Townhouse holiday rentals in Siesta Key

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.

4.94 out of 5 average rating, 396 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!

LocationFamilyPool

4.96 out of 5 average rating, 100 reviews

Townhouse in Anna Maria

Blue Jacaranda unit, Bean Point Beach 5 min walk

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

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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.

4.86 out of 5 average rating, 116 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.

ValueLocationIndoor spaces

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, 171 reviews

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.

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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.

5.0 out of 5 average rating, 48 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!

ValueFamilyComfort

5.0 out of 5 average rating, 26 reviews

Bradenton Beach 3BR | 2-Min Walk + Gulf Sunsets

Welcome to your dream getaway in Bradenton Beach on Anna Maria Island! This stunning 3BR/2.5BA home is just a 2-minute walk from the beach. Enjoy a heated communal pool with a spa for relaxation. Located under a mile from Historic Bridge Street, explore shops and entertainment easily. Unwind on two balconies with breathtaking sunset views over the Gulf. The fully stocked kitchen and provided beach essentials ensure a hassle-free stay. Experience the ultimate beach vacation!

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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.

4.79 out of 5 average rating, 214 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.

LocationFamilyCondition

4.98 out of 5 average rating, 40 reviews

3BED Home Siesta Key Beach

Escape to our family-friendly townhouse, only 15 min walk to the stunning Siesta Key Beach! Featuring 3 bedrooms and 2.5 bathrooms, our spacious townhouse ensures that everyone has their own comfortable space. The open living area is perfect for family gatherings, and the fully equipped kitchen lets you prepare delicious meals at your convenience. Book your family's vacation with us and create wonderful memories in this home away from home.

FamilyLocationBeach

4.96 out of 5 average rating, 102 reviews

Townhouse in Anna Maria

Wanderlust Villa

Welcome to Wanderlust Villa! This Anna Maria beachside beauty is a chic slice of paradise on AMI. Hues of pink and gold give the villa a warm and cozy yet ultra-chic vibe. Wanderlust Villa is a quick half-mile walk to the beach and a 10 minute walk to a variety of restaurant options. Your gulf-view sunsets are waiting for you! Any questions or booking requests outside of what is outlined please message!

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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, 58 reviews

Siesta Sunrise-Just steps to the beach and village

Location, location, location! Siesta Sunrise is just steps to beautiful Siesta Key beach and a short walk to the village. Enjoy this newly remodeled 2 bedroom 2.5 bath plus bonus room with sleeper sofa. Both bedrooms have en-suite baths with walk in showers. This property also features a heated pool shared between two units and each unit provides enough parking for two cars.

FamilyLocationAccuracy

4.84 out of 5 average rating, 238 reviews

Lovebirds’ Retreat | Steps to Siesta Key Beach

Romantic Honeymoon Suite 💕 Steps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beach, pool & gardens, central AC, and a heated lagoon-style pool for dreamy evening swims. Max 4 guests. Complimentary Wi-Fi, beach chairs & parking for 1 car make this the ultimate couples’ escape.

LocationFamilyParking

5.0 out of 5 average rating, 9 reviews

Salty Dog | Siesta Key Canal-Front Escape!

Salty Dog is a canal-front Siesta Key retreat just 2 minutes from the beach 🏖️ This 6BR luxury townhome features a private heated pool and spa, rooftop deck with beach views, shared dock with kayaks, and ping pong. Walk to Siesta Key Village, relax in spacious king suites, dog-friendly stays, and resort-style comfort for the whole family 🌊✨🐾

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Popular amenities for Siesta Key townhouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly townhouses

A refreshing pool is surrounded by lounge chairs and tropical greenery, offering a relaxing outdoor space. The vibrant blue exterior of the condo stands out against the palm trees, while beach access is visible in the background, ensuring proximity to the sandy shores.

4.97 out of 5 average rating, 98 reviews

The Perfect Beach Escape: Just a 1-Minute Walk!

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5.0 out of 5 average rating, 5 reviews

Chic Holmes Beach #A Private Pool

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A private pool is surrounded by a spacious patio, featuring lounge chairs and an outdoor seating area. Lush greenery adds a natural element, while the pool's clear water invites relaxation. The setting provides an ideal space for enjoying the outdoors in comfort.

5.0 out of 5 average rating, 16 reviews

Cast a Waves W/heated pool

FamilyLocationGetting around

4.88 out of 5 average rating, 17 reviews

Coastal Siesta Cottage | Walk to Siesta Key Beach!

LocationConditionPets

5.0 out of 5 average rating, 4 reviews

Our House at the Beach Townhouse

LocationParkingBeach

The spacious living area features a comfortable sectional sofa adorned with decorative pillows, a textured area rug, and a stylish coffee table. Natural light flows through large glass doors, connecting the indoor space to the outdoors. Open access to the kitchen and dining area enhances an inviting atmosphere.

5.0 out of 5 average rating, 78 reviews

Steps from the beach, private pool in Holmes Beach

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4.95 out of 5 average rating, 20 reviews

Near Lakewood Ranch w/pool in gated community

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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.

4.71 out of 5 average rating, 7 reviews

Charming Bungalow | Close to Beach | 2 Beds

ValueFamilySleep quality

Townhouse rentals with a washing machine and dryer

An aerial view showcases the proximity of Sunset Landings to the beach, with a clear pathway marked from the townhome to the white sandy shores. The vibrant turquoise waters and nearby boats are visible, while residential buildings line the street, indicating a welcoming community.

4.75 out of 5 average rating, 20 reviews

Beach View-Sunset Landings 4 by SeaBreeze Vacation

LocationFamilySleep quality

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.

4.82 out of 5 average rating, 85 reviews

Anna Maria Island TH - close to beach, pool!

LocationValueKitchen

4.67 out of 5 average rating, 3 reviews

Townhouse in Cortez

Palm Paradise

LocationAccuracyBeach

An open-concept living space features a comfortable sectional sofa with colorful cushions, a modern coffee table, and patterned area rugs. A light-filled kitchen and dining area are visible in the background, with a view of sliding glass doors leading to an outdoor space.

4.9 out of 5 average rating, 30 reviews

Sienna Retreat - Your Dream Getaway in Sarasota

LocationFamilyNearby

4.85 out of 5 average rating, 20 reviews

Sabal Key Haven - Heated Pool, Ideal Relaxation!

FamilyLocationComfort

4.88 out of 5 average rating, 74 reviews

Waterfront Beach Condo 5 min to AMI + Boat Dock

LocationFamilyLong stay

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, 186 reviews

Relaxing Retreat, King Bed, Beautiful Scenic Views

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Clear turquoise waters stretch towards the horizon, with gentle waves lapping against the pristine shoreline. The beach features soft, white sand and is bordered by low vegetation. A few distant figures can be seen enjoying the beach against a backdrop of cotton candy clouds.

Townhouse in Gulf Gate Estates

4.76 out of 5 average rating, 397 reviews

Coastal Retreat Near Siesta Key

LocationFamilyHospitality

Townhouses with a patio

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.

4.94 out of 5 average rating, 72 reviews

Getaway Family Beach Townhome w/Pool!

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5.0 out of 5 average rating, 14 reviews

1 of A Kind 3/2 Heart of UTC/Benderson area!

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Townhouse in Venice Beach

5.0 out of 5 average rating, 29 reviews

Venice Island Escape • Steps to Beach • Workspace

LocationFamilyAmenities

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.

5.0 out of 5 average rating, 12 reviews

Summer getaway near Siesta Key: Family Getaway

LocationSleep qualityKitchen

5.0 out of 5 average rating, 4 reviews

Townhouse in Parrish

Watters Row: Parrish Townhouse!

FamilyBeachQuiet

4.71 out of 5 average rating, 82 reviews

Townhouse in Lido Key

Charming Lido Beach Condo

FamilyLocationBiking

5.0 out of 5 average rating, 29 reviews

Serenity at Sabal Key - Renovated Relaxing Comfort

LocationFamilyLong stay

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.