Holiday rentals with a kayak in Gulfport

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Top-rated rentals with kayak in Gulfport

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Superhost

Apartment in St. Petersburg

4.9 out of 5 average rating, 49 reviews

Designer Waterfront Luxury Condo in resort w/dock

Designer Oceanfront condo right on Boca Ciega Bay. 1B/1B Condo has a new sleeper sofa that can sleep your extra guests. NO resort fees!! The condo comes with FREE parking & FREE high speed WiFi. The resort has a HEATED POOL, hot tub, gym, and private fishing pier/dock. Two KAYAK’s included with condo rental, great for exploring the bay or fishing. The Kayaks can be launched from the private dock. This condo is also right across from the public boat ramp and only 5 minutes to the amazing BEACH.

Top guest favourite

Bungalow in Oldsmar

4.98 out of 5 average rating, 117 reviews

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

Top guest favourite

Home in Apollo Beach

4.98 out of 5 average rating, 139 reviews

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach

Apollo Beach Waterfront Pool Home, 4 bedroom-4 private baths & elevator. Theater room-murphy bed (5th bedroom). Game room- pool, air hockey.. Enjoy kayaks, paddle boards, fish at the dock, book a boat charter with owner. 3 restaurants, Bakery, Cigar Bar and Coffee/Ice Cream-walking distance. Apollo Beach - 1/2 mile away! Bahia Beach -2 restaurants and EG Simmons Beach - 20 min away. Bring your boat, dock at house, Apollo Beach Marina - 2 min. away. Animal-free home due to severe allergies.

Top guest favourite

Barn in Odessa

4.99 out of 5 average rating, 102 reviews

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.

Superhost

Home in Tampa

4.77 out of 5 average rating, 265 reviews

*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!

Superhost

Guest house in St. Petersburg

4.79 out of 5 average rating, 130 reviews

Guest House by the Lake

Large guest suite less than 10 minutes to both downtown St Pete and St Pete Beach. Walk out the back and you'll find yourself only a minute away from a large lake and a beautiful park. There is a golf range and practice green area located in the same park. The space is large and completely private. You will find everything you need - full bathroom, large closet, full table/desk, kitchenette, wifi/Netflix, yard/grill, etc. Also available to use: kayak, golf clubs, beach towels, fishing poles

Top guest favourite

Villa in Largo

4.97 out of 5 average rating, 133 reviews

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.

Guest favourite

Home in St. Petersburg

4.89 out of 5 average rating, 128 reviews

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.

Guest favourite

Townhouse in Pass-a-Grille Beach

4.89 out of 5 average rating, 225 reviews

Steps to Beach+bikes VaCay getaway on PaG island

Escape to charming Pass-a-Grille BeachHouse—your perfect beach getaway! Steps from Florida’s most beautiful beach, this cozy coastal retreat features hardwood floors, a beach wagon, smart TV's (also in bedroom) w/sports package, a sun patio, 2 bikes to explore. Soak up the old Florida charm and island vibes in this peaceful slice of paradise. This delightful one-bed -bath town-home style rental is situated steps away from the beautiful white sand beach that stretches for 7 miles.

Superhost

Houseboat in Clearwater Beach

4.86 out of 5 average rating, 100 reviews

Breathtaking Beachy Houseboat on Clearwater Island

🌊 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! 🌅🏝️🚤

Top guest favourite

Cottage in Tampa

4.97 out of 5 average rating, 206 reviews

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, 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. Pet fee $50.

Superhost

Flat in St. Petersburg

4.79 out of 5 average rating, 141 reviews

Sunshine St. Pete | 400ft² | bikes | kayak|netflix

♡ 400ft² private craftsman studio apartment on shared property ♡ ☞ Walk Score 82 (walk to cafes, dining, shopping..) ☞ Bike Score 75 (2 bikes provided) ☞ Memory foam mattress + sofa couch ☞ Fully equipped + stocked kitchen ☞ Free kayaks + beach gear ☞ Beach gear provided ☞ Onsite parking ☞ Swivel Smart TV w/ Netflix ☞ 214Mbps Wi-Fi ☞ AC & Heat 5 min → Salvador Dall Museum, Vinoy Park, St. Pete Pier 15 min → Airport & St Pete Beach