Holiday rentals with a kayak in Longboat Key

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Top-rated Accommodation with a Kayak in Longboat Key

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

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Top Guest favourite
A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.
Home in Terra Ceia
4.98 out of 5 average rating, 106 reviews

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

Top Guest favourite
A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.
Bungalow in Oldsmar
4.99 out of 5 average rating, 156 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
Bungalow in Indian Rocks Beach
4.96 out of 5 average rating, 198 reviews

Your private Waterfront Pool home!

See photos for City holiday event dates! Boat parade ! Street parade! Tree lighting! 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

Superhost
Home in Longboat Key
4.86 out of 5 average rating, 133 reviews

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Top Guest favourite
Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.
Cottage in Tampa
4.97 out of 5 average rating, 239 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, 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.

Top Guest favourite
An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.
Guesthouse in Laurel Park
4.97 out of 5 average rating, 499 reviews

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Top Guest favourite
Home in Apollo Beach
4.94 out of 5 average rating, 135 reviews

Waterfront Pool Oasis •Kayak, Games & Sunset Views

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

Top Guest favourite
Two green kayaks are positioned on a sandy area by the water's edge, framed by lush greenery and towering trees. The calm river reflects the surrounding foliage, creating a serene natural setting perfect for outdoor activities.
Home in Bradenton
5 out of 5 average rating, 107 reviews

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

Top Guest favourite
A shaded lounging area features a comfortable chair with a patterned cushion, facing a serene waterfront view. In the background, a dock extends into the calm water, surrounded by lush greenery and decorative plants.
Condo in Indian Rocks Beach
4.96 out of 5 average rating, 125 reviews

Villa Al Golfo Pristine Waterfront Oasis

Pristine villa in the lovely seaside Gulf town of Indian Rocks Beach, 2 short blocks to the beach & the Intracoastal in your backyard. All newly renovated, both inside and out, enjoy unobstructed water views, private entrance, personal patio & your own indoor/outdoor fireplace. When you aren't lounging outside or taking a glide on our paddle board, you'll love the gourmet kitchen, comfy living room, two large TV's, cable/wifi, luxe memory foam king bed & secured safe.

Guest favourite
Condo in Longboat Key
4.89 out of 5 average rating, 122 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Top Guest favourite
The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.
Home in Oldsmar
5 out of 5 average rating, 147 reviews

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Guest favourite
The exterior of a charming yellow bungalow is visible, featuring a covered patio area with potted plants. The entrance is accessed via a set of steps leading to the upper level, while brick pavers create a welcoming pathway.
Apartment in Bradenton Beach
4.87 out of 5 average rating, 405 reviews

Las Palmas Beach Rentals unit 2

Unit 2 Ground floor;800 sq ft; patio; limited beach view . Steps to the white sandy beach across the street Free parking to registered guest. Fully equipped kitchen with markets nearby, Restaurants and shopping, within walking or hop free trolly. Trolly stop nearby. Linens and basic supplies are included. Overnight guest are welcome to arrive early to adventure the island, stay parked until after sunset on departure day.

Popular amenities for Longboat Key kayak rentals

When is the best time to visit Longboat Key?

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Avg. price$634 AUD$558 AUD$597 AUD$664 AUD$524 AUD$525 AUD$403 AUD$340 AUD$343 AUD$524 AUD$589 AUD$709 AUD
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Quick stats about holiday rentals with a kayak in Longboat Key

  • Total holiday rentals

    Explore 50 holiday rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key holiday rentals start at $164 AUD per night before taxes and fees

  • Verified guest reviews

    Over 630 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Longboat Key holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Longboat Key rentals

  • 4.8 Average rating

    Longboat Key stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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