Vacation rentals with a kayak in Siesta Key

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Top-rated accommodations with a kayak in Siesta Key

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with 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, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Guest favourite

Condo in Nokomis

5 out of 5 average rating, 35 reviews

Family Friendly Beach Condo

Property located on Lyon’s Bay, in Nokomis, Florida. This three-bedroom upper Condo unit is situated within a ten minute walk to Nokomis Beach on the Gulf of Mexico. Open kitchen fully equipped, Office area. Wi-Fi Large master suite, second bedroom has a queen bed. Third bedroom features four twin beds, walk-in closet and its own full bath. Your stay comes with access to paddle boards kayaks, which can be launched from a floating dock. Also available for your use are beach chairs and coolers.

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 502 reviews

Studio Apartment. Priv Yard. 5 min to Siesta Key!

Self checkin. Includes kayak and bikes! You’ll love my place because of the coziness, the high ceilings, and the location. My place is good for couples, solo adventurers, and business travelers. Converted garage space. Your own private fenced back yard, kitchenette, fridge, private bathroom, Amazon Firestick with Netflix, Hulu and dock/boat ramp just 30 sec from your door and in a beautiful neighborhood. Just a 10 min bike ride to Siesta Key. The #1 beach in America! What more could you ask for!

Superhost

Bungalow in Siesta Key

4.89 out of 5 average rating, 9 reviews

Lagoon, pool, the Catamaran at Siesta Key Bungalow

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and a private bathroom you'll feel at home. The Catamaran Bungalow is stocked with linens, care essentials, plus eating & cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

Guest favourite

Rental unit in St. Petersburg

4.93 out of 5 average rating, 55 reviews

Centrally Located Coastal Retreat- kayaks included

This charming two-bedroom, one-bath retreat offers a comfortable stay for up to 6 people, with the flexibility to accommodate an additional guest. Situated in a quiet and family-friendly neighborhood, you'll appreciate the tranquil atmosphere during your stay. The location is convenient, with downtown St. Petersburg just a short 10-minute drive away. Additionally, you'll find yourself within a 10-minute drive of beautiful local beaches such as Madeira Beach, Saint Pete Beach, and John's Pass.

Guest favourite

Home in Sarasota

5 out of 5 average rating, 13 reviews

Beautiful MidCentury Modern Home

Our charming 2BR/2Bath mid-century modern home just steps from the water. Explore Sarasota's beautiful mangroves and beaches with our kayak or bicycle to nearby attractions. Enjoy the open floor plan, modern kitchen, and comfortable living room with sectional couch and TV. The primary bedroom offers a queen bed and office space. The second bedroom has a full bed and TV. Recently remodeled bathrooms and a separate laundry room add convenience. Siesta Key Beach is only six miles away. No pets.

Guest favourite

Home in Ruskin

4.95 out of 5 average rating, 168 reviews

Private Beach Nature 2 ppl pets Work space remote

Unique, modern beachfront guest house-sits on a MULTI million $ property. Blend of Frank Lloyd Wright & Luis Barragan design. Located on Tampa Bay btwn Sarasota and Tampa/St Pete. Surrounded by palm trees, mangroves, birds chirping, dolphins, manatees, waves gently lapping and breezes. Sand from door to private beach. Fresh sheets, outdoor shower, small fridge, microwave, air fryer, & in and outdoor seating areas. Kayak and paddle board available. SUNRISE'S UNIQUE We are DOG FRIENDLY!

Superhost

Townhouse in Sarasota

4.77 out of 5 average rating, 131 reviews

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.

Superhost

Townhouse in Ruskin

4.93 out of 5 average rating, 212 reviews

Waterfront Townhome w/ Heated Pool & Balconies

Relaxation awaits you the moment you step in to Bahia Bungalow, a 2 Bedroom, 1.5 Bath town home nestled in Little Harbor Resort. Little Harbor is located on a partially private guest reserved beach in Ruskin, a short drive from Tampa, Sarasota & St. Pete. The resort overlooks Tampa Bay & features a heated outdoor pool, basketball and pickleball courts, fitness area, a playground & a marina. Dining within the Resort include a bay-view restaurant, a poolside bar/grill.

Guest favourite

Rental unit in St. Petersburg

4.9 out of 5 average rating, 135 reviews

Walk score 82 | bikes | kayak | 214mbps | foam bed

♡ 400ft²/38m² private craftsman studio apartment on shared property ♡ ☞ Walk Score 82 (walk to cafes, dining, shopping..) ☞ Bike Score 75 (2 bikes provided) ☞ Memory foam mattress + sofa couch ☞ Fully equipped + stocked kitchen (K-cup) ☞ Free kayaks + beach gear ☞ Onsite parking ☞ Smart TV w/ Netflix ☞ 214Mbps Wi-Fi ☞ AC & Heat 5 min → Salvador Dall Museum, Vinoy Park, St. Pete Pier 15 min → Airport & St Pete Beach ***Send me a message for current promos***

Guest favourite

Condo in Sarasota

4.98 out of 5 average rating, 40 reviews

Canal Front Oasis-2 BR Peaceful-Htd Pool-Kayak/Sup

Escape to Paradise: Top-Floor Beach Condo with Gulf Views Welcome to our stunning 2-bedroom, 1-bath top-floor condo, where modern comfort meets beachy charm. Nestled along a serene canal with breathtaking Gulf views, this recently remodeled retreat is the perfect backdrop for an unforgettable vacation. Top floor! Tandem Kayak and one paddleboard included! Heated pool! Small, quiet complex! Less than 1/2 mile to Turtle Beach and the free trolley!

Superhost

Home in St. Petersburg

4.83 out of 5 average rating, 212 reviews

Bungalow near the sea

Welcome to our bungalow by the sea It is just 3 blocks away from waterfront Lassing Park, which can be enjoyed with kayaks and bicycles that are available for free, and perfect for exploring nearby downtown Saint Petersburg and the pier. The house is completely furnished with everything you need for a great stay. Charcoal grill, TV, coffee, Ironing board and iron , Wi-Fi Internet and Beach toys So kick back and relax and enjoy your stay.