Holiday rentals with a kayak in Sarasota County

4.97 out of 5 average rating, 60 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

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

Superhost

5 out of 5 average rating, 5 reviews

Coconut Cottage | Walk to Lido Beach & St. Armands

🦩 Exclusive Amenities Include • Private Heated Pool & Spa • Outdoor Lounge Area with TV, Exterior Heaters, Fire Table , Dinning Area, & Ping Pong Table • Less than a 2 minute walk to St. Armands Circle • Less than a 6 minute walk to Lido Key Beach • 4 Bedrooms, 3 1/2 Bathrooms • 2 King Beds, 2 Queen Beds, & 1 Twin Roll Away Bed (Sleeps 9) • Water Filtration System Added • Free WiFi & 4 Smart HDTV’s with Cable • Beach Towels, Chairs, Cooler, & Caddy Provided • 4 Bikes & 2 Kayaks with Life Vests

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.

4.91 out of 5 average rating, 115 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

4.86 out of 5 average rating, 139 reviews

Home in Longboat Key

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Superhost

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

4.88 out of 5 average rating, 156 reviews

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.

4.95 out of 5 average rating, 410 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, 516 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.

4.81 out of 5 average rating, 16 reviews

Water Access Retreat | Kayaks + Hot Tub

BNB Breeze Presents: Water Access Retreat! Nestled in the heart of Sarasota, Florida, Water Access Retreat is a delightful property that offers a serene escape with direct access to a nearby kayak ramp, making it the perfect base for exploring the stunning waters of Sarasota Bay. Step outside and soak up the Florida sun or unwind after a day of adventure. - Hot Tub - Two kayaks and direct access to nearby kayak ramp - Private yard and patio with outdoor seating - Smart TV - and More!

5 out of 5 average rating, 103 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.

5 out of 5 average rating, 6 reviews

Luxury Waterfront Home in Sarasota w/ Pool & Dock

Exclusive Amenities Include: • Private Heated Saltwater infinity-edge Pool & Spa • Canal front with Breathtaking Intracoastal Views • 4 Bedrooms - 2 Primaries with Ensuite Bathrooms for a total of 3 Full Baths • Outdoor Lounge Area - Private Heated Pool with Baja Shelf, Gas Grill & Outdoor Kitchen • Private Boat Dock • Dock Fishing • Free WiFi & HD Smart TV’s • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Cart

4.98 out of 5 average rating, 131 reviews

An open-concept kitchen features a large granite island with seating, surrounded by white cabinetry and modern appliances. Natural light floods the space, highlighting the stylish chandelier above. The dining area is visible in the background, along with inviting seating arrangements in the family room.

Villa in Englewood

Stunning Bay Waterfront!

Spectacular Lemon Bay views! Upstairs at Blue Island Inn, waterfront “Bella Vista” with Bay & Pool views! 2 bedrooms; kitchen & 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)