Family-friendly vacation rentals in Sarasota

The outdoor pool area features a heated pool and spa, surrounded by a screened lanai. Lounge chairs are positioned nearby for relaxing. A hammock rests on the grass, inviting moments of leisure. Lush greenery enhances the tranquil environment.

4.95 out of 5 average rating, 102 reviews

Deja Blue Villa Salt Water Heated Pool & Spa

Featured Home: 🌊 Deja Blue Villa 🌊 From the beautiful, fully-equipped kitchen, to our fenced and heated pool patio, Deja Blue Villa is your perfect vacation home! Located only 20 minutes from Siesta Key Beach and 25 minutes from Lido Key Beach, this incredible stay includes: Private Heated Pool & Spa + Lounge Chairs & String Lights Pool Patio Mini Fridge + Serving Area Free Washer/Dryer Access, Detergent & Softener Included Gas Grill + Propane Coffee & Coffee Maker TV + Roku in Every Bedroom

4.96 out of 5 average rating, 110 reviews

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day at the beach.

5.0 out of 5 average rating, 132 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

A serene view of the pool area features clear blue water, framed by a brick border. Lush greenery surrounds the pool, with a statue placed amidst the landscaping. Sunlight filters through the trees, casting soft reflections on the water's surface.

4.98 out of 5 average rating, 122 reviews

The Oasis

Welcome to The Oasis, your Florida home away from home! Centrally located, between siesta key and st Armand’s circle, near many fantastic restaurants, grocery stores, and downtown. This home has everything you need for a fantastic stress free stay in Sarasota. A luxurious Italian style pool and garden area, a spacious indoor area with a full sized kitchen, king bed, queen bed, 2 twin beds and 2 twin air mattress. 3 smart tvs. We love this stunning and cozy home and we’re sure you will too!

4.95 out of 5 average rating, 196 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

5.0 out of 5 average rating, 112 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

Welcome to The Blessing House, a beautifully curated Sarasota retreat designed for relaxation, comfort, inspiration, and quality time together. Enjoy a heated pool & spa, lush lanai, bright designer interiors, and a peaceful residential setting just 15 minutes from Siesta Key, Lido Key, and downtown Sarasota. Thoughtfully maintained and enjoyed by our family throughout the year, this home is ideal for couples, families, and discerning travelers seeking a restful and memorable getaway.

4.99 out of 5 average rating, 140 reviews

Home in Bradenton

Resort Style Retreat, Pickleball, Htd Pool, Play.

- FREE POOL HEAT, private pool - PICKLEBALL COURT in our back yard. - 2 King Beds, Queen sleeper sofa, 2 bunk beds - Close to Anna Maria Island - 7.3 miles to IMG Academy - Large back yard fully fenced - BBQ Grill - Outdoor TV - Corn toss - Ping Pong - Boardgames - Outdoor dining table - 1 mile from Robinson Preserve: kayak rentals, nature hiking, running, and playgrounds - Beach chairs, beach towels, cooler, umbrella provided. - pack n play, high chair - Smart TV in every room

5.0 out of 5 average rating, 8 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.

5.0 out of 5 average rating, 31 reviews

Heated pool+near beaches+arcade+hammocks+pooltable

Welcome to Magellans Oasis! Soak up the Florida sun in this newly renovated pool home designed for comfort, fun, and relaxation. Inside, enjoy bright living spaces with multiple smart TVs, a game room with a pool table, and a fully stocked kitchen. Step outside to your private heated pool surrounded by hammocks, lounge chairs, and a mini golf. With beach gear, family-friendly amenities, and a safe neighborhood, you’re close to downtown Sarasota and world-renowned beaches.

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5.0 out of 5 average rating, 103 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

4.95 out of 5 average rating, 42 reviews

Modern Home Heated Pool near Siesta & Downtown

Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!

4.98 out of 5 average rating, 123 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 Sarasota family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 45 reviews

Family Fun•POOL•Sleep 14•Game•SRQ, Ami &Beaches

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.

5.0 out of 5 average rating, 46 reviews

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

4.98 out of 5 average rating, 42 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

Home in Downtown Sarasota

5.0 out of 5 average rating, 18 reviews

Modern Luxe On Legacy Trail | Pool + Rooftop Deck

Home in Downtown Sarasota

The Master Suite features a spacious bed with a headboard, accompanied by two bedside lamps and minimalist decor. A cozy bench is positioned at the foot of the bed. Natural light brightens the space, which includes an ensuite bathroom with a walk-in shower visible in the background.

5.0 out of 5 average rating, 51 reviews

Coastal Contemporary Pool Home

4.94 out of 5 average rating, 98 reviews

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.

Home in South Sarasota

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

5.0 out of 5 average rating, 19 reviews

The Bahia. Wellness House heated pool, spa, sauna

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.

4.95 out of 5 average rating, 60 reviews

Private Heated Pool Retreat for Two Families

Family-friendly home rentals with air conditioning

5.0 out of 5 average rating, 4 reviews

*The Cronley House with Heated Pool

5.0 out of 5 average rating, 33 reviews

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

5.0 out of 5 average rating, 41 reviews

Villa in Bradenton

Lilo & Stitch Ohana Villa|Heated Pool Near AMI

4.88 out of 5 average rating, 65 reviews

An outdoor dining area features a large rectangular table with seating for eight, complemented by a shaded lounge space. A heated pool is visible, along with a sunken hot tub and sun loungers. Lush greenery surrounds the area, providing a serene backdrop.

Villa in Arlington Park

Bohemian Inspired Villa with Golf Cart and SUV

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.

5.0 out of 5 average rating, 72 reviews

Sarasota Memories For a Lifetime

A spacious seating area features comfortable chairs surrounding a modern fire table. A clear view of the salt water heated pool is available through large glass doors. Outdoor furniture is positioned beside the pool, with lush greenery visible in the background.

5.0 out of 5 average rating, 54 reviews

Sunshine House- Sarasota Pool Retreat

A screened lanai features an inviting heated pool surrounded by lounge chairs. Colorful hats rest on two chairs, while an outdoor umbrella provides shade. Lush greenery and a wooden fence create a private setting, with a BBQ grill visible in the background.

5.0 out of 5 average rating, 28 reviews

Perfect Reviews: Clean, quiet, pool, near Lido Key

5.0 out of 5 average rating, 3 reviews

Home in Siesta Key

The Siesta Key Retreat - An Island Garden Oasis!

Family-friendly home rentals with Wifi

5.0 out of 5 average rating, 4 reviews

Home in Bradenton

The Rainbow Lagoon | Pickleball, Heated Pool, Golf

5.0 out of 5 average rating, 16 reviews

The Ringling House | Pool, Pickleball & Beach

A private pool area is surrounded by a well-maintained yard featuring palm trees. Four lounge chairs are positioned near the pool, which is characterized by clear turquoise water. A white fence provides privacy around the space, enhancing the tranquil outdoor setting.

4.93 out of 5 average rating, 89 reviews

The Coral Cottage-heated pool, Siesta beach 15 min

5.0 out of 5 average rating, 19 reviews

Private Pool +Game Room Near Siesta Key | Sleeps 9

4.63 out of 5 average rating, 8 reviews

Home in Saint Armands

Beautiful Historic Ringling house!

5.0 out of 5 average rating, 20 reviews

Home in Bradenton

Sunwashed Stone Villa | Pool • Mini Golf • Luxury

4.99 out of 5 average rating, 75 reviews

The property features a two-story home with a light-colored exterior and a welcoming set of stairs. Tropical palm trees and green foliage frame the entrance, which is accented by vibrant blue planters. A concrete driveway leads to the house, providing ample space.

Home in Siesta Key

Quiet luxury on Siesta Key!