Vacation rentals with a kayak in Gulfport

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches. Happy holidays from our family to yours

Waterfront tiny in St Petersburg - The ‘V’

The ‘V’ is your perfect getaway to make fun memories. Note: You MUST have a 5 star rating on airbnb ! Take yourself back to the good old days of simplicity and relaxation. Paddle-board from your own private mangrove beach through the canals and to Tampa Bay. Experience dolphins swiming along side you, manatees feeding on sea grass or baby sharks out by the sandbar just 200 yards from the beach. The ‘V’ rests in a culd-de-sac in a quiet waterfront neighborhood just 10 minutes south of DT.

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.

Little Harbor Resort #109 Tampa Bay FL Beach, Pool

Little Harbor Resort is a paradise packed with amenities. Enjoy 2 pools, Jacuzzi, Beach on Tampa Bay (not Gulf), 2 restaurants, Tiki Bar, tennis, pickleball, basketball, playground, fishing charters, sightseeing cruises, and Freedom Boat Club. The Inn at Little Harbor River Delight Studio is a ground-floor, non-smoking studio which features a kitchenette, fridge, microwave, sink, in counter hotplate, dishwasher, coffee maker with two luxurious queen beds, and captivating island decor.

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.

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...

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.

Steps2Beach-Walk everywhere-Bikes & gear Included

Welcome to Paradise by the Sea 🌴 Your comfortable Florida beach cottage just steps from the sand in the heart of Pass-a-Grille. This charming island home offers the relaxed, old-Florida vibe guests love — with the convenience of being able to walk everywhere and rarely move the car. The beach is a quick, easy walk, and restaurants, coffee shops, ice cream, and the local market are all nearby. Guests often say it feels like settling into their home by the beach.

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!

Cottage near the sea

Welcome to our bungalow by the sea It is just 3 blocks away from waterfront Lassing Park, which can be enjoyed with kayaks and bicycles that are available for free, and perfect for exploring nearby downtown Saint Petersburg and the pier. The house is completely furnished with everything you need for a great stay. Charcoal grill, TV, coffee, Ironing board and iron , Wi-Fi Internet and Beach toys So kick back and relax and enjoy your stay.

Urban River Edge Loft w/Soaking Tub and King Bed

A spacious apartment with soaring ceilings encompassing all of the upper story of a historic bungalow, just steps from the Hillsborough River. You'll have your own deck overlooking the river, and be only 10 to 15 minutes from dwntwn Tampa, Amalie Arena, Armature Works, Ray James Stadium, Busch Gardens, & Cypress Point Beach -Complimentary Kayaks Included -Fast WiFi & Smart TV -Soaking Tub -Full Kitchen -Wood Burning Firepit

Waterfront Coastal 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 in a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 per pet.