Vacation rentals with a kayak in Tampa Bay

4.94 out of 5 average rating, 111 reviews

A serene backyard view showcases a sparkling pool with blue mosaic tiles, overlooking a calm canal. Palm trees frame the scene, and comfortable outdoor seating is arranged around the pool area, inviting relaxation in a peaceful atmosphere.

Home in Apollo Beach

Apollo Beach Waterfront Amazing PoolOasis w kayaks

Forget your worries in this spacious and serene space. You are invited to our private oasis waterfront home in Apollo Beach. Enjoy our backyard, from the outdoor living space, dining area, sun loungers, games, and the amazing pool overlooking the canal; Watch dolphins & manatees as you relax in the pool. Home equipped with a large kitchen, dining room, 2 bathrooms, 2 bedrooms and an additional living room with a closet and sleeping sofa that can be used as a private 3rd bedroom. LIC#DWE3913431

4.97 out of 5 average rating, 108 reviews

The exterior of the home is showcased beside a serene lake, framed by tall trees. A wooden deck is visible, adorned with ambient lighting, creating a welcoming space to relax. The expansive green lawn invites outdoor activities amidst nature.

Tiny home in Lutz

Lakefront Farm Tiny Home

This unique and off-the-beaten path home is a special opportunity for a short or long getaway. Located on a ski-sized lake, it is great for fishing, enjoying nature and farm animals and relaxing! This home is located on an active family farm, complete with cows, donkeys, mini goats and chickens. This certified green Tiny has two bedrooms, two lofted sleeping areas upstairs and one full bathroom with a stand-up shower. A nearby hammock completes the total rejuvenating experience. Feel far away!

4.98 out of 5 average rating, 117 reviews

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

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

4.79 out of 5 average rating, 296 reviews

Guest suite in Tampa

The Riverfront Suite at Casa del Alma

The riverfront suite @ Casa Del Soul has something for everyone. Whether you’re traveling for business, on vacation exploring Tampa Bay, or wanting to get out of the house for a weekend stay-cation look no more. Casa del Soul is centrally located in trendy/ eclectic neighborhood of Seminole Heights just minutes away from Ybor, Hard Rock, Downtown, South Tampa, Hyde Park , Lowry Park Zoo, Busch Gardens, Adventure Island, the Amphitheater, Arena, International Mall, Stadium, Restaurants & More.

4.99 out of 5 average rating, 102 reviews

A serene lakeside view is framed by tall trees with a lush green lawn in the foreground. A kayak is seen gliding across the calm water, reflecting the surrounding trees and blue sky. A covered dock is visible on the left, adding to the tranquil scenery.

Barn in Odessa

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.

The cabin is viewed from the water, featuring a stylish exterior and a spacious deck. A newly constructed dock extends over the calm canal waters, surrounded by lush greenery. A clear blue sky enhances the inviting natural setting.

4.77 out of 5 average rating, 264 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!

The image captures a serene waterfront view featuring a private dock leading down to the calm canal. A spacious backyard with lush green grass frames the caged pool area, while mature trees and tropical plants provide a tranquil setting.

4.81 out of 5 average rating, 118 reviews

Casa Paraiso- Pool Home with Canal Access

Waterfront Paradise by Tampa Bay! This centrally-located, newly updated 3-bed, 2-bath haven offers fantastic canal views.  Enjoy your private dock directly on the canal—perfect for docking your jet ski rental. Have a great fishing day, or take our kayaks to see manatees at Manatee Bend just down the canal! Take a dip in the pool for ultimate relaxation. - 10 min to beach - 8 min to airport - 8 min to mall - 25 min to bush gardens - 25 min to the aquarium - 20 min to the zoo

4.99 out of 5 average rating, 513 reviews

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

Tiny home in Tampa

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, koi pond, fire pit, hammocks, greenhouse, and even a bunny garden! Our goal is not just to offer you a place to stay but an experience you’ll cherish forever

4.74 out of 5 average rating, 105 reviews

The exterior of The Sand Dollar features a light-colored tiny house with white wood siding, a welcoming yellow front door, and a small set of wooden stairs. Flower pots with vibrant greenery frame the entrance, while hanging planters add a touch of charm.

Tiny home in Palm Harbor

The Sand Dollar | Cozy Oasis with Hot Tub

Welcome to The Sand Dollar, a charming tiny house nestled among swaying palm trees, perfect for your beach getaway. 🐚🐚 Close to all local beaches, this cozy retreat offers everything you need for relaxation and adventure. Unwind in the hot tub or enjoy the serene atmosphere from the front porch. For the more adventurous, kayaks are available to explore the nearby waters. 🛶Experience the perfect blend of comfort and nature at The Sand Dollar. Book your stay today!

Vacation home in Clearwater

4.9 out of 5 average rating, 105 reviews

Coastal Waterfront 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 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! 🌅🏝️🚤

4.98 out of 5 average rating, 205 reviews

Cottage in Tampa

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.

5 out of 5 average rating, 141 reviews

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

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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Bungalows

Intimate homes. inviting architecture

Villas

Luxurious estates for the ultimate escape

Popular amenities for Tampa Bay kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

A private heated pool is enclosed by a screen and features a spacious deck. Outdoor seating is available under an umbrella, while a stone outdoor kitchen is visible nearby. Lush greenery surrounds the area, promoting a serene environment for relaxation.

4.9 out of 5 average rating, 49 reviews

Lush Vacation Home with Pool

AbbyRating, 5 stars2 weeks ago

Our family of 4 enjoyed our stay. The house is updated with an open floor plan. TVs in each room, including the outside pool/kitchen area, beautiful kitchen. Highlights our family loved: private pool, nice lounge area, quiet community that was perfect for walking, close to amenities while being tucked away. Lissette was very responsive when we needed anything. And I loved the washer/dryer, which came in handy to keep up with pool towels.

Home in Indian Rocks Beach

5 out of 5 average rating, 25 reviews

Waterfront Oasis Pool, Spa, King Beds

SoniaRating, 5 stars1 week ago

It was my friends B’Day so decided to stay at this location because it was close to the beach, restaurants and the view was amazing. We even saw dolphins, plenty of fishes and a small shark. Adam was very responsive to any/all our concerns. Me and my friends definitely enjoyed our stay.

5 out of 5 average rating, 8 reviews

A heated saltwater pool is framed by a spacious patio, featuring several lounge chairs. A pink flamingo float adds a playful touch to the water. The view includes surrounding palm trees and a serene waterway, enhancing the outdoor relaxation space.

Home in New Port Richey

Waterfront Oasis

KenRating, 5 stars1 month ago

Had the pleasure of staying here for a few days. Nice quiet neighborhood and a very peaceful and relaxing time hanging out here. Would not hesitate to book again only next time would like to book a fishing trip on the Reel Anomaly docked out back. Just book it and enjoy.

4.95 out of 5 average rating, 128 reviews

The exterior of the historic home features white siding and a prominent metal roof. Large windows and an inviting front door are visible, framed by shade from mature trees. The landscaped front yard offers a sense of openness and charm.

Home in Bradenton

Historic Wares Creek 3 bedroom with dock access

AssemgulRating, 5 stars8 months ago

Clean and beautiful home, we really enjoyed our stay! The host Lisa was extremely helpful! Definitely recommended 👌🏼

Home in Indian Rocks Beach

A tranquil outdoor space features a circular hot tub adjacent to a rectangular swimming pool, both surrounded by brick pavers. The sunset casts soft colors across the water, with a view of boats docked nearby and the silhouette of trees in the distance.

5 out of 5 average rating, 169 reviews

Piece of paradise in Indian Rocks Beach.

KarleeRating, 5 stars3 days ago

Loved the house, location, pool, and hot tub! Short walk to the beach. Dinner was delivered our first night which was incredibly thoughtful and convenient after traveling all day! Overall a great experience! Would definitely recommend

4.88 out of 5 average rating, 49 reviews

Three kayaks are positioned on the grassy shore, facing a calm waterway lined with mangroves. The kayaks include a white single, a blue single, and a green double. Lush vegetation and a clear blue sky complete the serene coastal setting.

Home in Gibsonton

Kayaking at Bullfrog Creek

SuselRating, 5 stars2 weeks ago

Loved our stay. Beutiful cozy place. Catalina was great to communicate with and had no problem extending our checkout time. Would definitely consider the place again whenever in the area.

A serene outdoor space features a circular seating arrangement surrounding a fire pit, complemented by a hammock. Lush greenery frames the area, with views of the water and dock in the background, creating a tranquil atmosphere for relaxation.

4.91 out of 5 average rating, 181 reviews

Luxurious "Riverfront Oasis" - Waterfront w/pool

ThomasRating, 5 stars3 weeks ago

Very responsive and the house was great!

4.91 out of 5 average rating, 22 reviews

A cozy bedroom features a queen-sized bed with a light pink quilt and decorative pillows. An air conditioning unit is mounted above, while natural light filters through the windows adorned with white blinds. A mirror and a bedside table with a lamp complete the tranquil setting.

Home in Odessa

The Weekender- Lake Access, Bikes, Outdoor Living

PaulaRating, 5 stars1 month ago

Location was great. Everything was as perfect as the listing showed. Host checked in to make sure everything was going good. Would definitely stay again.

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Cottage rentals with a kayak

Cottage in St. Pete Beach

A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

4.81 out of 5 average rating, 278 reviews

Sunny PaG Island rental w/bikes-just steps2beach

JonathanRating, 5 stars2 weeks ago

Nice place super close to the beach that had everything we needed! Made it a very enjoyable stay. Lisa was easy to communicate with and provided great directions on everything. We had a great time.

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

Cottage in Clearwater

4.77 out of 5 average rating, 149 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

MarkRating, 5 stars2 weeks ago

Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!

5 out of 5 average rating, 8 reviews

A modern kitchen features white shiplap walls and an island with a light marble countertop. Four wooden bar stools with caned backs are positioned at the island. Pendant lights with woven shades hang above, and silver appliances are visible in the background.

Cottage in Holmes Beach

Anna Maria Cottage w/Golf Cart

SarahRating, 5 stars2 weeks ago

My son and I had a wonderful stay at this cute little cottage. Everything was clean and well-decorated, and we had everything we needed in the kitchen. We loved having the golf cart to run around in! The host also provided beach chairs and a kayak to use, which was very handy. The area is pleasant, situated in a quiet neighborhood with public tennis and basketball courts across the street. Anna Maria is a happy little island, with a lot of good food and entertainment, and a number of beach areas to choose from. Lynda was very responsive to any questions we had, and provided a lot of easy -to-follow instructions for the house, as well as lots of helpful tips about the area. We will definitely be back!

4.91 out of 5 average rating, 117 reviews

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

Little Manatee River Cottage

CharlesRating, 5 stars1 month ago

Had a great stay ! Fishing was fun and right across the street Would stay again for sure !

4.94 out of 5 average rating, 125 reviews

Cottage in Tampa

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

HanselRating, 5 stars1 month ago

Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Can’t go wrong.

5 out of 5 average rating, 31 reviews

Cottage in Bradenton

2/2 Charming Riverfront Cottage w Deck & Kayaks

KellyRating, 5 stars1 week ago

We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

Cottage in Indian Rocks Beach

A bright and airy living area features a comfortable sofa adorned with striped and coral-colored pillows. Two leather armchairs provide additional seating, positioned around a round wooden coffee table. A large flat-screen TV is mounted on a white shiplap wall, with soft lighting enhancing the welcoming atmosphere.

4.95 out of 5 average rating, 19 reviews

Sandy/Salty- Sleep 16 - 2 homes connected by yards

LexiRating, 5 stars2 months ago

Great gathering place for an extended family to get together. Very short walk to a stunning beach Great for kids. Perfectly located next to a park as well which was great.

4.93 out of 5 average rating, 86 reviews

A cozy living space features a dark leather couch and a decorative wooden coffee table. Natural light streams through large windows adorned with blue patterned curtains. A flat-screen TV is mounted on the wall, and a wooden cabinet displays nautical-themed decor.

Cottage in Riverview

Alafia River Cottage

AngelaRating, 5 stars4 weeks ago

This place was wonderful ! Martha was great and very responsive anytime ! Quiet and peaceful and very charming cottage ! Will definitely be returning

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Cabin rentals with a kayak

4.92 out of 5 average rating, 13 reviews

The exterior of the cabin is illuminated by string lights, creating a welcoming ambiance. A patio area features seating and a table, while a grill is positioned nearby. A nearby flag adds a touch of character, and greenery can be seen around the space.

Cabin in Port Richey

Cotee River Guest Cabin

MarkRating, 5 stars2 months ago

great place for the money..very peaceful.

4.86 out of 5 average rating, 22 reviews

A spacious deck is shown with wooden flooring, surrounded by tall trees draped in Spanish moss. A serene lake is visible in the background, reflecting sunlight through the foliage. The scene provides a tranquil setting for outdoor relaxation near the water's edge.

Cabin in Odessa

LakeHouse Cabin Getaway

AlejandroRating, 5 stars2 months ago

Cozy and beautiful place, the views of the lake are amazing, can’t wait to come back

4.92 out of 5 average rating, 12 reviews

A private balcony offers serene river views, framed by lush foliage and a palm tree. Two cushioned chairs sit beside a small glass table, providing a cozy space for relaxation while enjoying the surroundings under a partly cloudy sky.

Cabin in Ruskin

River Cabin Million Dollar View!

BobbyRating, 5 stars2 months ago

Very nice and peaceful place.. Will definitely be back again.Awesome view!!! Cozy and clean.