

Location · Value · Nearby

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.

Value · Location · Pool

Sunrise Suite | Hot Tub | Kayak | SUP | Waterfront

☀ Bay View Duplex ☀ Shared Hot Tub ☀ Dock with Stand-up Paddle boards, Kayaks, Bikes ☀ Only 3 blocks to the sugary sands of Indian Rocks Beach ☀ Duplex- book independently or together ☀ Blackstone, 6 burner Charbroil Grill ☀ 10 Foot Custom Wood Bar w/ Jenga, Giant Connect 4, Corn Hole, Ringtoss ☀ Beach Wagons, Speaker, Zero Gravity beach chairs, beach towels, cooler ☀ Amazon Dot with Unlimited Amazon Music

Outdoor spaces · Value · Backyard

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

Outdoor spaces · Location · TV

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Location · Value · Indoor spaces