Family-friendly holiday rentals in South Sarasota

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, 73 reviews

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

Ben's Bungalow is all about comfort and convenience. Just 3 miles and an 8 minute drive from Siesta Key Beach, it's the perfect home-base for your next Sarasota adventure and promises an unforgettable retreat for you and your crew. The large 3rd bedroom boasts an ultra-comfortable Nectar mattress and a 65” curved screen HDTV. Enjoy the Gigabit Wi-Fi, and the back-yard comes pre-stocked with fresh firewood, marshmallow sticks, and a privacy fence ready for you to make great memories with the fam.

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.

4.93 out of 5 average rating, 147 reviews

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want! Please message me if bringing 2+ pets

4.83 out of 5 average rating, 177 reviews

Siesta Beach, 5 minutes from downtown.

My place is close to art and culture, restaurants and dining, great views, the Siesta Beach, Turtle Beach, and family-friendly activities. You’ll love my place because of the neighborhood, the comfy bed, the kitchen, and the coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids). Its located right next to the north bridge to Siesta Beach North Bridge Outlook Park, you can walk to the water. Certificate Number – The certificate number [VR24-00082]

Guest house in South Sarasota

A spacious sleeping area features a comfortable bed with white bedding, accompanied by a leather couch. A mounted television is positioned on the wall, and decorative plants add a touch of nature. A side table with a lamp complements the warm decor.

4.96 out of 5 average rating, 79 reviews

The Getaway

Relax in this comfortable and stylish space only 2 miles from Siesta Beach. The Getaway is the perfect spot to relax whether you're here on business or you've spent the whole day on the beach. The space is newly remodeled and you will lack nothing here! Enjoy the outdoor deck and two Nigerian Dwarf goats that live on the property. The Getaway is an apartment style space attached to the main home. It has it's own entrance and is completely private. The host lives in the main part of the home.

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.

4.99 out of 5 average rating, 122 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.

4.97 out of 5 average rating, 184 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!

An inviting private backyard features a sparkling heated pool surrounded by a spacious screened patio. Comfortable loungers are positioned nearby, with a shady area provided by the overhead structure. Lush greenery accents the space, enhancing the tranquil outdoor atmosphere.

4.89 out of 5 average rating, 103 reviews

Siesta Key FL: Heated Pool, Beaches, Family Fun

Escape to a stylish and spacious retreat near the world-famous Siesta Key Beach! This 3-bedroom, 2-bathroom home sleeps up to 10 guests, making it perfect for families, groups, or workcations. Relax by the private heated pool in the fenced backyard, whip up gourmet meals in the fully equipped kitchen, or explore Sarasota’s vibrant dining, shopping, and cultural attractions just minutes away. Whether you’re here to soak up the sun or create family memories, your Florida getaway starts here.

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, 116 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!

4.97 out of 5 average rating, 264 reviews

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

4.86 out of 5 average rating, 106 reviews

Roselawn St | Private Pool, Fire Pit + Patio!

BNB Breeze Presents: Roselawn Street! Located in the heart of Sarasota, just 10 minutes away from Siesta Key Beach, the location of this home is everything! This stunning oasis with a private pool and basketball court includes: • Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Miniature Basketball Court • Covered Outdoor Dining Area + Grill • Lightning Fast Wi-Fi (Perfect for Remote Work!) • Incredible Fire Pit w/ String Lights! • 2 Living Rooms

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.

4.94 out of 5 average rating, 117 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.98 out of 5 average rating, 151 reviews

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

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

Popular amenities for South Sarasota family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A private backyard is illuminated with string lights in the evening. A fire pit table with a glass barrier features dancing flames, while a hammock is visible to the side. The space includes lounge seating with turquoise cushions, creating a relaxed outdoor atmosphere.

4.91 out of 5 average rating, 170 reviews

Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower

The backyard features a newly constructed pool accompanied by a hot tub, both surrounded by vibrant greenery and tropical landscaping. A sun shelf is present in the pool, while a patio area with seating is visible in the background under the shade of trees.

4.98 out of 5 average rating, 101 reviews

Sun-filled cottage with pool, walk to beach

The outdoor area features a heated pool surrounded by a serene landscape of palm trees and decorative stones. An adjacent BBQ grill offers outdoor cooking options, while comfortable seating is available nearby. The patio area is partially shaded by a pergola, providing a relaxing space.

4.96 out of 5 average rating, 224 reviews

The Oasis-Heated Private Pool Hot Tub-5mi to beach

4.96 out of 5 average rating, 105 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

4.97 out of 5 average rating, 351 reviews

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

JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 120 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

4.92 out of 5 average rating, 130 reviews

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

Home in Saint Armands

St Armand's Mid-Century Oasis

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.

4.98 out of 5 average rating, 127 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

Family- and pet-friendly home rentals

Superhost

The living area features a light-colored sofa complemented by an orange accent chair. A coffee table sits on a textured area rug, while wall art adds color to the red accent wall. Glass doors open to a view of outdoors, surrounded by greenery.

Apartment in Gulf Gate Estates

4.91 out of 5 average rating, 138 reviews

Sunny 2nd-Floor Condo w/ Heated Pool | 1BR

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.

4.88 out of 5 average rating, 123 reviews

Charming Villa 14 mins away from Siesta Key Beach

A screened-in pool area features a crystal-clear heated pool with lounge chairs positioned nearby. An umbrella provides shade over a seating area, surrounded by lush greenery and fencing that enhances privacy.

4.95 out of 5 average rating, 232 reviews

Cozy 2BD/2BA with Heated Pool Near Siesta Key

Apartment in Gulf Gate Estates

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.

4.97 out of 5 average rating, 125 reviews

Modern Studio · 5 min from Siesta Beach

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.

4.95 out of 5 average rating, 266 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

4.91 out of 5 average rating, 183 reviews

Guest suite in Sarasota

Sweet, pet friendly Siesta Suite

Superhost

A serene pool area is surrounded by lush greenery and wooden fencing. Aquamarine water reflects sunlight, while a few poolside lounge chairs in turquoise invite relaxation. Potted plants add a touch of color, and a floating pool accessory rests on the surface.

4.93 out of 5 average rating, 120 reviews

5Stars Tiki, Heated Pool, Close to Beaches and ALL

4.87 out of 5 average rating, 421 reviews

A spacious room features a king size bed with coordinating pillows and light bedding. A chic chandelier hangs from the ceiling, illuminating the space. Natural light enters through the window, while a comfortable seating area with decorative pillows and a coffee table complete the inviting environment.

Guest house in Sarasota

The Cottage, very close to Siesta Beach!

Family-friendly home rentals with a pool

5 out of 5 average rating, 9 reviews

Sarasota Refuge & Pool Oasis

5 out of 5 average rating, 11 reviews

An outdoor dining area is presented next to a heated pool, featuring a table set with plates of food and drinks. A gas grill is nearby, and the pool is enclosed by a mesh screen. Lush greenery is visible through the enclosure, enhancing the serene environment.

Home in Arlington Park

Paradise on Prospect w/ Htd Saltwater Pool

4.91 out of 5 average rating, 23 reviews

Home in Siesta Key

Coastal Luxury*Pool*Hot Tub*Sunsets*Close to 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, 19 reviews

The Palms Away

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.96 out of 5 average rating, 153 reviews

Beautifully Remodeled Home with Pool Near Siesta

A serene outdoor space features a refreshing pool with clear water surrounded by a sunlit patio. Lush green grass borders the pool area, while tropical plants add a natural touch. A neutral-toned wall serves as a backdrop, enhancing the peaceful atmosphere.

5 out of 5 average rating, 15 reviews

House minutes to Siesta

A spacious outdoor seating area features comfortable rattan furniture arranged around a round table. Soft cushions and patterned throws add a cozy touch, while sheer curtains gently sway. A backdrop of lush greenery enhances the tranquil atmosphere of this inviting space.

4.95 out of 5 average rating, 21 reviews

House of Peace oasis,heated pool, pool table, fire

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.