House holiday rentals in South Sarasota

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.

4.99 out of 5 average rating, 122 reviews

Siesta Breeze ~ Charming Coastal Cottage

Message me for 🔥🔥 last minute deals!! 5 miles from Siesta Beach, named No 1 Beach in the US, No 4 in the World by Tripadvisor; close enough to feel the sea breeze:) You will have 2 bathrooms, 2 bedrooms with queen beds and a flex room with a futon and work area, for 3 private sleeping areas. You will be located in the heart of Sarasota, with restaurants and grocers within a mile or two. The kitchen is fully equipped and the yard fully fenced. The host is conveniently located next door.

5 out of 5 average rating, 13 reviews

"Siesta on Lee" - NEW SRQ Home w/ Heated Pool!

Unwind in this charming Sarasota retreat! This 3 bed/2 bath home is just a 10-minute drive from both downtown SRQ and stunning Siesta Key, making it an ideal location. This property features 3 queen beds and 1 bunk bed, perfect for families or groups. With 2 full bathrooms, a fully equipped kitchen, cozy living room, game room, and private pool (option to HEAT) with loungers, the home comfortably hosts up to 8 guests. You've found the perfect place to call home while you're away from yours!

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.

4.98 out of 5 average rating, 137 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

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.

4.98 out of 5 average rating, 204 reviews

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!

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 122 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

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.

4.87 out of 5 average rating, 136 reviews

Charming Villa 14 mins away from Siesta Key Beach

This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property comes fully equipped with amenities such as a BBQ, outdoor umbrella, lounge chairs, beach chairs, pickleball rackets, washer/dryer and carport. Featuring 2 bedrooms, this charming home exudes a warm vibe. You can reach Siesta Key Beach, St. Armands Circle, and Downtown Sarasota in under 15 minutes, making it easy to explore all that Sarasota has to offer during your stay.

A distinctive triangular structure features large glass windows, showcasing vibrant lighting from within. The exterior is surrounded by landscaped greenery and decorative white stones, enhancing the inviting appearance. Palm trees and a tidy paved driveway contribute to the overall charm and unique architectural design.

4.95 out of 5 average rating, 242 reviews

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

A vibrant blue exterior of the home is highlighted by white trim and large windows. The entrance features a wooden deck with a small step, while surrounding landscaping includes gravel and small plants. Mature trees provide shade in the front yard.

4.93 out of 5 average rating, 140 reviews

Papi's House - 5 miles to Siesta Key & Downtown

This newly remodeled 2 bed, 2 bath home is centrally located in Sarasota. With plenty of space to spread out, beautiful natural light that pours into every room and a private fenced-in yard, this is the perfect place to relax. This home is located in a quiet neighborhood and just 5 miles away from the #1 rated Siesta Key Beach and downtown Sarasota. It offers plenty of driveway parking. Beach chairs and a cooler are provided for your days at the beach. Fast WIFI is also available.

4.95 out of 5 average rating, 193 reviews

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. VR24-00265

A private backyard features a heated in-ground pool surrounded by spacious pavers. Lounge chairs are positioned along one side, with a shaded table and umbrella nearby. Lush greenery lines the perimeter, providing a natural backdrop for relaxation and leisure.

4.91 out of 5 average rating, 22 reviews

The Pink Pineapple - Your Cozy Sarasota Home

Welcome to The Pink Pineapple, your cozy Sarasota retreat! Just 10 minutes from Siesta Key Beach, this charming home offers a bright, tropical vibe with all the comforts you need. Enjoy a fully equipped kitchen, spacious living areas, dedicated laundry room and a private backyard perfect for relaxing and hanging in the heated saltwater pool. Close to downtown, dining, and shopping, it's the ideal spot for a beach getaway or exploring Sarasota's arts and culture.

The exterior of a midcentury waterfront home is showcased, featuring a smooth driveway leading to a modern facade accented with orange and white. Lush greenery surrounds the property, including palm trees and manicured lawn areas, under a bright sky with scattered clouds.

4.94 out of 5 average rating, 86 reviews

Waterfront Home by Ralph Twitchell

Beautiful midcentury waterfront home on Phillipi Creek close to all that Sarasota has to offer. 5 miles to America's number 1 beach Siesta Key, and only a few short blocks from stores, nightlife, & other beaches. This quaint getaway includes a kayak to enjoy the pure bliss of the calm waters of Phillipi Creek as well as a game room including a pool table, foosball table, and a fireplace to lounge around and chat.

4.98 out of 5 average rating, 116 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

Popular amenities for South Sarasota house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 157 reviews

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

4.98 out of 5 average rating, 113 reviews

Pool, Shuffleboard, EV charg, Near beach, UTC mall

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.

4.94 out of 5 average rating, 158 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

4.97 out of 5 average rating, 33 reviews

Downtown Tropical Getaway w/ heated pool

A spacious outdoor dining area features a large table surrounded by six chairs, positioned on a light blue surface. In the background, a crystal clear pool reflects sunlight, while an umbrella provides shade. A fenced perimeter and greenery enhance the setting's privacy.

4.93 out of 5 average rating, 141 reviews

Centrally located oasis.

4.86 out of 5 average rating, 114 reviews

Roselawn St | Private Pool, Fire Pit + Patio!

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.

4.95 out of 5 average rating, 133 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

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.

4.93 out of 5 average rating, 90 reviews

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Weekly house rentals

4.97 out of 5 average rating, 33 reviews

Home in Arlington Park

Modern Home Heated Pool near Siesta & Downtown

An open living area features a light-colored seating arrangement, including two armchairs and a sofa, with a wooden coffee table at the center. A wall-mounted TV is visible, and a dining area with a table and chairs is located nearby. Natural light enters through sliding glass doors.

5 out of 5 average rating, 43 reviews

Cozy Getaway Home near Siesta Key Beach

Superhost

A crystal-clear swimming pool is surrounded by lush tropical vegetation. The gently curving pool shape complements the inviting aqua water, while a concrete deck provides ample space for relaxation. Bright blue sky with fluffy clouds can be seen overhead, enhancing the outdoor atmosphere.

Home in Gulf Gate Estates

4.64 out of 5 average rating, 14 reviews

Sarasota Dreaming!

5 out of 5 average rating, 29 reviews

Near Siesta Key | Palm-Lit Nights, Pool & Spa

4.79 out of 5 average rating, 19 reviews

The Siesta Key Pool House – Private Inland Oasis

A spacious outdoor area is visible, featuring a hammock strung between supports under a screened canopy. The refreshing pool can be seen in the background, with large glass doors leading into the interior of the home. Lush greenery surrounds the pool area.

4.96 out of 5 average rating, 25 reviews

Enchanted & peaceful Oasis 10 min from the Beach

Home in Gulf Gate Estates

The exterior of a charming cottage is framed by a white fence and lush greenery. A welcoming archway leads to a porch adorned with large windows, offering glimpses of the intricate woodwork and vibrant flowering plants that enhance the entrance.

4.96 out of 5 average rating, 49 reviews

The Ashton Retreat

5 out of 5 average rating, 20 reviews

Coastal Getaway minutes from Siesta Key Beach

Private house rentals

4.82 out of 5 average rating, 17 reviews

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

Home in Arlington Park

Sarasota's Luxury Oasis

A spacious bedroom features a light-colored bed adorned with neutral bedding. A cozy chair is positioned nearby, complemented by a decorative area rug. Natural light streams through large windows, and a brick wall hosts a television above a decorative fireplace.

5 out of 5 average rating, 30 reviews

Little Creek Retreat/4.5 mi to the Beach!

4.97 out of 5 average rating, 36 reviews

Spacious Sarasota family home Mins from the beach

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.

5 out of 5 average rating, 32 reviews

The Palms Away

A stylish living area features a round wooden table surrounded by two light-toned chairs. The space is complemented by a modern kitchen with bar seating and pendant lighting. Light-colored walls and soft lighting contribute to a calm atmosphere, with a piece of wall art adding a decorative touch.

4.94 out of 5 average rating, 34 reviews

Experience "Old Florida" at the Coral Cottage

A swim spa is illuminated by soft, colorful lighting, offering a tranquil setting for relaxation. Surrounding the spa, a landscaped area features stepping stones and decorative pebbles, with tropical plants and trees creating a serene atmosphere. Ambient lighting along the path enhances the outdoor space.

4.92 out of 5 average rating, 63 reviews

SARASOTA PLACE NEAR SIESTA BEACH

A spacious living area features a comfortable light-colored sofa complemented by a vibrant blue accent chair. The floor showcases a bold black-and-white rug, while artwork adorns the walls. A side table with a lamp is visible, creating an inviting atmosphere for relaxation.

4.92 out of 5 average rating, 89 reviews

Ben's Bungalow | 8 min to Siesta Key | Gigabit Wifi

A fenced backyard showcases a heated pool surrounded by landscaped areas. Lounge chairs are positioned beside the pool, inviting relaxation. Sunlight reflects off the water, while a screened lanai provides a shaded space for enjoyment.