Family-friendly holiday rentals in The Meadows

4.98 out of 5 average rating, 103 reviews

A cozy living area features a light blue wall, with a comfortable white sofa arranged around a neutral-toned rug. In the foreground, a wooden dining table with four chairs provides seating. Natural light enters through a doorway that leads to an outdoor space.

Guesthouse in Bradenton

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

KitchenIndoor spacesCleanliness

An outdoor area features a heated pool surrounded by a spacious deck. Lounge chairs are positioned nearby for relaxation, and a dining set offers seating for outdoor meals. A screened enclosure provides protection from insects while allowing natural light to filter through.

4.91 out of 5 average rating, 138 reviews

Heated 3BR Pool Home Glen Oaks | Close to Downtown

Family-friendly pool home near Bobby Jones Golf Club, perfectly located in the heart of Sarasota. You’re less than 10 minutes from top attractions, dining, and shopping, Downton Sarasota and just a short drive to the world-famous Siesta Beach or Lido Beach. This private home features its own entrance, a heated pool, and a fully fenced backyard—ideal for families and added privacy. We’re pet-friendly too! Comfortable, central, and close to everything—perfect for your Sarasota getaway VR24-00164

Indoor spacesFamilyWalkability

4.95 out of 5 average rating, 198 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 spacesKitchenCleanliness

A covered patio area features modern wicker furniture with white cushions, positioned around a glass coffee table. The inviting space overlooks a pristine pool, surrounded by a protective screen. Lush greenery is visible in the background, enhancing the tranquil setting.

4.96 out of 5 average rating, 149 reviews

Luxury Pool Family Oasis-Siesta Key/DT 3BR/2BA

Welcome to your home away from home! This renovated, spacious, and bright pool home will immerse you in a luxurious experience the minute you arrive. Located on a lush, quiet street, yet close to all of Sarasota's best attractions! Close to Siesta Key Beach (#1 beach in the USA), 10 minutes to downtown (with fantastic restaurants and shopping), and within walking distance of the famous Fresh Fish Waltz Market. Easy I-75 access, Nathan Benderson Recreational Lake Park, and the new UTC mall!

KitchenFamilyHospitality

A private saltwater pool is enclosed by a screened patio, featuring clear, inviting water. Sunlight reflects off the surface, creating a calming atmosphere. Surrounding greenery provides a natural backdrop, enhancing the serene environment. A lounge chair is visible next to the pool.

5.0 out of 5 average rating, 123 reviews

Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)

✨ Fully Renovated & Stylish! ✨ Family & Dog-Friendly | Single-Story | Private Saltwater Pool | Secluded Backyard. Enjoy the charm of Sarasota in our completely updated home off University Parkway. Bright, open spaces with new furniture, perfect for relaxation. Features a heated saltwater pool in a private, fenced yard. Close to beautiful beaches—10 miles to N. Lido Beach and 13 miles to Siesta Key Beach. Conveniently located 4 miles from SRQ Airport, ideal for your next memorable get

FamilyKitchenAir conditioning

4.98 out of 5 average rating, 210 reviews

Secluded Cottage w/ Hot Tub Near UTC and NBP

Welcome to The Crew House! A brand new, stylish, cozy cottage that is walking distance to all that the Nathan Benderson Park and University Town Center areas have to offer! The property is on a 2 acre parcel so there's plenty of room to spread out. At our cottage you will find a comfortable bed, stylish furniture, high-end finishes, a large island, screened-in outdoor dining table, and a great outdoor space with a private hot tub. We also have a concept2 rower available in the garage.

Indoor spacesFamilyHospitality

4.94 out of 5 average rating, 314 reviews

Guest suite in Sarasota

MG Tropical Stay. Fully private, no shared spaces

Welcome to your modern Sarasota Guest Suite – Adults Only, Private & Peaceful 🌞 Remodeled on January 26, 2026, this private suite offers a separate entrance and parking for two cars. Enjoy a cozy queen bed, full bathroom, and a kitchenette with microwave, mini‑fridge, coffee maker, and more. Relax on your private patio with a solar shower. Stay cool with a quiet mini‑split A/C. We provide beach essentials: umbrella, chairs, cooler, and towels—perfect for your Sarasota beach days 🌴

KitchenFamilyDecor

4.84 out of 5 average rating, 477 reviews

Apartment in Sarasota

Sarasota’s Little Slice of Paradise

Welcome to our charming, fully furnished one bedroom apartment with its own private entrance. Attached to our home but completely separate, it has everything you need for a comfortable Sarasota getaway. The apartment features a queen size bed, comfortable couch and an air mattress. Kitchen has a full size fridge and oven. Guests are also welcome to enjoy our large pavilion - a great place to relax, barbecue, enjoy a meal or simply sit back and enjoy a good book.

KitchenIndoor spacesBathroom

5.0 out of 5 average rating, 107 reviews

A charming house with a well-manicured lawn is framed by lush greenery. The front porch is accented by decorative red doors, and a stone walkway leads up to the entrance. Large trees provide shade over the landscaped yard.

Home in Bradenton

Peaceful Braden River Oasis: Main House

Escape to our charming riverfront Main House—a spacious 2 bed, 2 bath retreat that sleeps up to 7. Enjoy stunning river views, a screened-in porch, and access to the peaceful river dock. With a master suite featuring an outdoor shower and a spacious lofted sleeping area, this home offers everything you need for a relaxing and memorable getaway. Part of a unique property with two other rental units—perfect for groups or families seeking tranquility and adventure.

Indoor spacesFamilyHospitality

A modern house is presented with a neatly manicured lawn and a driveway leading to a garage. Lush palm trees and potted plants frame the entrance, while large windows allow natural light to fill the interior. The structure has a welcoming white facade under a gray roof.

4.95 out of 5 average rating, 116 reviews

Casa Cruz-3RM/2BA w/Heated Salt Water Pool

You'll have a great time at this modern 3RM/2 BA house with a heated salt water pool. This beautiful home is located 6 minutes to SRQ Airport, 20 minutes to the #1 rated beach in the country, Siesta Key, 5 minutes to Publix and local restaurants, and 10 minutes to high-end shopping at UTC mall. You’ll have access to major FL highways. The home is equipped with all the essentials needed for short term/long term stays. Book your stay today! Casa Cruz es su Casa!

KitchenIndoor spacesTV

4.93 out of 5 average rating, 112 reviews

Sarasota central home near beaches.

Enjoy a stylish experience at this centrally-located home. Minutes away from SRQ airport, a 10 minute drive to downtown Sarasota and 15 minutes to Lido Beach. The perfect getaway surrounded by nature on a large private property with a designated work space. Open concept floor plan to enjoy cooking, dinners and movie nights with your loved ones. Exceptional interior design through out the home with warm touches to give you a relaxing and pleasant stay.

Indoor spacesKitchenLaundry

A charming 1920s cottage is set in a lush green landscape, accentuated by carefully arranged flowerbeds. The light yellow exterior is complemented by a white porch and a metal roof. The surrounding trees provide shade, creating a peaceful and inviting outdoor space.

4.97 out of 5 average rating, 138 reviews

Bright & Peaceful 1920s Cottage: Close to UTC!

Experience the timeless charm of this 1920s beautifully preserved cottage – where original details meet modern comforts. A bright & peaceful property nestled on half an acre with plenty of space to spread out, natural light that pours into every room, & a private fenced in yard - it's an ideal spot to entertain AND unwind. Whether you are headed to the beach, Benderson Park, Downtown or UTC mall, this neighborhood is central to anything you'll need!

KitchenFamilyCheck-in

Popular amenities for The Meadows family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.85 out of 5 average rating, 103 reviews

[The Paradise Palms] Salt Water Pool & Hot Tub

KitchenIndoor spacesBarbecue

4.96 out of 5 average rating, 125 reviews

The kitchen features modern cabinetry with glass-front doors, showcasing dishware and decorative items. A teal backsplash adds color above the wooden countertop, which includes a stainless-steel sink and various utensils. A small stool is positioned nearby for convenience.

Guest suite in Sarasota

The Animal House

Indoor spacesFamilyCheck-in

A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.

4.97 out of 5 average rating, 103 reviews

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indoor spacesKitchenBathroom

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.

4.97 out of 5 average rating, 158 reviews

Cozy Boho Bungalow Pool/Spa Downtown Sarasota

KitchenFamilyPool

5.0 out of 5 average rating, 117 reviews

Home in Arlington Park

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

Indoor spacesKitchenHot tub

4.85 out of 5 average rating, 107 reviews

A spacious outdoor area features a heated saltwater pool surrounded by a screened enclosure. A jacuzzi is attached to the pool, with multiple lounge chairs positioned for relaxation. Lush greenery lines the perimeter, enhancing the sense of privacy and tranquility.

Home in Bradenton

Stylish 6 Bed Pool Home with Golf Simulator & Spa

FamilyKitchenSleep quality

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, 135 reviews

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

KitchenIndoor spacesTV

4.97 out of 5 average rating, 140 reviews

Home in South Bradenton

Family Stay: Outdoor Theatre! Heated Pool | Spa

Indoor spacesKitchenView

Family- and pet-friendly home rentals

The exterior of a charming adobe-style home is highlighted, featuring a light blue facade and a decorative entrance. A pathway leads to the door, bordered by colorful plantings and a white picket fence. Tropical plants add to the serene ambiance of the front garden.

4.95 out of 5 average rating, 118 reviews

Casa de Zara| Downtown Sarasota- 5mi Lido Beach

KitchenIndoor spacesQuiet

Home in Gulf Gate Estates

Beachy Cottage close to Siesta | 3 Bed | Huge Pool

Indoor spacesKitchenQuiet

4.89 out of 5 average rating, 107 reviews

4.94 out of 5 average rating, 179 reviews

Lake Front House with a Pool

FamilyIndoor spacesPool

A welcoming entryway showcases a simple wooden console table with small potted plants. Above, a serene painting depicting a boat complements the neutral wall. The view to the right reveals a sun room filled with natural light, providing a connection to the private backyard.

4.95 out of 5 average rating, 195 reviews

Updated Ranch Near Beaches/Downtown - Pet Friendly

FamilyKitchenQuiet

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, 202 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

FamilyKitchenWi-Fi

The spacious living area features a comfortable couch adorned with patterned pillows, a wooden coffee table, and colorful rugs. Natural light floods in through large windows, and an open layout connects to the dining area and kitchen, which is visible in the background.

4.98 out of 5 average rating, 132 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

FamilyIndoor spacesView

4.99 out of 5 average rating, 142 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

KitchenFamilyBathroom

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

FamilyIndoor spacesAccess

Family-friendly home rentals with a pool

The outdoor area features a heated pool surrounded by lounge chairs, providing ample space for relaxation. A dining set is positioned nearby, accompanied by an umbrella for shade. Lush greenery and palm trees border the property, complementing the serene atmosphere.

4.91 out of 5 average rating, 122 reviews

Rhodes Retreat - Beautiful Pool and Backyard Space

FamilyKitchenLocation

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

FamilyKitchenLong stay

5.0 out of 5 average rating, 17 reviews

Good Vibrations Home

FamilyKitchenAmenities

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, 57 reviews

Sunshine House- Sarasota Pool Retreat

Indoor spacesKitchenComfort

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, 48 reviews

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

Indoor spacesFamilyQuiet

5.0 out of 5 average rating, 3 reviews

Campervan/RV in Sarasota

Mingo’s Micro Glamper!

BathroomHospitality

5.0 out of 5 average rating, 5 reviews

Home in The Meadows

Precise Realty presents The Meadows Estate Retreat

Indoor spacesFamilyLocation