Vacation rentals with a kayak in Sarasota County

4.91 out of 5 average rating, 111 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

4.97 out of 5 average rating, 69 reviews

A spacious bedroom features a large bed with a light blue and white bedding arrangement. A ceiling fan circulates overhead, and natural light flows in from sliding glass doors leading to an outdoor area. A large indoor plant adds a touch of greenery.

Home in Sarasota

Winter Haven Retreat – Steps to Bay & Ringling

Tropical Paradise by the Bay – Walk to Ringling Museum, Asolo Theatre! Nestled between two university campuses and just a 5-minute walk to Sarasota Bay, 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!

4.96 out of 5 average rating, 402 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)

4.97 out of 5 average rating, 505 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.

Guesthouse 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.

5 out of 5 average rating, 4 reviews

Home in Sarasota

Colorful Sarasota Home

Whimsical Artsy Sarasota Vibe. Clean, private and tons of outdoor living area. This 2 Bed 2 Bath home is the perfect spot to stay if you want close to all the shops and restaurants downtown and quick access to St Armands circle, Lido beach, Longboat Key and Siesta Key. WIFI and Smart TV's in living and both bedrooms. Fully equipped kitchen and brand new washer and dryer in the laundry room off the kitchen. Come enjoy wonderful Sarasota and her Islands, Parks and Golf courses. 0091983

5 out of 5 average rating, 100 reviews

A spacious home is set on a well-maintained lawn, featuring a white exterior complemented by lush tropical landscaping. Palm trees and shrubs enhance the entrance, while a smooth driveway leads to a two-car garage. The sky is clear and blue, adding to the inviting appearance.

Home in Port Charlotte

Elegant heated pool canal home in very quiet area.

Great location! Bring your dog, bring your boat and enjoy the Florida sun in your heated saltwater swimming pool. Fish off your private dock while watching for dolphins or manatee. You can meet the rest of the opacarophiles who walk to the beach to view the sunset. Relax in the jacuzzi with your favorite beverage. NOTE: Beach is sandy but the water is BRACKISH, not clear. This is mostly a retirement neighborhood. This is NOT a party house and not suitable for unattended children.

4.78 out of 5 average rating, 176 reviews

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

Relaxing Retreat, King Bed, Beautiful Scenic 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.

4.94 out of 5 average rating, 32 reviews

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

Home in Port Charlotte

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

4.88 out of 5 average rating, 127 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.

4.88 out of 5 average rating, 151 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 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.

5 out of 5 average rating, 102 reviews

Condo in Sarasota

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

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.