Townhome holiday rentals in Siesta Key

5 out of 5 average rating, 3 reviews

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

Townhouse in Holmes Beach

4.91 out of 5 average rating, 45 reviews

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)!🏖

Guest favourite

Townhouse in Gillespie Park

4.95 out of 5 average rating, 371 reviews

Peacock🦚1/2 m Walk to Downtown #TheTropicalNut ☀️🥳👙

You are safe with me!Enhanced cleaning protocol in place- as per Airbnb guidelines. Welcome! Be yourself! A five star stay, guaranteed. You WILL be happy here! Special occasion? My favorite. I like doing special things for special people. Courtyard w/ lounge chairs, tiki bar, pond & cafe seating! Queen bed and a pullout couch with new mattress! A 1/2 m walk to downtown. 1 of 2 upstairs apartments at The Tropical Nut! We aim to please! No-regret-booking! Will consider-if asked-pets of all kinds!

Guest favourite

Townhouse in Laurel Park

4.88 out of 5 average rating, 286 reviews

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park area! Walk/bike to historic downtown Sarasota with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the screened lanai and fenced backyard for privacy . Cook out on the gas grill, enjoy a cup of coffee or your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk and check out the many historic homes in the area. Enjoy the sunsets!

Townhouse in Holmes Beach

5 out of 5 average rating, 41 reviews

Golf Cart, Coffee Bar, 2 Blocks to Beach, Luxe

!!6-Seater Electric Golf Cart INCLUDED!! Stay 7+ nights between September 7th - September 20th, 2025 and the luxe 6 seater golf cart will be included in your rental for free!! Why you'll love staying here: Two blocks from the beach, private screened porch, 6-seater golf cart, community pool, fully stocked kitchen, luxe bedding, thoughtful amenities, all meticulously maintained. ☀ 5 minute walk to the beach ☀ 5 minute drive to Pine Ave. shopping & dining ☀ 15 minute drive to Bradenton

4.79 out of 5 average rating, 165 reviews

Townhouse in Sarasota

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.

4.97 out of 5 average rating, 33 reviews

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.

5 out of 5 average rating, 71 reviews

Townhouse in Bradenton

Heated Community Pool Townhome• Near Beach & Shops

Welcome to your vacation home! • 2 queen and 1 king size beds • Each bedroom has smart TV and bathroom • High chair and pack-n-play • Stunning lake view from screened lanai • 5 min walk to shops and restaurants nearby • 25 minutes to most stunning Florida beaches (beach chairs included) • Plus our gated secured community includes heated pool, playground, tennis, basketball, and volleyball courts. Start your perfect vacation today! Absolutely no smoking!

Guest favourite

5 out of 5 average rating, 7 reviews

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!

4.73 out of 5 average rating, 37 reviews

Canal Lower-Gorgeous 3 bed 3 bath near SK Village

This 3BR/3BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? We are just minutes away from Siesta Key Beach, voted the # 1 beach in the U.S! Steps to the village for shopping and restaurants. The semi-private heated pool and hot tub is shared with the upper unit. Step outside & you’ll find a quaint outdoor area featuring a tranquil pool, hot tub, and BBQ: perfect for family gatherings!

4.78 out of 5 average rating, 192 reviews

Siesta Key Beach House with Private Beach Access

Great vacation location on beautiful Siesta Key (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.