Holiday rentals with a kayak in Sarasota

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.

LocationValueIndoor spaces

4.83 out of 5 average rating, 307 reviews

A bright blue entrance door labeled 'Poolside Suite' is visible, leading into the suite. The door is framed by a light blue exterior, with a view of the pool area and palm trees in the background. Sunlight casts gentle shadows on the patio.

Flat in Siesta Key

Siesta Key - Poolside Suite - Studio - Heated Pool

The Poolside Suite offers a comfortable hotel-style stay with a king-sized bed and a 65” smart TV, plus free Wi-Fi. The private en suite bathroom includes a walk-in shower, toilet, and a spacious vanity with sink and mirror. Between the walk-in closet and pantry you’ll find a fridge, microwave, freezer, cups, plates, silverware, Keurig, iron, mini ironing board, and hangers. Simple yet stylish, it has all the essentials without any frills. The centralized A/C is set between 71–73 degrees, with

ValueLocationLaundry

4.98 out of 5 average rating, 83 reviews

Winter Haven Retreat – Steps to Bay & Ringling

Tropical Paradise by Sarasota Bay – Walk to Ringling Museum, Asolo Theatre! Just a two minute walk to New College and its beautiful bayfront promenade, this 2,200 sq ft tropical retreat beacons you to unwind. Enjoy 3 very private bedrooms, an office area, spacious living room, and a huge fenced-in backyard perfect for kids and pets—all less than 15 minutes from Lido Beach and café-lined St. Armands Circle. Kayaks, hammock, grill, foosball, sandbox, basketball hoop, and more await your stay!

Outdoor spacesLocationHospitality

4.96 out of 5 average rating, 123 reviews

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.

Home in Bradenton

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

Outdoor spacesValueBathroom

A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.

4.92 out of 5 average rating, 124 reviews

Heated Pool - Just 1 mile to Beach! Updated/Fun!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

Outdoor spacesValueHiking

4.83 out of 5 average rating, 123 reviews

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

LocationOutdoor spacesHot tub

4.88 out of 5 average rating, 159 reviews

The cabin's interior features warm wooden walls and ceilings. A spacious bed is positioned in the main area, while a small loft above is accessed by a ladder. Natural light fills the room through multiple windows, highlighting rustic decor including a painting and a green lamp.

Farm stay in Myakka City

Florida Cracker Cabin on cattle ranch/Myakka River

We are located in Myakka City, FL, which is a short drive to Siesta Key and Lido Beach and Sarasota! Enjoy a peaceful stay in our newly built, unique, air-conditioned cracker cabin. The cabin sleeps 4 guests (2 adults comfortably and 2 children) and is located in the middle of our 1,100 acre working cattle ranch. Step outside and you are right on the Myakka River and can sit by the fire-pit at night and enjoy the sounds of nature. While your visiting, enjoy a kayak down the Myakka River.

Outdoor spacesValueBiking

4.97 out of 5 average rating, 528 reviews

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.

Guest house in Sarasota

Coolest Downtown Neighborhood - Ebikes, Beach Gear

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.

ValueLocationCondition

4.95 out of 5 average rating, 425 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking

LocationValueParking

4.99 out of 5 average rating, 144 reviews

An enclosed lanai features multiple large windows with views of Lemon Bay, allowing natural light to fill the space. A palm tree is visible outside, framed by the window panes. A decorative area rug is positioned on the wooden floor, enhancing the coastal ambiance.

Villa in Englewood

Stunning Bay Waterfront! Jaw dropping Water Views!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchenette & family room. Enjoy “Lemon Bay-front beach” in backyard. Low-key quiet vacationers. 1 car parking spot. No visitor parking. Free 2 kayaks. Login to your favorite streaming services with Smart TVs. Beautiful Blind Pass Beach, Englewood Beach, 5 restaurants & Tiki Bars are just 1.5 mile away or hop on Stumpy's Free Shuttle (tip based)

ValueOutdoor spacesLaundry

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.

LocationOutdoor spacesAccuracy

4.88 out of 5 average rating, 139 reviews

5.0 out of 5 average rating, 109 reviews

Apartment in Sarasota

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

💙 Rare 2-week opening for February 2027! Escape the winter together at BayDreaming, a romantic 1BR/1.5BA retreat just an 8-minute walk from Turtle Beach. Sip sunset cocktails on your private canal- and Gulf-view deck, enjoy a heated pool, paddle the included SUPYAKs, and unwind in a plush king bed. With garage parking, beach gear, and peaceful waterfront surroundings, it’s the perfect Siesta Key escape to relax, reconnect, and soak up the sunshine.

Outdoor spacesLocationWifi

Popular amenities for kayak rentals in Sarasota

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 107 reviews

A canalfront area features a serene gazebo surrounded by lush green grass and white pebbles. The vibrant sunset sky adds warmth to the scene, and the private boat dock is visible in the background, enhancing the tranquil outdoor setting.

Home in Port Charlotte

Xanadu|Fishing/ Pool/Dock|Kayaks|Bar/Gazebo/ Kids

Outdoor spacesLocationParks

4.96 out of 5 average rating, 150 reviews

A wooden dock extends over calm waters, surrounded by palm trees. A covered seating area with a table and several lounge chairs is present, offering a relaxed spot for enjoying nature. Nearby houses are visible across the water, contributing to the serene environment.

Home in Bradenton

Historic Wares Creek 3 bedroom with dock access

LocationOutdoor spacesRiver

4.95 out of 5 average rating, 210 reviews

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.

Home in Anna Maria

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

Outdoor spacesLocationPool

5.0 out of 5 average rating, 125 reviews

Home in Bradenton

River House with Kayaks. Relax on the River.

LocationValueRiver

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

ValueOutdoor spacesCleanliness

4.97 out of 5 average rating, 66 reviews

A spacious living area features a light-colored sectional sofa and a round coffee table in the center. Natural light pours in through large windows, illuminating the room's wood accents and open layout. A dining area with a wooden table and chairs is visible in the background.

Home in Osprey

Charming Florida Cottage - Kayaks Included

Outdoor spacesLocationNearby

5.0 out of 5 average rating, 23 reviews

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

Outdoor spacesLocationPool

5.0 out of 5 average rating, 12 reviews

Luxury 3B/3B waterfront home w/ pool + boat access

LocationOutdoor spacesComfort

Cottage rentals with a kayak

4.91 out of 5 average rating, 208 reviews

A sunken living room is seen, featuring a gray sectional sofa and a blue sofa. A coffee table sits between them, complemented by a unique side table. A television is positioned on a stand opposite the sofas, with light streaming through the window-covered double doors.

Cottage in Siesta Key

Siesta Key Cozy Cottage across from the beach!

ValueLocationIndoor spaces

4.9 out of 5 average rating, 211 reviews

Two individuals ride bicycles along a sandy beach at sunset, with vibrant hues of orange and purple in the sky. Gentle waves lap at the shore, and distant figures can be seen walking along the coastline, creating a serene beach atmosphere.

Cottage in Englewood

Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath

ValueOutdoor spacesBeach

4.9 out of 5 average rating, 152 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

LocationOutdoor spacesView

Cottage in Pass-a-Grille Beach

Steps2Beach-Walk everywhere-Bikes & gear Included

ValueLocationQuiet

4.89 out of 5 average rating, 193 reviews

4.97 out of 5 average rating, 73 reviews

Cottage in Bradenton

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

Outdoor spacesLocationAmenities

5.0 out of 5 average rating, 38 reviews

Cottage in Englewood

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

LocationOutdoor spacesKitchen

Cottage in Don Pedro Island

Island Getaway, Beach House, Dock, Pet Friendly

ValueLocationAir conditioning

4.99 out of 5 average rating, 79 reviews

4.93 out of 5 average rating, 29 reviews

A cozy deck is featured with two chairs and a hammock, overlooking the peaceful landscape. Strings of lights enhance the space, while the sky transitions from blue to dusk. Nearby, views of open fields can be seen, creating a tranquil outdoor retreat.

Cottage in Myakka City

New Country Cottage on Lake Manatee Lakewood Ranch

Outdoor spacesLocationHospitality

Cabin rentals with a kayak

4.97 out of 5 average rating, 66 reviews

The bedroom features a spacious bed with a blue coverlet complemented by a seating area with light blue cushions. A ceiling fan provides air circulation, and natural light enters through a window with blinds. Two framed pictures adorn the wall near the bed.

Cabin in Arcadia

Riverfront Cabin W/ Kayaks

LocationOutdoor spacesAccuracy

4.98 out of 5 average rating, 45 reviews

The interior features a collection of motorcycle memorabilia displayed on the walls, alongside vintage drag racing images. Two motorcycles are showcased on a smooth floor, with a colorful carpet beneath. A staircase lined with motorcycle wheels leads to a loft space, enhancing the room's unique style.

Cabin in Englewood East

Unique loft experience for motorcycle enthusiasts

LocationHospitalityComfort

Waterfront Retreat- w/Kayaks & Peace River access

LocationOutdoor spacesBathroom

5.0 out of 5 average rating, 69 reviews