Family-friendly vacation rentals in Sarasota

4.95 out of 5 average rating, 103 reviews

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.

Home in Sarasota Springs

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

KitchenFamilyBackyard

4.99 out of 5 average rating, 243 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!

KitchenFamilyGrill

4.94 out of 5 average rating, 100 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!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Indoor spacesKitchenWalkability

4.95 out of 5 average rating, 197 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

Indoor spacesKitchenDecor

5.0 out of 5 average rating, 114 reviews

Home in Arlington Park

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.

Indoor spacesKitchenWifi

4.96 out of 5 average rating, 148 reviews

A spacious patio is highlighted by a heated pool, surrounded by a decorative stone border. Comfortable outdoor seating is arranged nearby, beneath string lights that create a soft glow. A serene water view and lush greenery are visible in the background, enhancing the outdoor ambiance.

Home in Bradenton

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Indoor spacesKitchenBackyard

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, 104 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

Indoor spacesFamilyAmenities

4.98 out of 5 average rating, 299 reviews

A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.

Guesthouse in Sarasota

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Indoor spacesFamilyBathroom

4.98 out of 5 average rating, 125 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. 🌴

FamilyIndoor spacesCleanliness

4.98 out of 5 average rating, 365 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!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Indoor spacesFamilyPool

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, 101 reviews

Modern Pool House Sealand 3/2 near Siesta

In this unique modern pool home, the relaxation starts from the moment you walk in. Easy access to popular places such as downtown, Siesta Key beach, and tons of shopping. Best grocery store in town Detwillers farm market is only 2 min away. Trader Joe's, Costco, Publix are all within 5 min. Safe and quiet neighborhood.

FamilyKitchenBeach

The image features a heated saltwater pool with a pink inflatable flamingo. Surrounding the pool are comfortable seating options, including fire pit seating. The vibrant indoor spaces are visible, showcasing a cozy living room with a turquoise color scheme and a game room with a retro arcade machine.

4.98 out of 5 average rating, 108 reviews

*Kid Friendly w/Heated Pool* Close to Beach*

Welcome to ☀️Sarasota Sunshine☀️! This family friendly, beautifully designed property is centrally located and offers a one of a kind experience. Sleeping up to 9 guests, this luxurious space offers comfort, amenities and is close to downtown Sarasota as well as numerous beaches.

KitchenFamilyGrill

Popular amenities for Sarasota family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 384 reviews

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

FamilyKitchenBeach

5.0 out of 5 average rating, 133 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

Indoor spacesKitchenCheck-in

5.0 out of 5 average rating, 13 reviews

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

FamilyIndoor spacesCondition

Superhost

5.0 out of 5 average rating, 4 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

Indoor spacesFamilyCleanliness

4.9 out of 5 average rating, 49 reviews

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

KitchenFamilyCheckout

4.98 out of 5 average rating, 49 reviews

Home in Arlington Park

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta

FamilyIndoor spacesDecor

5.0 out of 5 average rating, 21 reviews

Modern 4bd | Heated Pool | Hot Tub + Studio Suite!

Indoor spacesKitchenAccuracy

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.

Indoor spacesFamilyAmenities

Family-friendly home rentals with air conditioning

5.0 out of 5 average rating, 16 reviews

Good Vibrations Home

FamilyKitchenTV

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, 55 reviews

Sunshine House- Sarasota Pool Retreat

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 31 reviews

NEW Luxe Resort Home*XL Pool/Hot Tub*1 mi to Beach

KitchenIndoor spacesBathroom

5.0 out of 5 average rating, 22 reviews

Home in Arlington Park

The Bahia. Wellness House heated pool, spa, sauna

KitchenIndoor spacesCondition

4.98 out of 5 average rating, 42 reviews

Siesta Key Luxury 6BR Retreat with Pool

FamilyKitchenHeating

4.96 out of 5 average rating, 45 reviews

Home in Bradenton

The Florida Rooms

FamilyKitchenComfort

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.

5.0 out of 5 average rating, 37 reviews

The Palms Away

Indoor spacesKitchenCleanliness

4.95 out of 5 average rating, 20 reviews

Heated Pool and Spa Near Siesta Key

FamilyKitchenBackyard

Family-friendly home rentals with Wifi

Home in Downtown Sarasota

5.0 out of 5 average rating, 20 reviews

Modern Luxe On Legacy Trail | Pool + Rooftop Deck

FamilyIndoor spacesWalkability

5.0 out of 5 average rating, 33 reviews

Family Landing Spot/Pool/Arcade Games/Baby Gear

KitchenFamilyComfort

4.83 out of 5 average rating, 40 reviews

Home in Sarasota Springs

Quiet Family Home w/ Pool Near Pinecraft

Indoor spacesFamilySleep quality

4.93 out of 5 average rating, 91 reviews

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.

Home in Sarasota Springs

The Coral Cottage-heated pool, Siesta beach 15 min

FamilyKitchenCheckout

5.0 out of 5 average rating, 9 reviews

Home in Bradenton

Free Heat Pool+Grotto+Spa~Pickleball~Golf~KidSuite

FamilyNearbyCheckout

5.0 out of 5 average rating, 14 reviews

Home in Siesta Key

Siesta Key House, Pool & Hot Tub, 1 mile to beach

FamilyIndoor spacesQuiet

Home in Gulf Gate Estates

A screened lanai showcases a heated pool and spa, surrounded by twinkling string lights. Lounger chairs and outdoor dining furniture are positioned nearby. A grassy area is visible beyond the pool, while a pink inflatable floats in the water, enhancing the serene outdoor setting.

4.99 out of 5 average rating, 80 reviews

Coastal Home in Sarasota-8min from Siesta Key

Indoor spacesFamilyTV

A large screened pool area showcases a heated swimming pool surrounded by elegant marble tiles. Comfortable seating arrangements are visible on one side, with modern lighting suspended overhead. Lush greenery is present in the background, contributing to a serene outdoor space.