Family-friendly holiday rentals in Sarasota

4.99 out of 5 average rating, 203 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 private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.

4.99 out of 5 average rating, 243 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

4.88 out of 5 average rating, 161 reviews

A cozy interior space features a daybed with a patterned cover and a wooden loft ladder leading to the sleeping area. Natural light filters through the windows, illuminating the wood accents and the kitchenette area with appliances visible in the background.

Farm stay in Arcadia

A lil country, A lil beach time

* Enjoy the lovely setting of this romantic spot in nature, a full acre with a small pond! Only 45 minutes to most beaches. Beautiful country with small antique town and parks to explore. Private acre close to farm. Walk out the door and see farm animals and a lovely pond. 2 loft bedrooms with queen beds. Downstairs has a daybed. Kitchenette complete with fridge sink and cook stove. Outside bar area on one side and the other has a fire pit and hammock. So the WiFi iffy. . plenty of DVD’s!

A well-appointed bedroom features a spacious bed with decorative pillows. Soft natural light filters through the window, which is adorned with brown and beige curtains. A vintage mirror adds an elegant touch, while a bedside table with a lamp provides functional lighting.

4.92 out of 5 average rating, 197 reviews

Cozy Guesthouse in central Sarasota!

This cozy independent guesthouse is perfect for all ocations from a few business day stay to a vacacion getaway. Near to siesta key beach! Enjoy a private room with a comfortable bed, a bathroom with a great shower and hot water, plus a cozy bar-style area perfect for preparing snacks and coffee. You’ll also have access to a small patio where you can unwind, and we provide beach essentials. Perfect for travelers seeking comfort and peace, and a well-equipped space. We’d love to host you!

Guest suite in Downtown Sarasota

A colorful room features a green bed frame with a patterned comforter, complemented by a dark desk and a matching chair. A small black television is positioned on the desk, while a glass table adds an additional functional space. The walls are painted a warm yellow.

4.92 out of 5 average rating, 445 reviews

SUPER CLEAN 100% Private Downtown Location

A very private, quiet and secure space with a new comfortable Queen size bed, best of linens, 100% private attached bathroom and shower. Walk to downtown, waterfront and Payne Park. Complimentary bicycles, beach cooler, beach towels and umbrella! 100 Meg WiFi, large desk, LED TV. Delightful husband/wife "Superhosts" tend to your every need including complimentary bottled water, Starbucks coffee and Bigelow tea. We utilize the Airbnb and State of Florida anti-bacterial cleaning protocols.

A spacious studio features a comfortable king-sized bed with decorative pillows and a cozy leather couch. A mounted TV is visible alongside a desk area, while a kitchenette is seen in the background. Warm light enhances the inviting layout, complemented by modern decor.

4.93 out of 5 average rating, 507 reviews

Clean and Modern Sarasota Studio

Our studio is private, comfortable, stylish, & efficient. Whether you are coming for business or leisure, we are sure you will have everything you need. Our home is newer (built in 2020) and we designed this space specifically with Airbnb guests in mind. Our neighborhood is central to almost all of Sarasota! We were born and raised here, and in our opinion this area is central to everything! Whether you are headed to Siesta, Myakka State Park, or UTC mall, you won't be driving for long!

The studio apartment features a spacious bed with light-colored linens, complemented by two decorative pillows. A sleek brown sofa is positioned in front, adorned with a soft throw blanket. Natural light enters through the window, enhancing the clean and modern design.

4.82 out of 5 average rating, 201 reviews

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

4.93 out of 5 average rating, 249 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. Fully private, no shared spaces

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

4.99 out of 5 average rating, 331 reviews

A pathway made of stone leads to a light green structure nestled among lush foliage. Tropical plants and vibrant red flowers surround the pathway, creating a serene outdoor setting under a clear blue sky. The area is shaded by tall trees, enhancing the peaceful ambiance.

Tiny home in Sarasota

Unique tropical stay - 5 minutes to Siesta Key

Welcome to “The Stream” — a hidden tropical retreat tucked away in the heart of Sarasota. This one-of-a-kind space offers the perfect blend of seclusion and convenience. Just 5 miles from the world-famous Siesta Key Beach and 3 miles from downtown Sarasota. Stroll or bike to nearby cafés, acclaimed restaurants, boutique salons, Publix, Trader Joe’s, CineBistro, and more. Whether you’re here to unwind or explore, “The Stream” is your private paradise.

4.93 out of 5 average rating, 146 reviews

A cozy sleeping area is highlighted by a framed beach scene above a bed adorned with green and white patterned pillows. A white tray holds two glasses and a small potted plant, positioned on a white quilt. Light wood paneling accents the walls.

Tiny home in Bradenton

Cozy, relaxing studio 17 minutes from the beach.

This is a (small) space in my home (162 square feet), renovated, cozy and beautiful, Fully equipped so you can enjoy a pleasant and comfortable stay. Totally private and independent. Located in a very quiet and safe neighborhood, just 17 minutes from Anna Maria and other beautiful beaches, nature reserves and other attractions. ready for 1 or 2 people.( We have another beautiful stay for 2 people on the same property).

Apartment in Arlington Park

A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.

4.98 out of 5 average rating, 179 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

A shared pool area is enclosed with a screened structure, featuring a clear blue pool surrounded by greenery. Two lounge chairs with decorative cushions are positioned near the water, inviting relaxation in a serene outdoor space.

4.95 out of 5 average rating, 312 reviews

The Lovely Stay |6 miles to Siesta Key Paradise

Relax and recharge in this bright, cozy guest house just minutes from Sarasota’s top beaches, dining, and shops. Features: • Queen bed with soft linens • Kitchenette with essentials • Full private bathroom toiletries & fresh towels • Private entrance (100 ft from main house) • Quiet neighborhood • Shared pool access Perfect for a beach getaway or business trip!

Popular amenities for Sarasota family-friendly rentals

Kitchen

Wi-Fi

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, 158 reviews

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

An inviting pool area is framed by a protective screen, with soft lighting illuminating the space. Lush plants hang from the ceiling, and a decorative piece is positioned on the wall, creating an atmosphere of relaxation and calmness.

4.9 out of 5 average rating, 100 reviews

Cabana/Guest house w/spa/pool 5min to Siesta key.

4.97 out of 5 average rating, 342 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

*DEC SALE! Sarasota #1 Luxury Villa w/PRIV BEACH!

4.97 out of 5 average rating, 118 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.93 out of 5 average rating, 119 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

4.98 out of 5 average rating, 119 reviews

A comfortable living area features a sectional sofa and a coffee table on a patterned rug. A large flat-screen television is mounted on a wood-accented wall. Natural light filters through sheer curtains, and a decorative plant adds a touch of greenery to the space.

Home in Bradenton

Beach House with jacuzzi near AnnaMariaIsland

4.78 out of 5 average rating, 361 reviews

A cozy living area is highlighted by a navy blue sofa adorned with decorative pillows. A colorful piece of wall art draws attention, while two pendant lights cast a warm glow. A small white table holds a yellow lamp, and a potted plant adds a touch of greenery.

Bungalow in Osprey

Osprey,Buttonwood Cottage.Hot tub -patio.Sublime !

A private outdoor space is presented, featuring a heated saltwater pool illuminated by soft lighting. A hammock is hung nearby under a stylish frame, surrounded by lush greenery and a fenced area, enhancing the serene ambiance for relaxation.

4.96 out of 5 average rating, 114 reviews

The Wisteria Oasis W/swings, heated pool & hot tub

Family- and pet-friendly home rentals

An inviting outdoor space features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned along the poolside, with lush greenery and tropical plants enhancing the landscape. A pergola provides shaded seating, creating a comfortable area for relaxation and entertainment.

4.93 out of 5 average rating, 105 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

A welcoming living space is visible through an opening, featuring a comfortable blue chair and a wall-mounted TV. Natural light filters through a window, illuminating the white walls and partially covering a cozy bed with blue and white bedding in the adjacent area.

4.88 out of 5 average rating, 232 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

4.83 out of 5 average rating, 119 reviews

A newly remodeled studio features a kitchenette with white cabinets and a small microwave. Two dark wood chairs are positioned around a circular table, and a small refrigerator is visible on the floor. A wall-mounted air conditioning unit is installed above the kitchenette.

Guest suite in Bradenton

Cozy Studio in Quiet Neighborhood

4.77 out of 5 average rating, 150 reviews

A newly constructed cottage is showcased, featuring a clean white exterior complemented by a bright blue door. Lush green grass surrounds the property, adding a refreshing touch. A paved pathway leads to the entrance, with tall trees providing shade in the background.

Home in Gillespie Park

Downtown New Construction House

Guesthouse in Gillespie Park

An outdoor patio area is shown, featuring a round table with four red metal chairs. Potted plants flank the table, and string lights hang overhead, creating an inviting space. French doors lead into the interior, framed by lush greenery.

4.84 out of 5 average rating, 333 reviews

Sarasota Getaway Guest House

Guesthouse in Gillespie Park

An outdoor area is shown with a walkway made of red pavers leading to a yellow building. A dining set with an umbrella is situated on a gravel surface, surrounded by potted plants. Decorative stones and landscaping enhance the inviting outdoor space.

4.92 out of 5 average rating, 153 reviews

Perfect Florida location: Craftsman Carriage House

Guest suite in Port Charlotte

4.96 out of 5 average rating, 122 reviews

Garage to a Tiny House Studio Near Shopping Center

4.97 out of 5 average rating, 232 reviews

A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.

Apartment in Bayou Oaks

Modern Private Apartment 1 Block from Sarasota Bay

Family-friendly home rentals with a pool

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.

5 out of 5 average rating, 7 reviews

Paradise on Prospect w/ Htd Saltwater Pool

5 out of 5 average rating, 4 reviews

Heated Pool, Near Siesta Key Beach & Downtown

A spacious backyard area features a mini-golf course marked by small flags, inviting relaxation and play. Comfortable hanging chairs are under a stylish pergola, while a fun play structure is visible, enhancing the outdoor space designed for family-friendly enjoyment.

5 out of 5 average rating, 19 reviews

Private Oasis: Mini Golf and firepit. 2 king beds.

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

5 out of 5 average rating, 35 reviews

Sarasota Escape | Minutes to Beaches + Downtown

4.98 out of 5 average rating, 218 reviews

Condo in Longboat Key

Oceanfront on LBK!

5 out of 5 average rating, 118 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Luxury Villa with Pool, Game Room, Near Beach

Place to stay in Sarasota

A cozy seating area is featured with a modern electric reclining loveseat and a small bar table with two stools. Light from a nearby lamp provides illumination, while decorative artwork and a sign add a touch of charm to the neutral walls.

4.81 out of 5 average rating, 21 reviews

The Suite Retreat

A person is seated at the edge of a sparkling pool, facing the clear blue water. The poolside is tiled, and the sunlight reflects off the surface, creating a serene ambiance. The individual wears a swimsuit featuring a tiger stripe pattern.