Holiday rentals with a kayak in Gulfport

Townhouse in Redington Beach

A bright living area features comfortable white seating arranged around a wooden coffee table. Built-in shelves display books and decorative items. A flat-screen TV is mounted on a shiplap wall, while a dining area is visible in the background, showcasing a rustic table and modern fixtures.

Modern Townhouse right across beach! Table tennis

3 Bedroom/2.5 Bath modern townhome across street from beach, 2 large balconies off of living room and master bedroom. Lush landscaping. Enjoy meals in the beautiful dining area. Full equipped kitchen! Parking garage 1 car and driveway parking available. Sleeps 10. We rent all year round due to beautiful Florida weather. Walking distance to beach, restaurants, parks, basketball court, volleyball. Close to Johns Pass, 1 mile - Indian Rocks Beach. Tampa, Clearwater and St. Pete are a short drive.

4.92 out of 5 average rating, 132 reviews

5.0 out of 5 average rating, 17 reviews

Home in Gulfport

Sunset Cove Bungalow

Kick back & relax in this calm, stylish waterfront bungalow. Located on Boca Ciega Bay in the quirky town of Gulfport, this special little house is the perfect getaway. Bikes, kayaks, paddleboard, beach chairs, umbrellas are all in the boathouse, ready for your daily adventures! Fully loaded kitchen & large dining room make meals at home easy, but Gulfport also has a wide array of dining options including seafood, Italian, French, Greek & more. (Adults only please as we are waterfront w/ a pool)

An outdoor living space features string lights overhead, illuminating a comfortable sectional seating area and a fire pit. A large bar area with stools is seen alongside a mounted television, creating an inviting atmosphere for entertainment and relaxation.

4.96 out of 5 average rating, 48 reviews

Central Bungalow Near DTSP with Swim Spa!

Vacation like a local at this centrally located bungalow style residence. This 3BR 2 Bath home is set to entertain our guests. Indoor living space Includes two sitting areas, fireplace and workstation. The dining room and kitchen welcomes you home with all the amenities you need to keep everyone happy. For our outdoor lovers, we welcome you to the tavern. This fully functional outdoor living space includes a grill, tv, sectional seating, full size bar. Be our guest and enjoy St Pete like a local

Apartment in Tierra Verde

The image displays a serene pool area with clear water reflecting sunlight. Lush greenery and palm trees frame the space, while a view of the ocean is visible in the background. Sun loungers are arranged around the pool, inviting relaxation.

Charming 2BR Condo Near Ft. De Soto

Come enjoy your next vacation, holiday, or winter escape in Tierra Verde, Florida! Watch the sun rise over Boca Ciega bay from the balcony of this beautiful, updated first floor condo. This 2 bedroom/2 full bath unit has been thoughtfully designed and furnished with everything you need to enjoy an stress-free get-a-way that feels like home. This rental has an official Certificate of Use through Pinellas County as a Short Term Rental as well as a rental license through the state of Florida.

4.91 out of 5 average rating, 210 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

4.91 out of 5 average rating, 190 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.

A spacious living area features a large sectional sofa, complemented by decorative tables and potted plants. Expansive windows provide views of the water and outdoor seating, while natural light brightens the modern, open layout.

5.0 out of 5 average rating, 100 reviews

Walk to Beach! Waterfront Lux Retreat w/Kayaks

As seen on the Emmy award-winning show, Staycation. Experience the serene beauty of a waterfront Indian Rocks Beach Home. Wake up to breathtaking views of the water, right from your window. Enjoy the luxury of kayaking or fishing off your private boat dock. Spend evenings gathered around the fire pit or showcase your culinary skills with our grill. Just a 7-minute walk and you'll find yourself on the pristine white sands of Indian Rocks Beach. Kayaks and boat lift available.

4.96 out of 5 average rating, 45 reviews

Home in Coquina Key

Waterfront pool home w/dock, firepit, kayaks

Waterfront pool home minutes from downtown St. Pete. Gorgeous water views from all living areas, brand new pool, screened-in porch and large deck area for waterfront relaxing. Dolphins, manatees and gorgeous sunsets await you at this modern and perfectly located vacation oasis. This home offers easy access to award-winning restaurants, lively bars, a thriving arts scene, and many amazing beaches. Public boat launch, basketball and pickleball courts just minutes away.

An outdoor space features a stylish lounge area with two chaise lounges placed on a wooden deck. A large umbrella offers shade over a table. The backdrop includes a resort-style pool, surrounded by palm trees, as a sunset paints the sky in soft hues.

5.0 out of 5 average rating, 37 reviews

The Olivia

Modern organic entire home with elevated amenities, a resort-style pool and private outdoor oasis. This luxurious home is perfect for resting, retreating and entertaining. Walking distance to the best local produce market, restaurants and shops for everything you need and only a 9 minute drive to the most famous Upham & St. Pete Beach. This tropical paradise is truly one of a kind with "low-tox" living amenities we've consciously curated with your well-being mind!

Cottage in Pass-a-Grille Beach

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.

4.89 out of 5 average rating, 193 reviews

Apartment in Treasure Island

SolMate 2/2, kayaks, beach, views, boat slip

Newly renovated beach home, bright and beautifully appointed 2 bed/2 bath second floor condo with balcony overlooking Boca Ciega Bay. Modern beach decor. Only few steps to Treasure Island’s white sandy BEACH. Incredible water views from every window. 3 KAYAKS available (must sign waiver). Fun activities including ping pong, corn hole, etc. in common area. Only 6 units on property. Featured on HGTV Beachfront Bargain Hunt (Season 27 Episode 10).

4.93 out of 5 average rating, 147 reviews

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

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

4.97 out of 5 average rating, 234 reviews

4.76 out of 5 average rating, 218 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

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!

Popular amenities for kayak rentals in Gulfport

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.98 out of 5 average rating, 137 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Town 'n' Country

Canal-front Sanctuary | Manatees, Pool, Hot Tub

4.93 out of 5 average rating, 102 reviews

Salty Air Retreat - Hot Tub | Walk to the Beach!

4.97 out of 5 average rating, 145 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

4.89 out of 5 average rating, 165 reviews

Luxury waterfront | Walk to beach • Private dock

4.83 out of 5 average rating, 136 reviews

A spacious pool area features a heated saltwater pool and a hot tub surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a grill is visible, providing an inviting outdoor space. The screened enclosure offers a sense of privacy and comfort.

Home in Belleair Bluffs

Hidden Oasis W Screened Heated Salt Pool / Hot Tub

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.

5.0 out of 5 average rating, 200 reviews

Piece of paradise in Indian Rocks Beach.

4.86 out of 5 average rating, 118 reviews

Aerial view of a beach with soft white sand and turquoise waters, showcasing several beachgoers relaxing under the sun. Residential buildings are visible in the background, indicating a serene coastal community. The shoreline curves gently, inviting exploration and enjoyment of the beach.

Home in Indian Shores

Fabulous Beach House 3BR, Bikes-Kayaks-SUP

5.0 out of 5 average rating, 15 reviews

Large Waterfront Estate w/pool, hot tub, and dock!

Other holiday rentals with a kayak

Apartment in Treasure Island

Beachside Retreat: 2BR Condo, Pool & Bay Views

4.82 out of 5 average rating, 11 reviews

Apartment in Isla del Sol

St. Pete Isla Vista Verde North Mirada Townhome 3/2

4.53 out of 5 average rating, 19 reviews

Apartment in Isla del Sol

Top Floor Waterfront Escape | Spectacular Views

4.92 out of 5 average rating, 13 reviews

Apartment in Treasure Island

A serene waterfront scene showcases clear blue waters dotted with wooden docks. A grassy area with palm trees and outdoor seating highlights the tranquil setting, inviting relaxation. The sky is bright with scattered clouds, emphasizing the beauty of this picturesque location.

Treasure Island Waterfront Condo • Sunrise Views

4.93 out of 5 average rating, 29 reviews

4.92 out of 5 average rating, 13 reviews

Home in St. Pete Beach

Summer Bayfront + Guest Suite | Pool/Spa/Boat Lift

5.0 out of 5 average rating, 7 reviews

Home in Redington Beach

Intercoastal 4 Bed 3 Bath Pool Home Mins to Beach

4.9 out of 5 average rating, 10 reviews

Home in Redington Beach

Redington Beach near beach on ICW w/pool & dock