Townhome holiday rentals in Siesta Key

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Midnight Cove II 220D - Peaceful Bayside Vacation!

Midnight Cove II Unit 220D is ready for your upcoming getaway! This stunning three-bedroom condo offers the perfect blend of relaxation and adventure, located in the heart of Siesta Key, where the local community thrives with exceptional shopping, dining, art, and culture. Enjoy the convenience of the FREE Siesta Key Breeze Trolley, making your exploration effortless without the hassle of parking. Plus, with dedicated beach access just a short stroll away, you’ll be able to dig your toes in the

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)!🏖

Siesta Key - Private Beach Access - 2BR Retreat

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.

Steps from Beach! Heated Pool & Spacious Lanai!

Welcome to Your Dream Beach Escape! One block from the sugar-white sands of Holmes Beach, this freshly renovated coastal gem is ready to host the vacation you have always dreamed of! Cruise the island on provided bikes, use our paddle boards to float among the waves, and hit the beach with all the gear provided. Don't forget to enjoy the shared, HEATED pool! At night explore the laid-back magic of Anna Maria Island—shops, eats, and island vibes just a short bike ride away from our home.

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!

Gulf and Beach Views-Steps from Beach and Village

My townhome is just steps to Siesta Key Public Beach and Siesta Key Village, nightlife and great restaurants. You’ll love this location because of beach views from the master bedroom, short walk to the beach and short walk to the village. My place is good for couples and families (with kids). It has a beautiful shared pool and gives you the luxury of beautiful accommodations with the laidback feel of Siesta Key. Beach chairs, towels, toys and a beach cart are available for use too!

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.

Villa Marina (1 Block from beach with heated pool)

This centrally located Siesta Key condo rental is just steps from Siesta Key Village and beautiful Siesta Key Beach! Enjoy time with the family by the heated community pool or catch some sun at the beach just 1 block away. This 2 bedroom 2 bath condo is a great space for you with a king bed in the master room an en-suite bath and two twin beds in the second room with separate bath across the hallway. Stairs must be navigated to enter this condo. The bedrooms are on a split level.

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.

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.

Waterfront Beach Condo 5 min to AMI + Boat Dock

Welcome to your dreamy island getaway, on Palma Sola Bay! Just 2 miles from Anna Maria Island- Voted #6 most beautiful beaches in the US- & charming historic Bradenton. Your cozy condo backs up to an inviting pool & canal with boat dock and includes 2 free beach bikes. Nearby you will find amazing walking trails through mangroves, kayaking & bike riding to the beach or causeway. We are passionate hosts, with your best guest experience always in mind!