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Waterfront vacation rentals in Siesta Key

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Top-rated waterfront rentals in Siesta Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A sandy pathway leads through lush greenery, providing access to a charming two-story building. The structure features a spacious balcony, surrounded by palm trees and local vegetation, under a bright blue sky with scattered clouds.

Apartment in Longboat Key

4.95 out of 5 average rating, 103 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

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.

Condo in Siesta Key

4.9 out of 5 average rating, 120 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.

Condo in Siesta Key

4.93 out of 5 average rating, 113 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 spacious bedroom features a large bed with a blue quilt, flanked by two bedside tables with lamps. Sliding glass doors open to a private deck, allowing natural light to flood the room. Soft blue walls complement the light-colored flooring.

Condo in Siesta Key

4.83 out of 5 average rating, 300 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

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.

Home in Siesta Key

4.9 out of 5 average rating, 145 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.

An aerial view showcases a private island surrounded by water, featuring lush greenery and two tiny homes. A manicured lawn is visible with seating areas, umbrellas, and pathways that create a serene outdoor environment.

Tiny home in Sarasota

4.89 out of 5 average rating, 222 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

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.

Apartment in Siesta Key

4.93 out of 5 average rating, 111 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!

The modern kitchen features white cabinetry and a spacious island with seating for four. Stainless steel appliances are visible, including an oven, microwave, and refrigerator. Stylish pendant lights hang overhead, illuminating the area. A neutral tile backsplash adds a clean, contemporary touch.

Condo in Siesta Key

4.94 out of 5 average rating, 123 reviews

Seaside Sanctuary

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'

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.

Condo in Siesta Key

4.91 out of 5 average rating, 127 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

Post Hurricane- Complex OPEN Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 265+ reviews that ave FIVE STAR!

Top guest favorite

A charming cottage is depicted with light blue wooden siding and white accents. The front yard is gravelled, surrounded by landscaping featuring mature trees and shrubs. A welcoming porch with a railing leads to the main entrance, enhancing the property's inviting look.

Home in Siesta Key

5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

FULLY RESTORED POST HURRICANE! HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time and post hurricane updates! If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Top guest favorite

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.

Condo in Siesta Key

4.97 out of 5 average rating, 321 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. Enjoy 2 free bikes day rental with booking!

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.

Condo in Siesta Key

4.88 out of 5 average rating, 102 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 .

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Siesta Key waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

A spacious bed is centered in the room, layered with neutral-colored bedding and decorative pillows featuring floral patterns. Flanking the bed are two bedside tables topped with lamps, and a large piece of artwork depicting a beach scene hangs above.

Apartment in Bradenton Beach

4.9 out of 5 average rating, 127 reviews

Newly Remodeled Beachfront Studio - On the sand!

Top guest favorite

An outdoor balcony area is depicted, featuring a small table and two chairs overlooking a sandy beach and the Gulf of Mexico. Sunlight reflects off the water, and palm trees are visible in the background, creating a serene coastal view.

Apartment in Longboat Key

5 out of 5 average rating, 9 reviews

Sunset and Beach view unit 402

Top guest favorite

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.

Apartment in Bradenton

4.97 out of 5 average rating, 100 reviews

Sweet Retreat at Shorewalk!

A broad view of Siesta Beach reveals soft white sands and vibrant blue waters, with various beachgoers enjoying the sun. Colorful umbrellas and beach tents are scattered along the shore, and several groups can be seen lounging on towels. The tranquil ocean meets the coastline seamlessly.

Apartment in Siesta Key

5 out of 5 average rating, 28 reviews

Good Vibrations - stay ON the beach in Siesta Key!

A heated swimming pool is surrounded by a paver sun deck featuring loungers and chairs in various colors. Lush greenery and palm trees provide a natural backdrop, creating a relaxed atmosphere. The pool's water is calm and inviting, reflecting the sky above.

Apartment in Sarasota

4.75 out of 5 average rating, 321 reviews

King bed. Pool. Daily rentals

A dining table showcases a glass top with intricately woven placemats. Each setting features decorative plates and neatly folded napkins secured with decorative rings. Sheer curtains frame the window, offering glimpses of lush palm trees outside.

Apartment in Bradenton Beach

4.88 out of 5 average rating, 223 reviews

Las Palmas Beach Rentals Unit 1

Top guest favorite

A stunning sunset over the Manatee River is captured, highlighting vibrant hues of orange, pink, and purple reflected in the calm water. A wooden dock extends into the river, creating a peaceful focal point against the colorful sky.

Apartment in Ellenton

4.96 out of 5 average rating, 397 reviews

Serenity on the Manatee

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.

Apartment in Siesta Key

4.69 out of 5 average rating, 184 reviews

Siesta Key Condo. Sit by the water !

Waterfront house rentals

Top guest favorite

Home in Bradenton Beach

4.99 out of 5 average rating, 72 reviews

Beach front! Sunsets + Bridge Street+ Restaurants!

A serene outdoor area features two lounge chairs beside a small table, surrounded by lush palm trees. The clear water of the canal reflects the blue sky, while a screened enclosure contains a swimming pool nearby, creating a tranquil setting for relaxation.

Home in Sarasota

5 out of 5 average rating, 15 reviews

Water's Edge: Charming Canal Oasis

A spacious living area features blue leather sofas arranged around a plush blue pouf. Natural light enters through large windows, illuminating the terracotta tiled floor. A wooden staircase leads to an upper level, while a surfboard decorates the wall, adding a coastal touch to the space.

Home in Anna Maria

4.9 out of 5 average rating, 10 reviews

Bayfront Beach access with Heated Pool!

A shared outdoor area features a sparkling blue pool surrounded by lounge chairs. The building showcases a modern design with a light-colored facade and a wraparound deck for relaxation, complemented by palm trees and bright red umbrellas that add a pop of color.

Home in Siesta Key

4.9 out of 5 average rating, 105 reviews

Spacious & Modern Gem ~ Walk to Gated Beach ~ Pool

Top guest favorite

A spacious garage is visible, featuring paddleboards, a ping pong table, and various outdoor equipment. Two beach cruiser bikes with light blue frames and brown accents are positioned in front, adding a beachy touch to the inviting environment.

5 out of 5 average rating, 9 reviews

Beach Retreat! Bikes, Paddleboards, Sauna & more!

Top guest favorite

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

Home in Holmes Beach

5 out of 5 average rating, 29 reviews

Heated pool, 3-Story bay views, 5min walk to beach

A spacious kitchen area features sleek cabinetry and a large center island with a striking stone surface. Wooden beams add a rustic touch overhead, while modern appliances are seamlessly integrated. Natural light floods the space, creating an inviting environment for meal preparation and gathering.

Home in Siesta Key

5 out of 5 average rating, 3 reviews

Rustic Sands - 650

A clear view of the inviting swimming pool is presented, bordered by lounge chairs with red and white stripes. Palm trees sway gently in the background, framing the scenic vista of Sarasota Bay and lush greenery beyond.

Home in Sarasota

4.78 out of 5 average rating, 9 reviews

Bayfront Beauty: Heated Pool, King size Bed

Waterfront condo rentals

A bright living area features large floor-to-ceiling windows that allow natural light to fill the space. A light-colored sectional sofa and a modern coffee table are present, along with a floor lamp. A balcony is visible in the background, showcasing views of greenery.

Condo in Siesta Key

4.91 out of 5 average rating, 44 reviews

Beach Haven on Siesta Key Beach

A clear view of the ocean is presented, complemented by lush greenery in the foreground. Buildings line the coastline, and a blue sky with light clouds enhances the scene, creating an atmosphere of tranquility and connection to nature.

Condo in Siesta Key

4.95 out of 5 average rating, 21 reviews

Penthouse Expansive Ocean Views

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.

Condo in Siesta Key

4.85 out of 5 average rating, 175 reviews

Best Siesta Key Condo

A light-colored bedroom features a spacious bed with a patterned comforter, complemented by a white dresser and a large television. Soft blue walls enhance the serene atmosphere. A ceiling fan and a door lead to an adjacent bathroom, adding convenience to the space.

Condo in Siesta Key

4.8 out of 5 average rating, 83 reviews

Cozy Gem on Siesta Key – Nice Walk to Beach & Bay!

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.

Condo in Siesta Key

4.98 out of 5 average rating, 41 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

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.

Condo in Siesta Key

4.82 out of 5 average rating, 136 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

4.92 out of 5 average rating, 178 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Top guest favorite

A dining area is visible with a wooden table surrounded by blue upholstered chairs. Large windows offer views of the beach and turquoise waters, providing a bright, airy atmosphere enhanced by natural light. Coastal-themed artwork adorns the wall, complementing the serene beach scenery.

Condo in Sarasota

5 out of 5 average rating, 48 reviews

Breathtaking Beachfront Views in Siesta Key

Quick stats about waterfront rentals in Siesta Key

Total rentals
350 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
290 properties have a pool

Destinations to explore