Holiday rentals with a kayak near Crescent 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

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

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. This is a resort that has something for everyone. The Catamaran Bungalow features a bright and airy one bedroom space; with a large 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. The living room has a sofa that turns into a queen size bed, allowing for a max occupancy of three.

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

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.

@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)

Gertrude's Siesta | Bayview Pool Tennis Beach!

The Starfish at Bay Oaks Tranquil bayside Siesta Key unit with heated pool, water-view private patio, and tennis or pickle court. Additional free amenities include fishing dock and day-boat slip, bayside grilling and lounging, beach gear, and club house with billiard room. Walk just 1-minute to bay-front and pool, 15-minutes to world famous Siesta Beach access 12, or just 2-minutes to Free Trolley serving all Siesta Key beaches and dining. Book a getaway today!

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.

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

2 BR Waterfront Condo on Siesta Key | Turtle Beach

Welcome to Day Dreaming! This 2 bedroom 1 bath rental offers everything you could dream of and more. Located just 300 yards from Turtle Beach, this oasis offers a beautiful communal pool and private dock for you to fish off of. Restaurants and bars are just a short walk away and the free trolley is able to pick you up at turtle beach and take you anywhere your heart desires on the key.

Island escape w/ pool, bikes & beach essentials

Welcome to your easygoing Siesta Key escape - steps from the beach, the Village & a heated pool. - Sleeps 10 | 3 bedrooms | 5 beds | 2 baths - 2-min walk to Siesta Key Beach, 4-min to the Village - Shared heated pool - open 24hrs, all year - Full kitchen, washer/dryer & free WiFi - Bikes, kayak & beach essentials included - Pet-friendly (fee applies)