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Places to stay near Siesta Key Watersports

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Top-rated holiday rentals near Siesta Key Watersports

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

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Superhost
Home in Gulf Gate Estates

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Welcome to The Salty Unicorn, your cheerful Sarasota escape just five miles from Siesta Key Beach. This fully renovated 3-bedroom home is designed for relaxation and fun, with a bright open layout, stylish coastal décor, and plenty of space to gather with family or friends. Start your mornings with coffee by the pool, spend sunny afternoons swimming or lounging in the spacious backyard, and end the day with dinner in the screened lanai. Whether you’re here for beach days, family time, or a peace

4.89 out of 5 average rating, 107 reviews
Superhost
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.
Apartment in Siesta Key

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!

4.88 out of 5 average rating, 146 reviews
Top guest favourite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

4.94 out of 5 average rating, 100 reviews
Top guest favourite
A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.
Home in Sarasota

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

4.98 out of 5 average rating, 119 reviews
Guest favourite
An outdoor seating area features a rectangular table surrounded by four chairs, all set on a patterned rug. Two cushioned lounge chairs are positioned beside a large umbrella. A BBQ grill and greenery are visible in the spacious, fenced backyard.
Home in Gulf Gate Estates

Beachside Bliss: Family Paradise/Siesta Key3BR/2BA

Escape to this stunning, fully renovated 3BR/2BA home in the prestigious Gulf Gate Neighborhood, just 5 minutes from Siesta Key Beach – ranked the #1 beach in the U.S.! This spacious and airy retreat is designed for relaxation and making unforgettable memories. Enjoy an impeccably styled interior, modern amenities, and a prime location close to Sarasota’s best attractions. Indulge in top-rated restaurants, vibrant shopping centers, and endless beachside adventures—all just around the corner

4.95 out of 5 average rating, 130 reviews
Guest favourite
An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.
Home in South Sarasota

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

4.97 out of 5 average rating, 218 reviews
Top guest favourite
Home in Sarasota

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

4.95 out of 5 average rating, 198 reviews
Guest favourite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Apartment in Siesta Key

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

4.85 out of 5 average rating, 110 reviews
Guest favourite
Guest suite in Sarasota

Sweet, pet friendly Siesta Suite

Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.

4.89 out of 5 average rating, 209 reviews
Top guest favourite
An inviting living area features a blue sofa with decorative pillows, complementing a rustic wooden coffee table. A mounted Smart TV displays the Netflix logo. Bright pink LED lights illuminate the ceiling, enhancing the compact kitchen area, which includes bar stools and stylish cabinetry.
Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

4.95 out of 5 average rating, 421 reviews
Top guest favourite
A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.
Home in Gulf Gate Estates

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Walking distance to a Publix grocery store and 5 good restaurants. ⅕1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. New tile and wood floors throughout. Quite neighborhood for walking .

4.96 out of 5 average rating, 277 reviews
Top guest favourite
Flat in Sarasota

Modern 1BR Near Siesta Key + Private Parking

Private coastal retreat minutes from Siesta Key Beach. This spacious 950 sq ft upstairs apartment features soaring ceilings, a bright open layout, and a private entrance. Enjoy a king-sized bed, full kitchen, in-unit washer and dryer, fast Wi-Fi, and dedicated parking. Perfect for couples or guests seeking a peaceful, comfortable stay near the beach. Consistently rated 5⭐ for cleanliness, comfort, and communication. Ideal for couples seeking a peaceful, comfortable beach stay.

5.0 out of 5 average rating, 275 reviews

Popular amenities for holiday rentals near Siesta Key Watersports

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Siesta Key Watersports

Siesta Key Watersports

45 locals recommend

Phillipi Estate Park

28 locals recommend

Mazzone Olive Oil

5 locals recommend

Apartment rentals with wifi

Top guest favourite
A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.
Apartment in Siesta Key

Breathtaking Beachfront Views in Siesta Key

5.0 out of 5 average rating, 103 reviews
Top guest favourite
Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

4.92 out of 5 average rating, 170 reviews
Top guest favourite
A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.
Apartment in Siesta Key

Heated Pools & Spa · Private Beach + Bay Views

4.97 out of 5 average rating, 137 reviews
Guest favourite
The studio features a modern kitchen with white cabinetry and a large countertop. A flat-screen TV is mounted on the wall, and natural light enters through sliding glass doors that lead to the private garden. A compact dining table and a plush blue ottoman add functionality.
Apartment in Gulf Gate Estates

Modern Studio · 5 min from Siesta Beach

4.95 out of 5 average rating, 153 reviews
Guest favourite
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.
Apartment in Siesta Key

Sarasota Surf & Racquet Club Siesta Key Condo

4.83 out of 5 average rating, 150 reviews
Guest favourite
Apartment in Siesta Key

Beachwalk Townhouse with view of Gulf of Mexico

4.79 out of 5 average rating, 109 reviews
Guest favourite
Apartment in Siesta Key

The Flamingo's Nest at Sea Club II

4.94 out of 5 average rating, 156 reviews
Top guest favourite
An entry gate is featured, adorned with elegant wrought ironwork, leading into the well-maintained grounds of the property. Surrounding foliage is visible, contributing to a serene atmosphere. The address number is displayed on the adjacent wall, while a sign indicating 'Siesta Gardens' is prominently placed.
Apartment in Siesta Key

Siesta Gardens @ Siesta Key Village

4.97 out of 5 average rating, 448 reviews

Family-friendly house rentals

Top guest favourite
Home in Siesta Key

Heated pool & Infrared Sauna, 2 min to beach

4.98 out of 5 average rating, 101 reviews
Guest favourite
Home in Siesta Key

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

4.91 out of 5 average rating, 129 reviews
Top guest favourite
A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.
Home in Siesta Key

Siesta Key Beach & Village 2BR/2BA Steps to Beach

4.93 out of 5 average rating, 168 reviews
Guest favourite
A heated pool is enclosed within a screened area, surrounded by lush greenery and outdoor seating. The pool area features a natural stone deck, with lounge chairs positioned for sunbathing. The peaceful environment offers a private retreat for relaxation and enjoyment.
Home in Sarasota

Heated Pool - Just 1 mile to Beach! Updated/Fun!

4.92 out of 5 average rating, 124 reviews
Guest favourite
Home in Sarasota

Sun-filled cottage with pool, walk to beach

4.96 out of 5 average rating, 112 reviews
Guest favourite
A spacious backyard is shown at sunset, featuring a heated pool surrounded by a tiled patio. Tropical palm trees frame the area, and a tiki bar can be seen in the background. Soft outdoor lights create a welcoming ambiance as the sky fills with vibrant orange and purple hues.
Home in Sarasota

The Sand Castle - Backyard Oasis Mins from Siesta!

4.94 out of 5 average rating, 168 reviews
Guest favourite
A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.
Home in South Sarasota

The Mango House Beach Cottage

4.98 out of 5 average rating, 149 reviews
Top guest favourite
Home in Gulf Gate Estates

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

4.96 out of 5 average rating, 134 reviews

Apartment rentals with air conditioning

Top guest favourite
A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.
Flat in Arlington Park

Studio Minutes to Siesta key, Lido Key, and SMH!

4.97 out of 5 average rating, 240 reviews
Top guest favourite
Flat in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

4.94 out of 5 average rating, 142 reviews
Superhost
Flat in Siesta Key

Elegant 2BR + Den | Heated Pool | Near Beach

4.79 out of 5 average rating, 205 reviews
Top guest favourite
A private balcony is showcased with two white lounge chairs and a small table. Lush palm trees provide greenery, while a heated pool can be seen beyond the railing. Sunlight filters through the trees, creating a serene outdoor space.
Flat in Sarasota

Beechwood Suites B

4.99 out of 5 average rating, 108 reviews
Guest favourite
A spacious sleeping area features a queen-size bed with a light blue patterned bedspread. A cozy armchair is positioned beside the bed, and window treatments allow natural light to brighten the room. Light wood flooring complements the neutral-toned walls.
Flat in Lido Key

Lido Key FL Studio/Efficiency 5

4.84 out of 5 average rating, 147 reviews
Guest favourite
Flat in Downtown Sarasota

Central Downtown Apartment with Pool and Gym

4.87 out of 5 average rating, 206 reviews
Guest favourite
Flat in Siesta key

· King bed . Pool. Daily rentals

4.85 out of 5 average rating, 385 reviews
Superhost
A modern living area displays a bold palm-patterned accent wall with a mounted television. Two stylish lounge chairs are positioned nearby, accompanied by a small indoor plant on a decorative table. The open layout leads to a bright and airy kitchen area.
Flat in Sarasota

Funky & Fun Apartment in Central SRQ

4.9 out of 5 average rating, 146 reviews

Other great holiday rentals near Siesta Key Watersports

Top guest favourite
Guest suite in Sarasota

Siesta Keys stylish and affordable Airbnb.

4.91 out of 5 average rating, 396 reviews
Top guest favourite
A stunning pool area is surrounded by lush greenery and tropical plants. A prominent rock feature with multiple waterfalls is visible, providing a serene focal point in the outdoor space. The vibrant blue water complements the natural elements, creating a tranquil retreat.
Island in Sarasota

SEPT SALE! Sarasota #1 Luxury Villa! PRIV BEACH!

4.98 out of 5 average rating, 367 reviews
Top guest favourite
A modern kitchen is presented with warm wooden cabinetry and stainless steel appliances. A large island provides seating with two white stools. Sunlight illuminates the space through a window above the sink, where a bouquet of flowers adds a vibrant touch.
Home in Sarasota

Siesta Breeze ~ Charming Coastal Cottage

4.99 out of 5 average rating, 140 reviews
Top guest favourite
A screened lanai features a bubbling hot tub and comfortable seating area adorned with neutral-colored cushions. Soft lighting is offered by overhead string lights. Surrounding greenery enhances the peaceful ambiance, while large windows allow natural light to flow into the space.
Home in Sarasota

Turtle Nest Oasis • Hot Tub • 5 mi to Siesta Key

5.0 out of 5 average rating, 207 reviews
Superhost
Bungalow in South Sarasota

New listing: Coastal Retreat 7-mins to Siesta Key

5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Sarasota

siesta breeze paradise suite

5.0 out of 5 average rating, 32 reviews
Top guest favourite
A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.
Home in Sarasota

The Palms Away

5.0 out of 5 average rating, 38 reviews
Top guest favourite
Bungalow in Sarasota

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

5.0 out of 5 average rating, 11 reviews