Holiday rentals with a kayak in Sarasota Beach

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

We cover your Airbnb service fees! Enjoy an updated and welcoming coastal getaway on the island of Siesta Key at the charming Solitude Suites. The “Sunset Suite” features a cozy living/dining/kitchenette area with a 65” TV, plus a separate bedroom and bathroom. Step out from the bedroom onto your private open wood deck, complete with table and chairs for taking in breathtaking Siesta Key sunsets. A brand-new shower was added in December 2023! Just a 2-minute drive or 10-minute walk to the bea

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!

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

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!

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

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!

@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)

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

The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.

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.

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.

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

Chic Properties Presents: Par in Paradise ⛳️ A modern 3 bedroom + private studio suite(counted as 4th bedroom), 3 bathroom Sarasota retreat that comfortably sleeps 10. Inside, enjoy open living, and a fully equipped kitchen. The resort-style backyard is the true highlight, featuring a sparkling heated pool, hot tub, fire pit, and putting green. Just minutes from beaches, dining, and golf, this retreat is a true hole-in-one.

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