Holiday rentals with a kayak near Crescent Beach

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.

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 Coquina Bungalow features a bright & airy one bedroom space; with a living room & full-kitchen. With a king-size bed, private patio & private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating & cooking utensils. The living room has a sofa that turns into a queen size bed, allowing for a max occupancy of three.

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

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!

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!

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

@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)

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!

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

Beach, Village, Dock & Private Pool! One-of-a-kind

Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

4B w/ Heated Pool | Walk to Siesta Key Beach!

Beach days, pool nights, and waterfront adventures—all in one unforgettable Siesta Key getaway. Just an 8–10 minute walk to the beach, this canal-front retreat features a private heated pool, dock, kayaks, and paddleboards. End the day in the sunroom, challenge friends on the cocktail arcade, or explore Siesta Key Village just minutes away 🌴🌿