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, 128 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.

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, 142 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, 209 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!

4.95 out of 5 average rating, 195 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. *Brand new pool* VR24-00265

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, 123 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!

A modern bedroom features a spacious bed adorned with light, textured bedding and accent pillows. Above the bed, three abstract paintings in muted tones are displayed. A small, vibrant flower sits in a minimalist nook attached to the white headboard.

4.96 out of 5 average rating, 138 reviews

Modern Family Oasis Near DT Sarasota & Beaches

A tranquil and spacious 3BR/2BA house awaits you on a serene, traffic-free street. This luxurious abode boasts high-beamed ceilings and inviting details, creating an atmosphere that is both comfortable and refined. With its location just 7 miles from Siesta Key Beach, 6 miles from Lido Beach, and 2.5 miles from Downtown, this property offers convenience and accessibility. Enjoy your coffee on the lanai as you plan your day. (City of Sarasota Vacation Rental Certificate # VR25-00125)

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, 141 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.

5 out of 5 average rating, 7 reviews

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

4.95 out of 5 average rating, 109 reviews

A single-story home is showcased with a light exterior and grey roof. Blue shutters adorn the windows, while lush greenery and colorful landscaping enhance the front yard. A screened wraparound porch offers additional outdoor space. The property is bordered by a paved walkway.

Home in Arlington Park

Sarasota 2B/2B Near Siesta Key/Arlington Park/SMH

This newly renovated property is equipped with 2 bedrooms and 2 full bathrooms, full kitchen with all appliances, washer/dryer, screened wraparound patio, and fenced-in yard. Safe and beautiful walking neighborhood - 15 minute walk to Arlington Park and Recreation Center. 7 minute walk to Sarasota Memorial Hospital and Southside Village restaurants & shops. 15 minute drive to Bayfront Park, Selby Botanical Gardens, Marina Jack, St. Armand's/Lido Key and Siesta Key Beach.

4.88 out of 5 average rating, 8 reviews

Luxe Modern Home - Private, Friendly & Stylish

Welcome to Lux Modern Home, a stylish modern home just minutes from the world-famous Siesta Key Beach. Thoughtfully designed with clean lines, coastal tones, and smart features, this 1,400 sq ft retreat offers the perfect balance of comfort, privacy, and contemporary living. Whether you’re here for beach days, sunset walks, or a relaxing getaway, this home is an ideal base for couples, families, or friends seeking a calm and upscale coastal experience.

The exterior of a charming adobe-style home is highlighted, featuring a light blue facade and a decorative entrance. A pathway leads to the door, bordered by colorful plantings and a white picket fence. Tropical plants add to the serene ambiance of the front garden.

4.95 out of 5 average rating, 116 reviews

Casa de Zara| Downtown Sarasota- 5mi Lido Beach

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!

4.98 out of 5 average rating, 121 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

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, 162 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

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.

4.92 out of 5 average rating, 143 reviews

Centrally located oasis.

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, 134 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

4.95 out of 5 average rating, 41 reviews

Home in Arlington Park

Modern Home Heated Pool near Siesta & Downtown

4.93 out of 5 average rating, 400 reviews

Heated&Renovated Pool•Beach Retreat•15m to Siesta

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 130 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

5 out of 5 average rating, 16 reviews

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

The outdoor area features a well-maintained pool bordered by lush greenery. Several loungers and a shaded seating area invite relaxation. A vibrant red umbrella provides sun protection, while the sky above showcases a mix of clouds and blue, enhancing the serene atmosphere.

4.85 out of 5 average rating, 20 reviews

Siesta Shore House

Weekly house rentals

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, 36 reviews

The Palms Away

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, 23 reviews

The Pink Pineapple - Your Cozy Sarasota Home

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.

4.95 out of 5 average rating, 38 reviews

Experience "Old Florida" at the Coral Cottage

A spacious living area is furnished with comfortable grey sofas and a central coffee table. A wall-mounted television displays scenic Florida imagery. Natural light filters through sheer curtains covering large windows, enhancing the overall bright atmosphere. The open layout connects to the dining area and kitchen.

4.82 out of 5 average rating, 73 reviews

Siesta Getaway-Minutes to 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, 91 reviews

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

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

5 out of 5 average rating, 6 reviews

Sapphire Shores Muse | 2 Bed 3 Bath | Luxe Pool

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, 52 reviews

The Ashton Retreat

Private house rentals

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, 31 reviews

Little Creek Retreat/4.5 mi to the Beach!

Superhost

4.82 out of 5 average rating, 22 reviews

Endless Summer | Private Pool & HOT TUB

4.95 out of 5 average rating, 37 reviews

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

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.

5 out of 5 average rating, 52 reviews

Waterfront Retreat | Heated Pool & Boat Dock

A screened-in outdoor seating area is featured, furnished with a large sectional sofa adorned with red accent pillows. A low coffee table holds a bowl of fresh fruit and drinks, overlooking a sparkling pool surrounded by lush greenery.

4.98 out of 5 average rating, 99 reviews

Modern Pool House Sealand 3/2 near Siesta

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.

4.91 out of 5 average rating, 65 reviews

SARASOTA PLACE NEAR SIESTA BEACH

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, 96 reviews

Gorgeous renovation with pool, minutes from beach

A modern one-story home is framed by lush landscaping and mature trees. The façade features a sleek, dark exterior with large windows and a symmetrical entrance. A paved driveway leads up to the two-car garage, enhancing the welcoming curb appeal.