Townhome holiday rentals in Sarasota County

A charming bungalow is framed by lush greenery and palm trees. The inviting front porch features white furniture, while a manicured lawn enhances the home's curb appeal. A driveway leads to a garage, completing the welcoming exterior of this designer home.

5 out of 5 average rating, 4 reviews

Charming Bungalow | Close to Beach | 2 Beds

The Sandy Starfish is a newly decorated coastal bungalow just a short walk from the powdery sands of Siesta Key, ranked the #1 beach in the USA. Designed for comfort and charm, this two-bedroom retreat features a bright living area with Smart TV, a fully equipped kitchen, and whimsical handcrafted décor throughout. Relax with a glass of wine on the covered front porch, share meals in the stylish dining space, or enjoy sunny afternoons in the spacious backyard. With a king bedroom, a queen bedroo

An open-concept living area features light-colored leather seating arranged around a glass coffee table. Large sliding doors provide access to a waterfront balcony, allowing natural light to fill the space. Decor includes a blue area rug and coastal-themed artwork, enhancing a serene ambiance.

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

4.8 out of 5 average rating, 281 reviews

A serene house exterior is presented, featuring a light-colored façade, a front door framed by lush greenery, and a driveway leading to a garage. Colorful flowers and plants line the walkway, complemented by a partly cloudy sky.

Townhouse in North Port

Entire Guest Suite with Private Entrance & Lanai

One-level private house. The Guest Suite has the lanai and private entry from the sidewalk! You'll love staying here. Green, Quiet area, with a lot of trees, plants, and flowers around the house. You'll hear the birds singing, and see absolutely friendly rabbits. Very convenient location. Easy access to I-75 and 41-US. Water Park, Golf courses, famous Warm Mineral Springs. Incredible beaches around 30 min. Jet Ski, kayak, and fishing. Shopping centers, grocery stores, restaurants, and cafes.

A comfortable living area showcases a gray sofa with decorative cushions and a round coffee table at its center. Two accent chairs are positioned nearby. A dining table for four is visible, with large sliding glass doors providing natural light and views of the outdoor area.

4.88 out of 5 average rating, 105 reviews

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.

The exterior of a modern two-story condo building is displayed, featuring light blue siding and white accents. Paved pathways lead to individual garages, bordered by neatly manicured landscaping. A clear sky with a few clouds is visible above, enhancing the bright and inviting appearance of the area.

5 out of 5 average rating, 7 reviews

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!

A serene view of Siesta Key Beach is captured, showcasing soft white sands and gentle turquoise waves. Palm trees frame the scene, and various beach umbrellas are visible in the distance, hinting at a lively beach atmosphere under a clear blue sky.

5 out of 5 average rating, 45 reviews

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!

A serene view of the intercoastal waterway is captured, featuring calm waters reflecting the sky. Lush greenery lines the opposite shore, while a wooden dock extends into the water. Palm fronds frame the scene, emphasizing the tranquil coastal environment.

4.78 out of 5 average rating, 176 reviews

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.

An aerial view reveals the vibrant community surrounding this vacation rental, with colorful buildings and lush palm trees. The coastline stretches in the distance, showcasing the beach's sandy shoreline and turquoise waters, while the local neighborhood features a mix of residential and commercial structures.

4.98 out of 5 average rating, 54 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.

Townhouse in Port Charlotte

4.96 out of 5 average rating, 55 reviews

Nearby golfing, fishing, dining, spring training

Escape to this new, comfortable and practical side by side duplex featuring 3 bedrooms and 2 bathrooms, perfect for up to 6 guests! Your home is private, the only shared space is the patio & pool area Near Golf courses -7 minutes to Rays spring training -Charlottes sports park - 2 miles to town center - 6 miles from beautiful Beachfront Park -5 minutes to Centennial Rec. center Pool, Themed walls, Fully stocked kitchen, BBQ grill! Catch excitement of spring training!

A beach scene features a colorful umbrella providing shade over a beach chair and cooler. Soft, white sand stretches along the shoreline, meeting the calm, turquoise waters under a clear blue sky with minimal clouds.

4.78 out of 5 average rating, 197 reviews

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.

4.73 out of 5 average rating, 33 reviews

2BR/4BA Pool view townhouse 250 yards to the beach

Beautiful home with heated POOL! New flooring! Brand new shower on the lower level, 3 mins walk to the famous Crescent Beach! 2 bedrooms upstairs, 2 full baths, 2 half baths, GARAGE, FREE WI-FI, WASHER/DRYER, TV, skim boards, beach toys, chairs, books, board games, screened porch, balcony! Everything you need to enjoy your stay in PARADISE! For extra guests please use a pull out sofa on the mail level. Max 6 people

A two-story building is surrounded by lush greenery and white sand landscaping. Palm trees provide shade, while vibrant plants add color to the scene. The entrance features a bright door, with stairs leading up to the balcony area, enhancing the welcoming residential vibe.