Vacation rentals with a kayak in Sarasota County

Luxe Siesta Key Gem near Beach: Pool, Hot Tub, BBQ

Retreat to this luxurious 3BR 2BA getaway on the spacious waterfront property on Siesta Key, just a stone's throw away from sandy beaches, restaurants, and attractions. This stunning gem offers the perfect retreat from bustling crowds, featuring a trendy design, high-end comforts, and a majestic tropical backyard. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Backyard (Pool, Hot Tub, BBQ, Lounges, Games, Kayak) ✔ Smart TVs ✔ Wi-Fi ✔ Parking & EV Charger ✔ Bicycles See more below!

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

MCM Waterfront Retreat • Dock, Kayaks & Beaches

Welcome to our Mid-Century Modern waterfront escape on Curry Creek, minutes from Nokomis Beach (2 miles) and Venice Beach (3 miles). Spend your days fishing from the private dock, paddling one of 4 kayaks, or biking the Legacy Trail with 6 bikes. Evenings are for the firepit, grilling on the charcoal BBQ, or cornhole under the stars. We’ve stocked shark tooth gear, beach essentials, toiletries, coffee, tea, olive oil, spices, and a welcome bottle of wine — so you can arrive, unpack, and relax.

Quick and Easy Walk Downtown - Tons of Amenities

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.

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

Peaceful Oasis: King Bed & Incredible 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.

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

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 the pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.