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Vacation rentals in Sarasota Beach

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Top-rated vacation rentals in Sarasota Beach

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Top guest favorite

A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.

Condo in Siesta Key

5 out of 5 average rating, 126 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach Accessories • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

Lounge chairs with decorative blue cushions are arranged on a patio, overlooking a serene body of water. A lush green lawn extends in front of the water, and the sky is tinted with soft hues of orange and pink from the setting sun.

Home in Sarasota

4.97 out of 5 average rating, 33 reviews

Right on the bay! Heated pool! King bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed and sleeping sofa in the family room (if more than two guests coming). Full size kitchen, two family rooms, pool and gorgeous view on the salty bay for nature lovers.

Top guest favorite

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

Home in Sarasota

4.97 out of 5 average rating, 156 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

A modern living space is showcased with a comfortable dark sofa and a round coffee table on a textured area rug. A dining table with four chairs is positioned nearby, while a large window offers a view of the ocean and natural light fills the room.

Condo in Siesta Key

5 out of 5 average rating, 42 reviews

Amazing beach view! Entire unit renovated!

The entire unit is completely renovated! Brand new furniture, appliances, and 2 55-inch smart TVs, etc. It comfortably sleeps 4 people. This 1 bedroom/1 bath unit include a California king bedroom set in the bedroom, queen and full sleeper sofas in the living room, and pack-n-play for infants. Big lanai area, enjoy amazing views of the ocean. This 3rd-floor unit steps away from #1 Siesta Key beach. This unit is a short distance to siesta key village for restaurants, shops, & entertainment.

A vibrant outdoor area features a swimming pool surrounded by lounge chairs and tropical plants. A separate upper level apartment is visible, showcasing a light blue exterior. The enclosed patio area provides shaded seating, enhancing the inviting space for relaxation.

Cottage in Siesta Key

4.93 out of 5 average rating, 119 reviews

The Mermaid: Heated Pool, 4 Houses to Beach

This apartment is a first-floor unit with an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is a washer/dryer in the apartment. Beach chairs and umbrellas are supplied to you at no charge. This is a duplex and has another 1 bedroom 1 bath apartment above you.

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, 116 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!

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

4.91 out of 5 average rating, 185 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

A private heated pool is surrounded by lush tropical landscaping, featuring comfortable lounge chairs positioned on a sunlit travertine patio. The vibrant blue waters of the pool reflect the clear sky, while the inviting cottage entrance is framed by large green doors.

Home in Siesta Key

5 out of 5 average rating, 12 reviews

Toes In The Sand | Private Pool, Walk to Beach!

Exclusive Amenities Include: • Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • Outdoor Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy • Gas Grill • Enhanced cleaning protocols by our CottageClean Team • Island Shuttle Transportation Available • Dog Friendly (1 dog up to 25 lbs with an additional fee)

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, 151 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, 333 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 living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

Condo in Siesta Key

4.84 out of 5 average rating, 245 reviews

Cozy 1BR Beach Condo on Siesta Key!

Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.

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

4.97 out of 5 average rating, 334 reviews

RARE Sept SALE! OPEN! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Luxury Stays

Experience one of our premier homes

Popular amenities for Sarasota Beach vacation rentals

Free parking on premises

Air conditioning

Sarasota Beach oceanfront vacation rentals

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

4.92 out of 5 average rating, 133 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

Condo in Siesta Key

4.83 out of 5 average rating, 115 reviews

Beach Retreat - Jamaica Royale Unit #52

Top guest favorite

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

Guesthouse in Bradenton Beach

4.99 out of 5 average rating, 185 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.

Cottage in Siesta Key

4.86 out of 5 average rating, 173 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

The screened lanai offers views of palm trees and well-maintained landscaping. A small table is positioned between two chairs, and a decorative hat rests on the table. A ceiling fan hangs above, providing a cooling breeze.

Condo in Siesta Key

4.93 out of 5 average rating, 104 reviews

Siesta Key Gulf Front Condo

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

Condo in Longboat Key

4.88 out of 5 average rating, 113 reviews

Sunset and beach view from your balcony Unit 403

Top guest favorite

An oceanfront view is captured from the private lanai, showcasing the serene blue waters of the Gulf of Mexico and a heated pool below. Palm trees frame the scene, and beachgoers can be seen in the distance enjoying the sandy shore.

Condo in Longboat Key

4.98 out of 5 average rating, 202 reviews

Condo with a View 1: Open Sunday!

A spacious bedroom features a king size bed with a white bedding set and decorative pillows. Soft blue walls provide a calming backdrop. A ceiling fan is installed overhead, and natural light streams in through the window adorned with light blinds. Complementary artwork adds a touch of coastal charm.

Guesthouse in Sarasota

4.91 out of 5 average rating, 114 reviews

Super Clean Cozy and Quaint steps from the beach

Other great vacation rentals in Sarasota Beach

Top guest favorite

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.

Condo in Siesta Key

4.96 out of 5 average rating, 48 reviews

Siesta Key Beach front 2 bedroom condo w/ parking

Top guest favorite

A spacious screened-in pool area features a bright blue pool alongside lounge chairs. Strings of lights illuminate the space as the sunset casts a warm glow. Lush greenery surrounds the area, providing a tranquil setting for relaxation and entertainment.

Home in Sarasota

5 out of 5 average rating, 12 reviews

Fenced Yard|Gourmet Kitchen|Salt Water Pool|Arcade

An inviting outdoor space is showcased with a private pool surrounded by a spacious deck. Comfortable lounge chairs are positioned nearby. Soft lighting accentuates the area, with lush greenery adding a natural touch against the backdrop of the two-story home.

Home in Siesta Key

4.91 out of 5 average rating, 35 reviews

Stunning Siesta Home | 4 Bedroom | Walk to Village

Top guest favorite

The exterior of a cottage features light-colored siding and a turquoise door, framed by shade from a large oak tree. The entrance is surrounded by white gravel, with lounge chairs and beach equipment visible. Bright sunlight illuminates the scene, enhancing the tropical atmosphere.

Cottage in Siesta Key

4.95 out of 5 average rating, 86 reviews

Surf Shack- Walk to Village/Boat Dock Included

The image shows a tranquil poolside setting with lounge chairs arranged beside a heated pool. A decorative tray with candles is placed in the foreground, surrounded by smooth stones. Soft lighting from the surrounding plants creates a relaxed atmosphere as evening approaches.

Apartment in Sarasota

4.97 out of 5 average rating, 39 reviews

Modern 2/1+ shared, heated pool +4 min Siesta

A private, fenced backyard features a large heated pool with an integrated hot tub, surrounded by palm trees and lush greenery. Comfortable loungers are positioned near the pool, while a covered gazebo provides shaded seating. Sunlight highlights the tranquil atmosphere of the outdoor space.

Home in Sarasota

4.93 out of 5 average rating, 14 reviews

2b/2b house w/ a heated pool & hot tub near Siesta

The exterior of a modern home is showcased at sunset, featuring a paver driveway leading to a two-car garage. Palm trees and vibrant landscaping are present, while blue-shuttered windows complement the light-colored walls.

Home in Sarasota

4.86 out of 5 average rating, 7 reviews

Luxury Pool Home by Siesta/Lido

Top guest favorite

A well-maintained pool area is enclosed by a screened lanai, featuring a refreshing turquoise pool surrounded by a spacious patio and two lounge chairs. Direct access to the house is visible, with additional outdoor seating for relaxing or dining nearby.

Bungalow in Sarasota

4.99 out of 5 average rating, 80 reviews

*Waterfront house with dock and heated pool

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