Family-friendly holiday rentals in Sarasota Springs

A light-filled entryway features a wall of glass shelving with decorative items. Double glass doors provide access to the outdoor space, which is partially visible through the glass. A small mat lies on the floor near the entrance.

4.91 out of 5 average rating, 236 reviews

Sunshine Suite, Minutes to Beach,Tropical Paradise

The Sunshine Suite.Lots of natural light in this totally updated modern 3 bed/1 bath home.It is a completely separate dwelling w separate entry from the other dwelling on the property sharing no common walls. Smart thermostat & door lock. Keyless entry.Brand new AC, gas oven, quartz counter w/ custom marble backsplash, modern & comfortable furniture, private outdoor area, gas BBQ grill, off street parking.Great location! Minutes to Siesta Key beach, shopping/UTC, interstate, hospital & downtown

KitchenIndoor spacesComfort

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, 105 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

FamilyIndoor spacesAmenities

4.92 out of 5 average rating, 174 reviews

Cozy Heaven Studio III

Welcome to our cozy studio! *Attached to the Main House with its own Private Entrance!* Ideal for couples, it features a comfortable queen-size bed, a full bathroom, and a small kitchen equipped with everything you need for a fantastic stay✨ Enjoy your own private patio complete with a BBQ grill and beach gear for your convenience. Relax and unwind with a TV for your entertainment. We offer 1 designated parking spot Located 18 mins from Siesta Key, 23 mins from Lido Key & 1.5 miles from I-75😎

FamilyKitchenAccuracy

4.91 out of 5 average rating, 129 reviews

Coastal Farmhouse - 3/2 with heated saltwater pool

Experience relaxation at this tranquil 3BD/2BA home with a heated pool, perfect for a family retreat! Prepare meals in the fully equipped kitchen or savor local delights on the screened-in lanai. Each bedroom boasts plush bedding, ensuring a restful night's sleep. Plus, a cozy living room. Conveniently located, just under 9 miles from Siesta & Lido Key Beach, Der Dutchman 2.2 miles and 2.5 miles from Yoder's Restaurant. Shopping and dining options at University Town Center, only 7.7 miles away.

Indoor spacesFamilyBarbecue

A handcrafted wooden pelican figurine stands prominently on the countertop, adding a coastal touch. Above, pendant lights hang beneath a bamboo ceiling, providing a warm glow. The background reveals glimpses of a colorfully decorated space with various shelves and artwork.

4.96 out of 5 average rating, 118 reviews

Sandy Feet Retreat- Cozy Bungalow & Outdoor living

Welcome to Sandy Feet Retreat! Our single family home is located in Sarasota Florida, only 8 miles from Siesta Key, 5 miles from downtown Sarasota, and only one block away from the Legacy Trail. The perfect Sarasota Home for your trip, featuring a cozy coastal theme with amenities, including a hot tub, grilling station, fire pit, and outdoor entertaining area. Just 2 miles off I 75, this charming vacation home is a short drive from many local restaurant options. Enjoy all Sarasota has to offer.

Indoor spacesKitchenBeach

An outdoor dining area features a wooden table set for four, overlooking a pristine pool. Lounge chairs are positioned nearby, providing a relaxing space for sunbathing. The screened patio ensures comfort while enjoying meals or relaxation outdoors.

4.98 out of 5 average rating, 162 reviews

Heated Pool Oasis 3BR/2BA near Siesta Key Beach

Relax at this modern heated pool house located just 15 min from the famous Siesta Key Beach. Nested in a quiet neighborhood with a lot of privacy, the house has plenty of space for an entire family or a group of friends. An additional family room with a TV for kids. Relax by the pool in the spacious outdoor area or explore the beautiful downtown filled with restaurants. Recently renovated, this home offers handmade authentic Mexican tile flooring to compliment a cozy and contemporary design.

Indoor spacesFamilyPool

4.9 out of 5 average rating, 139 reviews

Bella - Raine Estates

Welcome to Bella-Raine! This home has plenty of space for your whole party to relax and feel comfortable. This home has been thoughtfully decorated and styled. Located to much of what Sarasota has to offer. Siesta key beach is 7.9 miles away, 15 - 20 minutes. Fenced in backyard. The Legacy Trail bike path is very close by, Smart TV in common area has HDMI cable. The kitchen area will be a favorite place for your family to gather. This home has three bedrooms on the main floor and two upstairs

Indoor spacesKitchenOutdoor spaces

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, 128 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!

KitchenFamilyHospitality

4.95 out of 5 average rating, 199 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

FamilyIndoor spacesCheckout

A private heated pool is enclosed within a screened area, featuring clear blue water. Red Adirondack chairs are positioned nearby on a structured surface. A spacious yard is visible beyond the pool area, enclosed by a wooden fence for added privacy.

4.82 out of 5 average rating, 230 reviews

Heated Open Pool Home In Sunny Sarasota!

This home is perfect for hosting friends and family or just relaxing on your own! Spend a day in the surf and sun at the world famous Siesta Beach, shop at one of the many centrally located shopping centers , try local restaurants, or just take it easy in your own private and open pool and sitting area! Like making your own meal, step inside to an updated and fully stocked kitchen! Two living rooms, lots of space. Let this beautiful home be yours during your visit to Sarasota!

KitchenFamilyLaundry

4.84 out of 5 average rating, 43 reviews

Quiet Family Home w/ Pool Near Pinecraft

Escape to a serene family retreat near Pinecraft and Yoders! This 3-bed, 2-bath home features a screened-in heated swimming pool for year-round enjoyment. Nestled in a quiet, family-friendly neighborhood, savor nearby Amish dining at Yoders and Der Dutchman. Siesta Key & Lido Key Beaches are only 8.7 miles away! Explore Marina Jack's at Bayfront Park in downtown Sarasota, where you can admire stunning boats and enjoy a leisurely stroll. Your perfect vacation awaits you!

KitchenFamilyLocation

An outdoor dining area features a large table set with plates and glasses, surrounded by seating. A pool is visible nearby, framed by lounge chairs under a covered patio with ceiling fans. The walls are painted in a vibrant blue, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 203 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

KitchenFamilyPool

Popular amenities for Sarasota Springs family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 127 reviews

Spacious 4BR Getaway – Perfect for Families!

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A hot tub is visible in the foreground, emitting a soft blue glow. In the background, a cozy lounge area is arranged with sectional seating and a fire-pit table, illuminated by string lights. Two hammocks are hung under a shaded canopy, adding to the inviting outdoor space.

4.91 out of 5 average rating, 188 reviews

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

Indoor spacesKitchenBackyard

Home in Gulf Gate Estates

A spacious backyard features a heated private pool surrounded by a paved area. Lounge chairs are positioned around the pool, with umbrellas providing shade. Lush greenery and a fence frame the yard, creating a serene outdoor setting, ideal for relaxation.

4.8 out of 5 average rating, 137 reviews

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Indoor spacesFamilyCheckout

5.0 out of 5 average rating, 117 reviews

Home in Arlington Park

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

KitchenFamilyNearby

Home in Gulf Gate Estates

4.96 out of 5 average rating, 134 reviews

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Indoor spacesFamilyOutdoor spaces

4.96 out of 5 average rating, 113 reviews

Sun-filled cottage with pool, walk to beach

FamilyIndoor spacesCondition

A screened lanai features a bubbling hot tub and comfortable seating area adorned with neutral-colored cushions. Soft lighting is offered by overhead string lights. Surrounding greenery enhances the peaceful ambiance, while large windows allow natural light to flow into the space.

5.0 out of 5 average rating, 209 reviews

Turtle Nest Oasis • Hot Tub • 5 mi to Siesta Key

KitchenIndoor spacesQuiet

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, 136 reviews

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

KitchenIndoor spacesBackyard

Family- and pet-friendly home rentals

4.84 out of 5 average rating, 477 reviews

Apartment in Sarasota

Sarasota’s Little Slice of Paradise

FamilyKitchenAir conditioning

Home in Gulf Gate Estates

4.89 out of 5 average rating, 107 reviews

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

KitchenFamilyAmenities

A pineapple plant is featured prominently in the foreground, with a small pineapple developing. In the background, the house is framed by greenery and a porch with white railings, complemented by soft natural lighting.

4.82 out of 5 average rating, 279 reviews

The Pineapple Suite.Teal tropical home in Sarasota

KitchenFamilyWalkability

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.85 out of 5 average rating, 131 reviews

Sarasota Getaway “Have some fun under the sun.”

Indoor spacesFamilyCondition

4.89 out of 5 average rating, 144 reviews

Residence in Sarasota

FamilyKitchenBackyard

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, 142 reviews

Siesta Breeze ~ Charming Coastal Cottage

Indoor spacesFamilyParks

4.91 out of 5 average rating, 171 reviews

Near Siesta Key | Quiet, Family-Friendly, 3 Beds

KitchenIndoor spacesLayout

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, 242 reviews

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

KitchenFamilyOutdoor spaces

Family-friendly home rentals with a pool

A heated saltwater pool is framed by a privacy fence, with lounge chairs positioned nearby. Lush palm trees add greenery to the space, creating an area for relaxation. The clear water reflects the sky, enhancing the tranquil ambiance of the outdoor setting.

4.85 out of 5 average rating, 220 reviews

~Flamingo House~3 br,3 bath, heated pool~

FamilyKitchenDecor

A private pool area is enclosed by a screened-in lanai, featuring clear blue water reflecting sunlight. A patio umbrella and several chairs are positioned nearby, surrounded by lush greenery, creating a relaxing outdoor space.

4.98 out of 5 average rating, 95 reviews

GARDEN VIEW HOUSE WITH A POOL

Indoor spacesFamilyBathroom

5.0 out of 5 average rating, 22 reviews

Private Heated Pool, 8.5mi to Siesta Key Beach

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 29 reviews

Sapphire Cove | Private Heated Pool + Hot Tub

FamilyIndoor spacesBeach

A screened-in pool area features sparkling water with a shallow entry. Comfortable seating is positioned around the pool, alongside an outdoor dining space. A basketball hoop is mounted at one end of the pool, and greenery provides a natural border to the serene setting.

4.84 out of 5 average rating, 91 reviews

Relaxing Outdoor Space w/ Pool

Indoor spacesFamilyParks

A heated pool is surrounded by lush greenery, featuring six lounge chairs and a large umbrella for shade. The patio area is accentuated with tropical plants, while a covered lanai is visible in the background, providing additional outdoor space.

4.99 out of 5 average rating, 100 reviews

You Private Tropical Paradise

FamilyIndoor spacesLocation

4.9 out of 5 average rating, 10 reviews

4 Bedroom/5 Bed/2 Bath- Tyne Haven +Saltwater Pool

FamilyIndoor spacesDecor

A screened-in pool area features a clear blue pool with a shallow entry. Sun loungers are positioned alongside the pool, and outdoor seating is arranged nearby. The space is bathed in natural light, creating an inviting atmosphere for relaxation.