Holiday rentals with a kayak near Crescent Beach

5.0 out of 5 average rating, 109 reviews

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

Super rare 2 week opening just popped up Feb 2027! Whisk your favorite person away to BayDreaming! Retreat to this quiet 1BR/1.5BA condo,just an 8‑minute walk from Turtle Beach. Perfect for couples, it offers a private deck with canal and Gulf views, a heated pool for sunset swims, two supyaks, and a plush king bed for cozy nights.Enjoy garage parking, beach gear, and a peaceful community.Whether you’re here to relax or reconnect, this coastal retreat blends romance with Siesta Key serenity.

4.91 out of 5 average rating, 207 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!

Adorable totally renovated !!!Siesta key cottage one block from the beautiful white sand beach and two blocks from the iconic Siesta Key Village on the north end of the island. Everything is a short walk including all the shops and restaurants of Siesta Village. Very private fenced in yard with plenty of comfy furniture and barbecue:) Very nice size stainless steel/granite kitchen with a dining room and a large sunken living room. Both the living room and the bedroom open to the private patio!

4.92 out of 5 average rating, 124 reviews

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

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

A living area is presented with light tile flooring and a comfortable blue armchair. A wall-mounted TV displays a beach scene. A wooden sideboard adds character, while a dining space with white-painted chairs and a chandelier is visible in the background.

4.91 out of 5 average rating, 89 reviews

Sun and Sea Gem on Siesta Key

Sun and Sea Gem on Siesta Key is your perfect spot to unwind in style and comfort! Ideally located just across the street from the beach and one of the best spots on the island. Relax and enjoy smart TVs and a fully equipped kitchen that makes dining in a breeze. Just a short stroll away from local favorites like Captain Curt’s, Lenny’z Pizza, Jakes ice crème, shops, bike and kayak rentals and more. Relax by the heated pool or take a peaceful walk on the beach to catch breathtaking sunsets.

5.0 out of 5 average rating, 11 reviews

Home in Sarasota

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

Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

4.95 out of 5 average rating, 421 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 + wildlife viewing)

4.98 out of 5 average rating, 52 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

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 king-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 queen sofa-bed allows accommodations for three guests.

4.87 out of 5 average rating, 312 reviews

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

Apartment in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Huts. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

4.95 out of 5 average rating, 19 reviews

Apartment in Siesta Key

Gertrude's Siesta | Palm-view Pools Private-Beach!

Palm View Unit Bayside unit with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta!

4.88 out of 5 average rating, 139 reviews

Condo 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.

4.94 out of 5 average rating, 18 reviews

Island home w/ pool, kayak & BBQ

Welcome to your Siesta Key escape - a bright, walkable island home just steps from world-famous white sand & the Village. - Sleeps 10 | 3 bedrooms | 5 beds | 2 baths - 2-min walk to Siesta Key Beach, 4-min walk to Village - Shared heated pool (open 24hrs, year-round) & outdoor dining - Bikes, kayak, beach essentials & BBQ included - Free WiFi, 4 HDTVs, fully equipped kitchen & free parking (2 cars) - Pet-friendly (fee applies)

4.95 out of 5 average rating, 110 reviews

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

New Pool Tropical Waterfront Dock & Optional Boat

Located on a highly desirable street, the house is perched high above Curry Creek offering spectacular water views from every room. The property includes a boat ramp to avoid the public launch. Three kayaks (two tandems and one single). Two miles from Nokomis Beach and only half a mile from The Legacy Bike Trail. You can do so many fun things, or just have a drink on the dock and watch the manatees. Pet Friendly

Popular amenities for kayak rentals near Crescent Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a Kayak

5.0 out of 5 average rating, 125 reviews

River House with Kayaks. Relax on the River.

5.0 out of 5 average rating, 113 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

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, 122 reviews

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

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.

4.96 out of 5 average rating, 149 reviews

Historic Wares Creek 3 bedroom with dock access

4.81 out of 5 average rating, 117 reviews

Home in Bradenton Beach

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

4.95 out of 5 average rating, 207 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

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

A private heated pool and spa are surrounded by natural stone tiles, with lounge chairs and a dining set nearby. Tropical palm trees provide shade, and a colorful inflatable pool toy is visible in the water. The serene backdrop features the intercoastal canal.

5.0 out of 5 average rating, 23 reviews

Stroll to the Sea, Steps to the Village, Boat dock

4.97 out of 5 average rating, 64 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

Cottages with a kayak

4.97 out of 5 average rating, 39 reviews

Cottage in Lido Key

Lido Key Beach Bungalow with Private Heated Pool!

4.97 out of 5 average rating, 71 reviews

Cottage in Bradenton

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

4.8 out of 5 average rating, 83 reviews

Cottage in Anna Maria

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

4.87 out of 5 average rating, 15 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

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

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

Other holiday rentals with a kayak

5.0 out of 5 average rating, 32 reviews

Guest suite in Sarasota

siesta breeze paradise suite

4.91 out of 5 average rating, 43 reviews

A living area features a comfortable sofa arranged around a round coffee table. A wall-mounted television displays a sunset over water. Natural light fills the space from windows, complemented by a ceiling fan and neutral-toned walls, creating a fresh and open atmosphere.

Condo in Siesta Key

2 BR Waterfront Condo on Siesta Key | Turtle Beach

An aerial view showcases the waterfront property, highlighting the building's proximity to the canal. Nearby greenery and water feature prominently, while the surrounding area includes various residential and commercial structures, indicating a vibrant community. The pool is visible, situated on the property.

4.94 out of 5 average rating, 34 reviews

Waterfront w/ Pool, mins to SK Beaches, bikes/sups

4.95 out of 5 average rating, 22 reviews

Siesta Key Direct Beachfront incl kayaks & SUPs

An inviting outdoor space features a clean, turquoise pool surrounded by elegant stone paving. Lounge chairs are positioned nearby for relaxation. Large screens enclose the area, offering a sense of privacy while allowing sunlight to filter through. A grill is visible in the background.

4.86 out of 5 average rating, 7 reviews

Villa Champagne | Pool, Spa, Dock, Walk to Beach

4.95 out of 5 average rating, 38 reviews

Siesta Key Oasis Walk to Beach, Pool, Hot Tub, BBQ

5.0 out of 5 average rating, 88 reviews

Guest suite in Sarasota

siesta breeze suite

A bright, newly updated coastal home stands proudly with a paved driveway, flanked by palm trees. The exterior features a classic stucco finish with terracotta roof tiles, and the garage doors are designed with a modern aesthetic. An electric golf cart is parked in front.