Vacation rentals in Sarasota

4.91 out of 5 average rating, 359 reviews

A screened-in patio features a round table with decorative tile and four chairs, surrounded by lush greenery. A pool is visible in the background, reflecting the clear blue sky, providing a serene setting for relaxation and outdoor dining.

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with wood floors and lots of natural light, located in a quiet neighborhood on the downtown core edge. Enjoy a spacious and private, fenced-in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Home in Indian Beach-Sapphire Shores

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.

4.97 out of 5 average rating, 154 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.

4.99 out of 5 average rating, 190 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

A living area features wooden flooring with a large area rug at the center. Two gray armchairs are positioned near a media console, which supports a flat-screen television. Natural light is provided by windows adorned with sheer white curtains, and a green plant adds a touch of greenery.

4.95 out of 5 average rating, 504 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

4.97 out of 5 average rating, 281 reviews

A spacious bedroom features a king-size bed adorned with a blue and white textured coverlet. Soft natural light filters through the window, illuminating the room, which includes a nightstand, dresser, and a comfortable bench at the foot of the bed.

Guesthouse in Sarasota

Sarasota guest house only 8 miles to Siesta Key

Our Florida-themed guest house has everything you need to enjoy your vacation in beautiful Sarasota, Florida. It is a very comfortable, clean and private one bedroom and one bathroom guest house. It is a completely separate space and has it's own private entrance. It is conveniently located in a quiet, safe neighborhood near Interstate I-75, Shopping, Dining, Twin Lakes Park, Serenoa Golf Course, Myakka River State Park and just 8 miles from the #1 beach in the U.S. - Siesta Key Beach.

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 156 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.94 out of 5 average rating, 162 reviews

Newly Renovated Ranch Minutes From Beach/Downtown

Newly renovated cozy home with all new furnishings and appliances. 2 bedrooms 1 bathroom with an eat in kitchen, sun room, and comfy living room. Stream shows or work virtually with our high speed WIFI. Grab the beach chairs and umbrella to enjoy Lido Key or Siesta Key Beaches both within a short drive. Wind down & grab drinks/dinner in downtown Sarasota or relax in the backyard. Several golf courses near-by or catch Orioles spring training at Ed Smith stadium within walking distance.

4.93 out of 5 average rating, 229 reviews

A modern guest room features a spacious bed adorned with patterned bedding. A red accent chair is positioned nearby, complementing the decor. Light is provided by ceiling fixtures, and a piece of floral artwork is displayed on the wall. Simple furnishings include a small table and wastebasket.

Guest suite in Sarasota

MG Tropical Stay.With private entrance and patio.

Welcome to your modern Guest Suite in Sarasota – Adults Only, Private & Peaceful 🌞 Enjoy your own private space—no shared areas—with a separate entrance and parking for two cars. The suite includes: A cozy queen bed A full bathroom A well-equipped kitchenette with a microwave, small refrigerator, coffee maker, and 2-burner cooktop A secluded outdoor patio with a solar shower, ideal for rinsing off after a beach day A mini-split A/C unit to keep you cool during Florida’s sunny days

The front exterior of the home features a light grey facade with stone accents. Two comfortable chairs are positioned on the covered porch, inviting relaxation. A brick driveway with ample space leads up to the entrance, surrounded by landscaped areas and a peaceful neighborhood view.

4.93 out of 5 average rating, 194 reviews

Sea-esta Cottage- Cheerful 2bd/1ba w/ free parking

Experience ultimate relaxation in this serene and stylish rental. A brand-new home in the heart of Amish Village, Pinecraft. Two cozy bedrooms with plush bedding and soothing coastal decor. Sip your coffee on the front porch, immersed in the tranquility of this idyllic neighborhood. Take a short walk to Yoder's Restaurant, Coastal 98 Cafe, and the Pinecraft Ice Cream Shop. Just 6 miles to Siesta Key and 7 miles to Lido Beach for endless coastal adventures.

Home in Indian Beach-Sapphire Shores

A rustic wooden sign with the word 'Welcome' painted in white is displayed prominently. Dried floral arrangements are arranged above the sign, adding a natural touch. A small turquoise glass jar sits nearby, contributing to a warm and inviting entryway.

4.9 out of 5 average rating, 680 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

4.99 out of 5 average rating, 141 reviews

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

Guesthouse in Sarasota

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

The open-concept living space features a comfortable sectional sofa, a wooden coffee table, and an accent chair, complemented by a large American flag artwork. The kitchen area showcases modern cabinetry, a large island with seating, and ample lighting for a welcoming environment.

4.98 out of 5 average rating, 157 reviews

Secluded Cottage | Hot Tub | Walk to Benderson/UTC

Welcome to The Crew House! A brand new, stylish, cozy cottage that is walking distance to all that the Nathan Benderson Park and University Town Center areas have to offer! The property is on over a 2 acre parcel so there's plenty of room to spread out. At our cottage you will find a comfortable bed, stylish furniture, high-end finishes, a large island, screened-in outdoor dining table, and a great outdoor space with a private hot tub.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Sarasota vacation rentals

Self check-in

Beachfront

Pet friendly

Laptop-friendly workspace

Gym

Sarasota beach vacation rentals

4.96 out of 5 average rating, 119 reviews

A two-story building is shown, featuring a wraparound porch adorned with railings and chairs. Lush green foliage leads to a sandy path, inviting access to the beach. The sky is partly cloudy, enhancing the coastal ambiance of the location.

Condo in Englewood

Sunset Beach

4.84 out of 5 average rating, 244 reviews

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

Cozy 1BR Beach Condo on Siesta Key!

4.97 out of 5 average rating, 331 reviews

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

On the Beach; Siesta Key SunBum Studio

Apartment in Longboat Key

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.

4.95 out of 5 average rating, 108 reviews

Longboat Key-OCEAN FRONT- on the beach

4.99 out of 5 average rating, 144 reviews

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.

Condo in Bradenton Beach

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

4.91 out of 5 average rating, 274 reviews

A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.

Guesthouse in Englewood

Gulf front romantic cottage in paradise

4.98 out of 5 average rating, 196 reviews

A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.

Condo in Longboat Key

Condo with View 1: Open Sun-Wed, $194/nt + Fees!

4.99 out of 5 average rating, 195 reviews

Lounge chairs with blue and white striped canopies are positioned on the sandy beach, offering shade and comfort. The expansive shoreline stretches into the distance, meeting a calm, turquoise sea under a partly cloudy sky.

Apartment in Siesta Key

Siesta Key #1 Beach, pickle ball & tennis paradise

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Pet-friendly vacation rentals in Sarasota

Home in Indian Beach-Sapphire Shores

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.96 out of 5 average rating, 93 reviews

Retreat by the Bay-Heated Saltwater Pool

4.92 out of 5 average rating, 24 reviews

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.85 out of 5 average rating, 101 reviews

Charming Villa 14 mins away from Siesta Key Beach

4.93 out of 5 average rating, 167 reviews

An outdoor space features a heated pool surrounded by gray paving stones. A black pergola with string lights provides shade over a swing couch positioned next to a fire feature. Lounge chairs are arranged nearby, with a small table holding drinks. Lush greenery is visible in the backdrop.

Home in Bradenton

Chic Oasis-Backyard Goals-Game Room-Pup Haven-Pool

A private pool is surrounded by a spacious patio with paver stones, offering an inviting area for relaxation. Several lounge chairs and a small table with decorative seating are positioned near the water. Lush greenery borders the yard, enhancing the secluded feel.

4.77 out of 5 average rating, 109 reviews

Pool house by the bay

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.93 out of 5 average rating, 100 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

An inviting living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.

4.96 out of 5 average rating, 129 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

An outdoor dining area features a large table set with plates and glasses, surrounded by seating. A pool is visible nearby, framed by lounge chairs under a covered patio with ceiling fans. The walls are painted in a vibrant blue, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 174 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

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Sarasota home rentals

4.88 out of 5 average rating, 43 reviews

A serene outdoor seating area features two adirondack chairs in vibrant orange and blue, positioned beside a small green table. The tranquil lake reflects the soft light of a sunset, surrounded by lush tropical vegetation and a peaceful atmosphere.

Home in Englewood

Suite Sun

An inviting outdoor space features a private in-ground saltwater pool, surrounded by green grass and lounge chairs. Tropical landscaping provides a serene backdrop, with various plants and trees enhancing the atmosphere. Two umbrellas and a shaded seating area facilitate relaxation and outdoor enjoyment.

4.75 out of 5 average rating, 4 reviews

Artsy 3BR/2BA Pool Home Arlington Park

An expansive outdoor space features a heated pool and an 8x8 spa, surrounded by a stone patio. Lounge chairs and a patio dining set are arranged invitingly. The sky is painted with soft hues of orange and pink as twilight descends.

5 out of 5 average rating, 46 reviews

Sarasota Memories For a Lifetime

An expansive outdoor area surrounds a sparkling pool, framed by lush grass and swaying palms. Comfortable loungers are positioned beside the pool on newly laid pavers. A serene backdrop features the home's exterior with large windows, under a clear blue sky accented by fluffy white clouds.

5 out of 5 average rating, 9 reviews

Tropical Oasis | Fully Remodeled | Private Pool

The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.

4.89 out of 5 average rating, 84 reviews

Gorgeous renovation with pool, minutes from beach

5 out of 5 average rating, 5 reviews

A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.

Home in Rotonda West

Turtle Bay - minutes to Boca Grande!

4.92 out of 5 average rating, 24 reviews

An aerial view captures a light blue house with a spacious driveway and manicured lawn, surrounded by lush greenery and a serene canal. The home features a charming front porch and is set within a quiet neighborhood, showcasing the tranquil natural landscape.

Home in Port Charlotte

Peaceful waterfront home

A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.