Waterfront holiday rentals near Siesta Beach

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.89 out of 5 average rating, 138 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

4.94 out of 5 average rating, 132 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

A serene beach scene is captured with gentle waves lapping against the shore. The clear water displays various shades of blue and green, while a sandy coastline extends into the distance. People can be seen enjoying the beach, with a bright blue sky overhead.

4.9 out of 5 average rating, 153 reviews

Sea Club II Garden House

This surprisingly spacious 1200sf beach bungalow has been completely renovated in February 2020 from floor to ceiling. You will enjoy 3 spacious bedrooms with a private Master suite, spacious updated eat in kitchen and large family room. The unit is unique with a private deck to relax on at night. Walking distance to private beach access as well as a newly renovated heated salt water Community pool (Shared) on the intercoastal with breath taking views. This is a one of a kind experience.

4.9 out of 5 average rating, 119 reviews

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!

The enclosed Lanai features large bay windows showcasing views of the Gulf of Mexico. A seating area includes wicker chairs and a coffee table. Light-colored walls are contrasted by wooden accents and a ceiling fan, creating a bright and airy atmosphere.

4.94 out of 5 average rating, 127 reviews

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

Apartment in Longboat Key

4.98 out of 5 average rating, 229 reviews

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

4.93 out of 5 average rating, 137 reviews

Siesta Key condo, beach access, heated pool

This condo is set in the perfect location between the beach and the bay! Soak up the sun at the heated pool, enjoy the tiki bar, or try your luck fishing on the pier, all while viewing the boats on the intercoastal! Included is private deeded beach access that is just a easy 5 min walk. Hop on the free trolley right outside your door to go to Siesta Key Village with plenty of restaurants, bars and shops only .5 miles away. 65" tv free wifi Netflix Disney+. Boat slip available up to 24'

4.98 out of 5 average rating, 105 reviews

The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.

Home in Bradenton Beach

Gulf Front! Beach Views!+ Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 369 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.97 out of 5 average rating, 117 reviews

Palm Bay Club! Resort Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

A heated pool is surrounded by lounge chairs set on a white deck, with palm trees and lush greenery nearby. A multi-story building looms in the background, along with a tennis court visible at the side. A safety sign is placed by the gated entry.

4.89 out of 5 average rating, 112 reviews

Siesta Key Beach (OHAB) Townhouse #1 beach

Two bedroom townhouse directly across main part of Siesta Key beach. Large open living area. 65” curved cable tv. Internet. 1400SF. Living area. Heated pool, large pavilion area with grill and tables to accommodate large groups. Tennis courts directly out front door. Newly remodeled kitchen and master bath. Beach chairs, toys and beach cart available. Balconies front and back. Plenty of parking.. 15 minute walk to many local.restaurants .

Popular amenities for waterfront rentals near Siesta Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.91 out of 5 average rating, 138 reviews

Flat in Bradenton Beach

Newly Remodeled Beachfront Studio - On the sand!

4.98 out of 5 average rating, 132 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Flat in Bradenton

Sweet Retreat at Shorewalk!

4.78 out of 5 average rating, 114 reviews

Flat in St. Pete Beach

Pass a grille Gulf Way Beachfront Parking WiFi 13

4.96 out of 5 average rating, 116 reviews

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

Flat in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

5 out of 5 average rating, 20 reviews

Siesta Beachfront Suite

4.97 out of 5 average rating, 441 reviews

A serene view of the Manatee River showcases calm waters reflecting the sky. Lush greenery surrounds the area, accompanied by a covered dock nearby. An American flag flutters gently, and a hint of a charming structure with a porch is visible to the right.

Flat in Ellenton

Serenity on the Manatee

The open living space is highlighted by a circular dining table surrounded by four chairs. A turquoise sofa and coffee table are arranged in the living area, with a large TV mounted on the wall. Natural light fills the room through nearby windows, enhancing the airy atmosphere.

4.79 out of 5 average rating, 243 reviews

2/2 Beach House Apt on Siesta Key

A large heated swimming pool is visible in the foreground, surrounded by lounge chairs and umbrellas. The water appears inviting under a clear blue sky, with a view of the inter-coastal waterway in the background. Tropical vegetation adds to the serene atmosphere.

4.7 out of 5 average rating, 190 reviews

Siesta Key Condo. Sit by the water !

Waterfront house rentals

5 out of 5 average rating, 100 reviews

A spacious outdoor living area is shown, featuring a seating arrangement with floral-patterned cushions and a wooden coffee table. A dining table, set for six, is positioned nearby. The screened lanai offers views of the pool, surrounded by greenery and clear blue skies.

Home in Bradenton

NEW Saltwater Pool + Spa | Mins to AMI Beaches/IMG

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

4.77 out of 5 average rating, 542 reviews

Beachfront Getaway in Siesta Key

A heated pool is framed by a screened enclosure, allowing for sunlit swims while providing shade. Comfortable lounge chairs are lined along the poolside, and greenery is visible in the background, creating a serene atmosphere for relaxation.

4.94 out of 5 average rating, 111 reviews

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

4.86 out of 5 average rating, 138 reviews

Home in Longboat Key

Summer House longboat key

4.85 out of 5 average rating, 104 reviews

Stylish & Bright: Steps to Beach ~ Pool ~ Hot Tub!

4.96 out of 5 average rating, 24 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

An inviting living area features a spacious sectional sofa adorned with vibrant pillows and a cozy fireplace. Large glass doors provide natural light and views of the outdoor pool area, while a unique coffee table complements the mid-century modern design.

5 out of 5 average rating, 10 reviews

Mid-Century Modern, Pool, Mins to Siesta Key Beach

A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.

4.89 out of 5 average rating, 106 reviews

Oceanfront home w/sunset views of Sarasota Bay

Waterfront apartment rentals

The image captures a vibrant sunset over the horizon, casting warm hues across the sky. Palm trees line the foreground, creating a tropical ambiance. The view also includes a peaceful road and glimpses of the beach beyond, emphasizing the proximity to coastal scenery.

4.96 out of 5 average rating, 53 reviews

Siesta Key Beach front 2 bedroom condo w/ parking

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 191 reviews

Private Beach & Intracoastal Waterfront

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

4.95 out of 5 average rating, 171 reviews

A cozy bedroom features a large green bed with multiple white pillows, complemented by two bedside lamps. The ceiling showcases a tropical leaf pattern, and mirrors adorn the walls. Natural light enters through a window, with white curtains framing the view.

Apartment in Bradenton

KING bed + Anna Maria Island Beaches + Beach Gear!

Apartment in Longboat Key

4.88 out of 5 average rating, 127 reviews

Sunset and beach view from your balcony Unit 403

4.88 out of 5 average rating, 176 reviews

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

Apartment in Sarasota

Lake View 1BR Condo | Heated Pool Near Siesta

Apartment in Bradenton Beach

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

4.99 out of 5 average rating, 169 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

4.78 out of 5 average rating, 101 reviews

Beachwalk Townhouse with view of Gulf of Mexico

Other waterfront holiday rentals

4.88 out of 5 average rating, 106 reviews

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.

Townhouse in Siesta Key

Siesta Key - Private Beach Access - 2BR Retreat

Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.

4.98 out of 5 average rating, 53 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

A bright living area features a spacious white sofa centered beneath a large woven light fixture. Tropical plants are situated near large windows that allow natural light to fill the space. A neutral rug complements the light-colored furniture and decor.

4.93 out of 5 average rating, 40 reviews

Coastal Retreat near Siesta Key Beach and Downtown

A spacious living area features modern furniture arranged for comfort and relaxation. Large windows provide abundant natural light and views of the waterway. A light-toned coffee table sits in the center, complemented by soft cushions on the sectional sofa. The dining space is visible in the background.

5 out of 5 average rating, 5 reviews

Siesta Key 4BR Waterfront Escape • Spa/Dock Access

4.97 out of 5 average rating, 74 reviews

A serene bedroom featuring a spacious bed with light bedding. Natural light pours in through two windows, illuminating the room's wooden beams and soft green paneling. A small table with a lamp and decorative items completes the inviting space.

Home in Myakka City

"Little Siesta" - Farm home near Terra Nova

5 out of 5 average rating, 31 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

4.83 out of 5 average rating, 52 reviews

A spacious balcony is showcased, featuring a dining table with six chairs. The area is surrounded by a white railing, with views of palm trees and a vibrant sky during twilight. Large sliding glass doors lead into the interior, creating a seamless connection.

Apartment in Sarasota

Beach Front Haven