Townhome vacation rentals in Siesta Key

4.98 out of 5 average rating, 119 reviews

Townhouse in Anna Maria

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

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

A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.

4.93 out of 5 average rating, 55 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)!🏖

4.88 out of 5 average rating, 104 reviews

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.

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!

4.78 out of 5 average rating, 175 reviews

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.

Townhouse in Sarasota

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.

A heated community pool is surrounded by sun loungers, offering ample space for relaxation. Palm trees dot the background, and a white fence provides privacy. Bright sky and scattered clouds create a cheerful atmosphere, enhancing the overall sunny appeal of the area.

4.81 out of 5 average rating, 26 reviews

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.

An aerial view captures the vibrant neighborhood surrounding the vacation rental. Beach access is visible beyond the homes, along with a stretch of sandy shoreline and crystal-clear water. The layout shows various residential buildings and palm trees dotted throughout the area, creating a welcoming coastal atmosphere.

4.98 out of 5 average rating, 65 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.

The exterior of a waterfront townhome is depicted, featuring a light blue façade and an upper-level Juliet balcony. Palm trees are visible in the foreground, alongside a boat dock extending into the calm water. Reflections create a serene ambiance on the water's surface.

5 out of 5 average rating, 44 reviews

Great Times & Tan Lines

Make memories in your gorgeous waterfront townhome with 2 bedrooms and 1 ½ baths. An intimate community with 20 units ideally located 3 miles from the laid-back beach life of Anna Maria Island or 4 miles from the energy of downtown Bradenton and Manatee Riverwalk. Walk to Palma Sola Causeway Park and boat ramp where you rent paddle boards, jet skis, kayaks, plus horseback riding in the water. Relax at home, fish off the dock or watch for visiting manatees and stingrays.

An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.

4.99 out of 5 average rating, 157 reviews

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!

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, 196 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, 30 reviews

Townhouse in Sarasota

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

Popular amenities for Siesta Key townhouse rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly townhouse rentals

4.83 out of 5 average rating, 18 reviews

Sabal Key Haven - Heated Pool, Ideal Relaxation!

A vibrant living area features a bright blue sofa with a patterned throw and a green coffee table. Large glass windows allow natural light to fill the space, while two oversized pink chairs add a playful touch. Lush greenery is visible outside.

4.95 out of 5 average rating, 39 reviews

Art and Design in Bradenton Villa

Townhouse in Gillespie Park

A vibrant courtyard is filled with tropical plants, colorful lounge chairs, and a tiki bar. Unique garden decorations and a fish pond with a waterfall enhance the lively atmosphere. Striped umbrellas provide shade over the seating areas, creating a welcoming outdoor space.

4.95 out of 5 average rating, 377 reviews

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

A comfortable living area features a light-colored leather sofa and armchair, accentuated by blue decorative pillows. A wooden coffee table with decorative elements stands in the center, while a mirror and artwork add subtle interest to the walls. Natural light brightens the space.

5 out of 5 average rating, 3 reviews

Townhouse in The Cay Bradenton, FL + ANNA MARIA

4.8 out of 5 average rating, 276 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

4.85 out of 5 average rating, 170 reviews

A clear blue pool is surrounded by lounge chairs under orange umbrellas, offering a refreshing escape. Lush greenery and well-maintained landscaping enhance the tranquil environment. A path leads to a charming building with a red-tiled roof, while the nearby beach displays soft white sands and scattered beachgoers.

Townhouse in Sarasota

Our American Dream - A Paradise Destination

4.9 out of 5 average rating, 185 reviews

Mermaid Villa Gulf of Mexico Views

A heated pool is surrounded by lounge chairs and palm trees, creating a relaxing outdoor area. A shaded seating area is positioned nearby under an umbrella. Bright blue skies and greenery provide a serene backdrop to the pool space.

4.81 out of 5 average rating, 78 reviews

Anna Maria Island TH - close to beach, pool!

Townhouse rentals with a washer and dryer

5 out of 5 average rating, 7 reviews

Townhouse in Venice

Venice Island Escape • Steps to Beach • Workspace

A sheltered dining area is seen under a striped umbrella, featuring a large table surrounded by white chairs. A small heated pool is located nearby, complemented by lush greenery and colorful tropical plants lining the perimeter.

4.98 out of 5 average rating, 50 reviews

Siesta Sunrise-Just steps to the beach and village

4.67 out of 5 average rating, 3 reviews

Our House at the Beach Saltwater Retreat

The welcoming façade of the townhome is showcased, featuring a driveway lined with pavers and tropical landscaping. Tall palm trees and vibrant plants enhance the entrance, while large windows above the garage provide a glimpse of natural light within.

4.95 out of 5 average rating, 43 reviews

Walk to Beach & Village, Heated Pool Oasis

5 out of 5 average rating, 10 reviews

A spacious living area is depicted, featuring a light-colored sectional sofa with decorative pillows, a round coffee table, and a small dining area with a wooden table. Natural light fills the space through large windows, creating a bright and open environment.

Townhouse in Venice

Venice Cottage near Venice Beach

5 out of 5 average rating, 40 reviews

A bedroom is shown with lavender walls and natural light coming through the multi-pane window. A small white desk and chair are positioned in front of the window. A colorful piece of art is displayed on the wall, and a bed with a floral-patterned blanket is visible.

Townhouse in Cove

Walk to Beach & Marina | Beach Supplies | Near IMG

An enclosed lanai features a dining table with four chairs, ideal for relaxation. A decorative blue heron tapestry adorns the wall, while palm trees and a lagoon pond are visible through large sliding windows, enhancing the tranquil setting.

Townhouse in Bradenton Beach

4.8 out of 5 average rating, 10 reviews

Anna Maria Island - Gulf Get-A-Way at Runaway Bay

An outdoor dining area features a large table surrounded by wooden chairs, positioned on a balcony with a view of the sandy beach and ocean. Palm trees are visible, and beachgoers enjoy the water under clear blue skies.

4.65 out of 5 average rating, 26 reviews

Luxury 4 bedroom 4 bath Beachfront Home

Townhouse rentals with a patio

Townhouse in Longboat Key

A spacious bedroom features a large bed with white linens and decorative pillows. A comfortable green bench is positioned at the foot of the bed. Natural light fills the room through multiple windows adorned with bamboo shades, while a television and dresser complete the space.

4.84 out of 5 average rating, 44 reviews

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

A serene view of a sandy beach meets calm turquoise waters under a clear blue sky. Gentle waves lap at the shore, with soft grasses framing the sandy area, creating a peaceful and inviting atmosphere.

4.88 out of 5 average rating, 17 reviews

Miles of Sandy Island Beach

Townhouse in Bradenton Beach

A three-story duplex is visible, featuring a balcony on each level adorned with blue chairs. The ground floor includes a shared pool framed by lush greenery, with lounge chairs positioned around it. The exterior is painted in light colors, reflecting a coastal ambiance.

4.95 out of 5 average rating, 19 reviews

A Island Breeze Unit A

The exterior features a row of charming townhouse facades in soft pastel colors, framed by tall palm trees. A manicured pathway leads to the front doors, while landscaped shrubs and flowers add a natural touch to the inviting entryway.

4.94 out of 5 average rating, 51 reviews

Seas the Day

A serene pool area is surrounded by palm trees, with a curved shape and inviting blue water. Lounge chairs are positioned nearby for relaxation. The elevated house features a spacious balcony overlooking the pool, equipped with dining tables and chairs for outdoor enjoyment.

4.63 out of 5 average rating, 19 reviews

Pool Walk to the Village & Beach 3 bed 2 bath

5 out of 5 average rating, 13 reviews

Serenity at Sabal Key - Renovated Relaxing Comfort

5 out of 5 average rating, 39 reviews

Charming Townhome in Gated Community Near Beaches

An open living area showcases light purple walls and a contemporary kitchen with white cabinetry and stainless steel appliances. A glass dining table is set with a decorative box of red flowers and a bottle of champagne. A blue tufted sofa and a red accent chair provide comfortable seating.