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Vacation rentals with a kayak near Crescent Beach

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Top-rated kayak rentals near Crescent Beach

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A spacious bedroom features a large bed with a blue quilt, flanked by two bedside tables with lamps. Sliding glass doors open to a private deck, allowing natural light to flood the room. Soft blue walls complement the light-colored flooring.

Condo in Siesta Key

4.83 out of 5 average rating, 295 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

An open living area is showcased with a gray sofa, a wooden side table, and a round dining table with white chairs. Natural light filters through sheer curtains, illuminating the space. A flat-screen television and a ceiling fan contribute to the functional layout.

Bungalow in Siesta Key

5 out of 5 average rating, 9 reviews

Lagoon, pool, the Pineapple, Siesta Key Bungalows

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a queen-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

An outdoor view of the tiny home reveals a spacious yard with lush green grass. A stone pathway leads from the house to a circular fire pit area, where wooden chairs are arranged around the fire pit, offering a relaxing spot for gatherings.

Tiny home in Sarasota

4.89 out of 5 average rating, 221 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Top guest favorite

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 Sarasota

4.97 out of 5 average rating, 461 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.

An aerial view captures the serene surroundings of Vitamin Sea, nestled along the coastline. The image showcases the tranquil waters leading to the canal, with Turtle Beach nearby. Lush greenery and a small, quiet complex contrast against the vibrant blue ocean, reflecting a peaceful coastal retreat.

Condo in Sarasota

4.98 out of 5 average rating, 50 reviews

Vitamin Sea - Gulf View 2/1 with Heated Pool

Gulf View, Top Floor Condo Beautifully renovated 2BR/1BA canal-front condo just 8 min walk from Turtle Beach! Features 2 king bedrooms, full kitchen, Smart TVs, kayaks, paddleboard, heated pool & a sunset-view deck. Includes all beach gear, garage parking, BBQ lanai, and washer/dryer. Walk to restaurants or hop on the free trolley to Siesta Key Village & Sarasota. Relax, explore, and feel right at home! Feb 2026 2 week min Feb 1-14 or Feb 14-28 Mar 2026 2 week min Mar 1-16 or Mar

A serene view of the intercoastal waterway is captured, featuring calm waters reflecting the sky. Lush greenery lines the opposite shore, while a wooden dock extends into the water. Palm fronds frame the scene, emphasizing the tranquil coastal environment.

Townhouse in Sarasota

4.78 out of 5 average rating, 157 reviews

Peaceful Oasis: King Bed & Incredible Views

You have arrived, upon entering you will go upstairs to your spacious duplex. You will be greeted by an amazing view of the intercoastal waterway. You will love kayaking on the waterway & seeing all the amazing wildlife. You can sit on your downstairs patio with a cup of coffee or you can take a stroll to Turtle Beach & enjoy the sunset. Hop aboard the trolley & go to the Village & eat and drink at one of our famous restaurants or one of our favorite hot spots. See Guidebook.

An outdoor seating area is presented with dark wicker furniture, blue cushions, and an orange throw draped over the arm. A table sits in the center, with manicured grass and a view of the waterfront in the background, framed by a decorative gazebo.

4.95 out of 5 average rating, 141 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

A welcoming entrance is presented with a driveway lined by tropical foliage. A charming front porch, adorned with seating, is sheltered under a roof, inviting guests to relax. Lush greenery surrounds the property, creating a serene and private atmosphere.

Home in Sarasota

4.95 out of 5 average rating, 101 reviews

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

Top guest favorite

Cottage in Bradenton

5 out of 5 average rating, 31 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

Let your worries drift away at this unique and tranquil river house getaway we call the Lazy Gator Lodge. Craftsman cottage offering 2 large bedrooms with en suite bathrooms, open layout with great views of Braden River. The house has a large deck out back plus a fenced in yard for pet owners and families to enjoy. Centrally located for the best of Bradenton/Lakewood Ranch/Sarasota -- and its world class beaches of Siesta Key and Anna Maria.

Home in Siesta Key

5 out of 5 average rating, 4 reviews

Avanti Villa | Siesta Beach Views, Walk to Beach!

Exclusive Amenities Include: • Short Walk to Siesta Key Village & Beach • Breathtaking Views of Siesta Beach • 3 Bedroom, 3 Full Bath • Rooftop Balcony • Two Balconies With Seating Areas • Private Garage • Free WiFi • Regular & Keurig Coffee Maker, Washer & Dryer, and Kitchen Essentials Provided • Beach Essentials Provided • Gas Grill • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transp.

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

Home in Sarasota

5 out of 5 average rating, 26 reviews

Stunning Home, Heated Pool and Boat Dock

Be among the initial guests to relish in the splendor of this charming 3-bed, 2-bath abode overlooking Phillippi Creek, with a rejuvenating pool and fresh, deluxe furnishings. It offers all you need for an unforgettable escape, featuring a well-equipped open kitchen, 2 fun large Roku smart TVs in the living spaces, and a 50" Roku Smart TV in the master bedroom. Essential bathroom amenities are provided for your comfort.

A relaxing outdoor space features a sparkling swimming pool surrounded by lounge chairs with red and white stripes. Tall palm trees stand nearby, adding a tropical touch, while serene water views and lush greenery are visible in the background.

Home in Sarasota

4.91 out of 5 average rating, 58 reviews

Oceanfront Home with Heated Pool in Fishers Haven

Treat your family, friends, and beloved small dogs to an unforgettable oceanfront getaway in sunny Florida! Conveniently located near plenty of Sarasota's shopping and dining, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. The Sunshine State is waiting for you. Book today!

Popular amenities for kayak rentals near Crescent Beach

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

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

4.95 out of 5 average rating, 128 reviews

Historic Wares Creek 3 bedroom with dock access

Top guest favorite

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

4.94 out of 5 average rating, 177 reviews

Discount 33% June 3-Day and July 4-Day w/Dock-Pool

A screened-in pool area is highlighted, featuring a sparkling swimming pool with a red float. Surrounding the pool are various seating options, including lounge chairs and a dining set, all set against a backdrop of lush greenery and a spacious fenced yard.

4.89 out of 5 average rating, 185 reviews

Venice Pool Villa with Bikes Kayaks & fun!

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.

Home in Sarasota

4.92 out of 5 average rating, 95 reviews

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

A heated private pool is surrounded by a screened enclosure, providing a serene outdoor space. Lush tropical landscaping and trees create a tranquil backdrop, enhancing the sense of privacy. The pool features a gentle curve and a built-in entry handrail for ease of access.

5 out of 5 average rating, 40 reviews

Secluded 3R Pool Home Retreat Near Sarasota

Home in Sarasota

4.96 out of 5 average rating, 54 reviews

Perfect Family Getaway+ping pong, mini golf, bikes

A charming yellow house is surrounded by lush tropical foliage, featuring various palm trees and vibrant greenery. A sandy pathway leads to the front entrance, while a gravel driveway provides easy access to the property. Fencing adds privacy to the outdoor area.

Home in Sarasota

4.83 out of 5 average rating, 29 reviews

Florida Cove Cottage - 2BD/2BA in the heart of SRQ

An inviting outdoor hot tub is nestled within a screened-in area, featuring bubbles rising from the warm water. The serene environment is complemented by wooden fencing and lush greenery, creating a private space for relaxation.

Home in Sarasota

4.83 out of 5 average rating, 53 reviews

Siesta Beach Cottage. Hot Tub, Bikes, Beach Gear

Cottage rentals with a kayak

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

5 out of 5 average rating, 5 reviews

Steps To The Beach, Private & Heated Pool, Renovat

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

5 out of 5 average rating, 8 reviews

Anna Maria Cottage w/Golf Cart

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

4.96 out of 5 average rating, 77 reviews

Cottage by the Bay - free charging, Level 2 EV

Top guest favorite

The entrance of the cottage is shown, highlighted by a well-lit walkway lined with stones. The well-maintained outdoor space features small shrubs and a wooden deck adorned with a railing, leading to the inviting front door, which is flanked by vibrant accents.

Cottage in Myakka City

5 out of 5 average rating, 6 reviews

"New"Country Cottage / Lake Manatee Lakewood Ranch

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

4.9 out of 5 average rating, 165 reviews

Siesta Key Cozy Cottage across from the beach!

Top guest favorite

The exterior of a charming beach house features a light blue façade with a coral-colored door. A small table with a palm tree design is positioned on a stone pathway leading to the entrance. Lush greenery and a decorative fountain enhance the welcoming outdoor space.

Cottage in Englewood

5 out of 5 average rating, 23 reviews

The Coastal Oasis. Only 8 minutes from the Beach!

Top guest favorite

A screened-in pool area is presented, featuring a clear blue pool surrounded by stone pavers. Lush greenery and water views are visible through the screen, enhancing the sense of tranquility and connection with nature.

Cottage in Nokomis

4.99 out of 5 average rating, 82 reviews

New Pool Tropical Waterfront Dock & Optional Boat

A sandy beach stretches along the calm waters, showcasing gentle waves under a partly cloudy sky. Lush greenery lines the shoreline, and a wooden staircase leads to the beach, providing access to the serene outdoor environment.

Cottage in Englewood

5 out of 5 average rating, 28 reviews

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

Other great vacation rentals near Crescent Beach

Top guest favorite

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

Condo in Siesta Key

4.92 out of 5 average rating, 103 reviews

Beautiful White Sand Siesta Key Beach

Condo in Siesta Key

4.92 out of 5 average rating, 126 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

Top guest favorite

A full bathroom features a large shower with a modern design. Glass doors offer a clear view of the light-colored stone flooring and the elegant tile wall, which has a contrast of dark and light tiles. A compact vanity and toilet are also visible in the background.

Apartment in Sarasota

5 out of 5 average rating, 190 reviews

Modern Luxury Apartment in a House Near Siesta

A sign indicating 'Siesta #1 Beach in the USA' is framed by tropical greenery and sandy pathways. The beach stretches in the background, with colorful umbrellas dotting the shoreline under a clear blue sky.

Condo in Siesta Key

4.9 out of 5 average rating, 119 reviews

Crystal House on Siesta Key Beach

Top guest favorite

Home in Sarasota

5 out of 5 average rating, 335 reviews

Stunning Luxe Casita- Gateway to Siesta Beach

An aerial view showcases the coastline of Siesta Key, featuring white sandy beaches meeting vibrant turquoise waters. The gentle curve of the shoreline is lined with residential buildings and lush greenery, with the town and city skyline in the distance under soft morning light.

Apartment in Sarasota

4.86 out of 5 average rating, 119 reviews

Luxury King Suite

Condo in Sarasota

4.91 out of 5 average rating, 218 reviews

Near beach. Daily rentals. Pool. king bed

A serene view is presented, featuring soft, white sandy beach leading to clear, turquoise waters. The horizon showcases a blend of clouds and blue sky, creating a tranquil coastal environment. Gentle waves are seen lapping at the shore, inviting relaxation.

Guesthouse in Sarasota

4.91 out of 5 average rating, 111 reviews

Super Clean Cozy and Quaint steps from the beach

Quick stats about vacation rentals with a kayak near Crescent Beach

Total rentals
20 properties
Nightly prices starting at
€ 209 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore