Holiday rentals with a kayak near Bean Point Beach

4.98 out of 5 average rating, 124 reviews

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

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.

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 123 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

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

4.91 out of 5 average rating, 191 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.

Home in St. Petersburg

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 private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 210 reviews

Private 30’ Pool &Boat Dock & Only Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

4.88 out of 5 average rating, 207 reviews

A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.

Bungalow in Anna Maria

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Apartment in Longboat Key

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, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

4.88 out of 5 average rating, 139 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!

4.96 out of 5 average rating, 129 reviews

Two bright turquoise adirondack chairs are positioned on a pebbled shoreline, facing a calm canal. Lush palm trees and greenery surround the area, while distant houses line the opposite bank under a clear blue sky.

Home in Bradenton Beach

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

4.86 out of 5 average rating, 439 reviews

Flat in Bradenton Beach

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.

4.82 out of 5 average rating, 119 reviews

Home in Bradenton Beach

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Gulf-views inside home. • Decks with views of Beach + Gulf + Pool. • Heated Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • Top floor of duplex. • Central location next to Sunset Beach.

A spacious outdoor area features a sparkling pool surrounded by lounge chairs and palm trees. A tiki hut provides shade, alongside a putting green. In the background, a rock waterslide is visible, creating an inviting atmosphere for relaxation and recreation.

5.0 out of 5 average rating, 51 reviews

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Tortuga Bay is a canalfront 5BR/3BA escape just a 2-minute walk to the beach 🏖️! Enjoy a private pool with spa & waterslide 💦, tiki hut, BBQ, new putting green ⛳, private dock for a 30ft boat ⚓, and 2 kayaks 🛶. Walk to Pine Ave dining and shops, relax in stylish coastal interiors, and experience nonstop island fun! 🌞

Popular amenities for rentals with a kayak near Bean Point Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 70 reviews

My Mistress by Beach Boutique Rentals

5.0 out of 5 average rating, 24 reviews

Home in Holmes Beach

Pergola Oasis | Walk to Beach + Outdoor Living

5.0 out of 5 average rating, 52 reviews

A vibrant blue house is surrounded by lush greenery, featuring a spacious front deck with a covered area. The yard includes a large tree and decorative stone edging, with kayaks visible nearby. The scene captures a bright and inviting outdoor atmosphere.

Home in Holmes Beach

Destination Relaxation

4.98 out of 5 average rating, 40 reviews

A screened enclosure surrounds a private swimming pool, providing a sunny outdoor space. Comfortable seating is visible alongside a dining area with a table and chairs. Lush greenery and palm trees can be seen in the background, enhancing the tropical atmosphere.

Home in Cortez

“Topside” luxury home in Cortez Village

A serene canal view is presented, showcasing calm water reflecting vibrant hues of sunset. Lush palm trees and greenery border the serene setting, complemented by a wooden dock extending into the water. The peaceful ambiance invites relaxation and enjoyment of nature.

5.0 out of 5 average rating, 66 reviews

Heavenly Hideaway, 3 bdrm, 5 minute walk to beach

Outdoor seating is provided with two teal adirondack chairs facing a serene canal. Soft lighting from string lights illuminates the wooden deck, creating a calming environment. Lush greenery in a white planter enhances the tranquil setting by the water.

4.84 out of 5 average rating, 31 reviews

Manatee Retreat A

5.0 out of 5 average rating, 23 reviews

Home in Cortez

1918 Historic Cottage • Walk/Bike to AMI Beaches

4.97 out of 5 average rating, 64 reviews

Family Fun Heated Pool, Games, Crib, Peloton

Cottage rentals with a kayak

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

4.89 out of 5 average rating, 193 reviews

4.8 out of 5 average rating, 84 reviews

Cottage in Anna Maria

Sea Whisper: North End Gem w/ Pool & Boat Dock

4.74 out of 5 average rating, 137 reviews

A well-maintained garden path is lined with pavers. A wooden fence encloses the area, with lush greenery and palm trees visible in the background. A vibrant blue gate is situated along the pathway, creating a focal point amid the natural surroundings.

Cottage in Terra Ceia

Serene Island Cottage Waterfront Haven

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida

4.88 out of 5 average rating, 16 reviews

Cottage in Holmes Beach

Waterfront Villa Delphina

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

A wooden bench is positioned on sandy ground near a serene beach. The clear blue sky is visible above, complimented by scattered clouds. The gentle waves of the ocean reflect shades of turquoise, creating a calming coastal view.

Cottage in Holmes Beach

Steps To The Beach, Private & Heated Pool, Renovat

5.0 out of 5 average rating, 6 reviews

4.96 out of 5 average rating, 80 reviews

A narrow garden path is bordered by vibrant pink bougainvillea that arches overhead, creating a colorful canopy. The ground is scattered with fallen petals, and a wooden fence is visible in the background, contributing to a serene and inviting ambiance.

Cottage in Sarasota

Cottage by the Bay - free charging, Level 2 EV

Other holiday rentals with a kayak

4.98 out of 5 average rating, 86 reviews

Townhouse in Bradenton

Nautic Star - Large pool & Free dock and kayaks

Apartment in Holmes Beach

A sign bearing the name 'Gulf Beach Place' is prominently displayed against a backdrop of palm trees. The area is surrounded by gravel and features a white fence, indicating a welcoming entrance to the condo property.

Gulf Beach Getaway-STEPS FROM BEACH

4.93 out of 5 average rating, 14 reviews

5.0 out of 5 average rating, 39 reviews

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

4.97 out of 5 average rating, 38 reviews

Heated Pool, Gym, Sauna, Cold Plunge, Hot Tub

5.0 out of 5 average rating, 46 reviews

Home in Bradenton Beach

Gorgeous 4BR w/Htd Pool | Walk 2 Beach | Boat Dock

4.93 out of 5 average rating, 28 reviews

Home in Cortez

NEW Waterfront | Heated Pool | Kayaks

A well-appointed outdoor area features an expansive heated pool with a vibrant blue hue, surrounded by stylish loungers and an outdoor dining space. Soft lighting highlights the sleek architecture of the home in the background, with lush greenery enhancing the atmosphere.

4.96 out of 5 average rating, 26 reviews

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn