Townhome holiday rentals in Siesta Key

Downtown Living, Steps to Parks, Newly Furnished

Experience Sarasota like a local at Sarasota Sunrise, a freshly furnished two-bedroom retreat designed for both relaxation and convenience. Start your mornings with coffee in the cozy living room or take a short stroll to Gillespie Park for tennis, basketball, or a peaceful walk under the trees. After a day exploring downtown’s cafés, shops, and cultural spots, return to your private space with a fully equipped kitchen, comfy queen bedrooms, and all the modern comforts you need. Whether you’re h

Getaway Family Beach Townhome w/Pool!

Wouldn't you like to get away?🌞 Just steps to the perfect family beach at this condo w/pool. Two bedrooms, two baths (+tub), sleeps six! King bed, queen w/twin bunk over, one convertible queen. Fresh updates: Washer-dryer, flooring, sofa, full kitchen, cable, wifi, beach toys, pack n play, baby gate. Did we mention the heated pool?🏊‍♀️ Next door to Walgreens, restaurants, bike rentals, shops, grocery. So many charming delights to discover on America's best beach, Anna Maria Island (AMI)!🏖

Private Beach Access - Spacious & Modern Gem!

Stay, relax, and play-your Siesta Key retreat is here. Make lasting memories at this cozy Siesta Key townhouse, just steps from the famous white sands. Private beach access and no roads to cross, it’s safe and stress-free for the whole family. Relax in spacious living areas, cook in the full kitchen, or enjoy games and movie nights after a day in the sun. Highlights include 2 bedrooms, private parking, nearby shops and dining, and the free Siesta Key Breeze Trolley for easy island exploring.

Sunny Retreat at Sienna Park: Family Gateway

Discover your family getaway at this stylish 2-bedroom, 2-bath condo in the heart of Sarasota. Perfectly located just minutes from beautiful beaches, shopping, and dining, this modern home offers a serene atmosphere for relaxation. Enjoy a fully equipped kitchen, cozy living space, and all the essential amenities for a comfortable stay. Ideal for families seeking both tranquility and convenience, your oasis at Sienna Park awaits. Book now and create unforgettable memories in sunny Sarasota!

Heated Pool•Lake view•Beach Stuff•Baby Gear•3 beds

Welcome! Only 25 min. to Anna Maria Island and Lido Beach, 35 min. to Siesta Key and 17 min. to IMG Academy. Located in the gated area between Sarasota and Bradenton, close to Sarasota Airport. Relax in the heated pool, play pickleball and basketball, and visit the shops and restaurants just a 5-minute walk away. • 2 queen and 1 king size beds • Each bedroom has smart TV and bathroom • Stunning lake view from screened lanai Start your perfect vacation today! Absolutely no smoking!

Relaxing Retreat, King Bed, Beautiful Scenic 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.

Bright & Modern - Sarasota Home

Centrally located in Sarasota, Florida—an inviting home that blends modern style with a quiet setting. This sunny retreat is filled with natural light, making it feel bright and welcoming. Unmatched amenities, including a well-equipped kitchen, roomy living spaces, along with a community pool. Beyond its comfy indoors, you can easily get to Sarasota's beautiful beaches, cultural spots, and great restaurants making this Sarasota spot a perfect mix of quiet and convenience.

100 Steps to beach access & 5-min Village walk

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

Siesta Key Getaway with King Bed

Great vacation location on beautiful Siesta Key, fully updated unit, (no busy street to cross) with private & gated direct beach access. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Come join us for the perfect vacation.

Cast a Waves W/heated pool

Enjoy Siesta Key with luxury! This beautiful Townhouse is located just 3 blocks from Siesta Key Village (with shops and restaurants) and only 1 block from the beach! This great home greets you with solid surface floors and a beautiful chefs kitchen! With sleeping up to 9 guests you will be able to bring your whole family with plenty of room and beds! Once you have enjoyed to beach for the day you can relax by the private pool out back located on a canal!

Green Jacaranda AMI Duplex A, 5 min walk to beach

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available.MAX Occupancy - 4 people including children of any age.