Family-friendly holiday rentals in Southgate

The living and dining area features a spacious sectional couch with a decorative pillow, a coffee table, and a dining table with six chairs. A large flat-screen TV is mounted on the wall, and natural light floods in through sliding glass doors that lead to the backyard.

4.91 out of 5 average rating, 104 reviews

Oasis close to beaches & Downtown

This beautifully renovated, spacious home is in an awesome location! It's only 3 miles to the vibrant downtown Sarasota. Only about 6.5 miles to the famous Siesta Key Beach and Lido Key Beach as well as upscale shopping and dining at St. Armand's Circle. And 8 miles to SRQ airport. If you become tired of the beaches and exploring all of the restaurants, cook in the fully equipped kitchen or cook out in the fenced backyard with your kids (with & without fur). Relax & enjoy the beautiful weather

4.97 out of 5 average rating, 126 reviews

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

A Florida wellness retreat>>> Discover the charm of our delightful cottage, exceptionally placed amidst lush greenery! The interior offers an inviting ambiance with its plush, comfortable furnishings and a well-equipped kitchen with an espresso machine. Quietly nestled away from the hubbub of city life, our cottage offers a tranquil escape yet is in close to local attractions. Relish the day exploring charming seaside villages and beaches or simply bask in the serenity of your private haven.

4.88 out of 5 average rating, 255 reviews

An aerial view showcases a private island surrounded by water, featuring lush greenery and two tiny homes. A manicured lawn is visible with seating areas, umbrellas, and pathways that create a serene outdoor environment.

Tiny home in Sarasota

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

A living room area is shown, featuring a light-colored couch positioned beneath two large windows. Natural light filters in, highlighting a small potted plant on a coffee table topped with a woven textile. A lamp and a dark wood side table are also present, adding to the room's ambiance.

4.96 out of 5 average rating, 158 reviews

★1 BLOCK TO SIESTA DRIVE★KING BED★FULL KITCHEN★

Perfect hub for Sarasota travelers. Private separate apartment just 2 blocks away from Siesta Drive, 3.4 miles to Siesta Key Beach, and 5 minutes drive to Marina Jacks and Downtown area. • 55" 4k TV in living room • King size bed in bedroom • Fully equipped kitchen • Extremely safe neighborhood • Onsite parking for 1 vehicle • WiFi • 12 mins from SRQ Airport *Sarasota has numerous beaches. Red tide may be temporarily on one beach but not another. Please check the RedTide app while here.

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, 124 reviews

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

Welcome to Siesta Fiesta, where dreams of relaxation become reality. With the backyard heated pool and hot tub, you have your own oasis to channel inner peace. If you’re feeling froggy, hop over to the beaches, take a kayak tour through the mangroves, a beautiful chartered sunset cruise, or try some of the local eateries that guests rave about! Whether you want to stay in, or go out, this home offers you everything you could need or want and will satisfy for pure relaxation or adventure!

Superhost

A bright kitchen area features pale green walls and modern white cabinetry. A sign spells out "BEACH" in decorative letters, accompanied by textured decorative objects. A stainless-steel refrigerator and microwave are visible, highlighting the suite's inviting and fully equipped kitchen.

4.79 out of 5 average rating, 318 reviews

Close to Beach w/ Fenced in Backyard

Experience Sarasota like never before in our studio. Immerse yourself in the seaside charm while enjoying the comfort of a home away from home. Perfectly situated in the heart of Sarasota, you'll have easy access to all the must-see attractions, from the pristine Siesta Key beach to the bustling downtown area. Plus, with Sarasota Bay, Marina Jacks, top-rated restaurants, and grocery stores just a stone's throw away, everything you need is within reach. Come live the Florida dream!

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.95 out of 5 average rating, 155 reviews

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

A single-story home is showcased with a light exterior and grey roof. Blue shutters adorn the windows, while lush greenery and colorful landscaping enhance the front yard. A screened wraparound porch offers additional outdoor space. The property is bordered by a paved walkway.

4.95 out of 5 average rating, 103 reviews

Sarasota 2B/2B Near Siesta Key/Arlington Park/SMH

This newly renovated property is equipped with 2 bedrooms and 2 full bathrooms, full kitchen with all appliances, washer/dryer, screened wraparound patio, and fenced-in yard. Safe and beautiful walking neighborhood - 15 minute walk to Arlington Park and Recreation Center. 7 minute walk to Sarasota Memorial Hospital and Southside Village restaurants & shops. 15 minute drive to Bayfront Park, Selby Botanical Gardens, Marina Jack, St. Armand's/Lido Key and Siesta Key Beach.

4.84 out of 5 average rating, 277 reviews

A spacious living area is illuminated by natural light streaming through large windows. A comfortable sofa is centered in the room, adorned with decorative pillows. A stylish coffee table rests on a light rug, with an orange door adding a pop of color to the backdrop.

Bungalow in Sarasota

Charming Mid-Century Retreat by Arlington Park

A newly updated jewel in the heart of Sarasota's historic South Gate neighborhood, this newly renovated, bright home stands as a testament to the mid-century boom that shaped Sarasota. With 2 bedrooms, 1 bathroom and a separate office/sunroom with doors should you need quiet while working on vacation, it has it all. Positioned perfectly, our location boasts more than just the city's dynamic arts scene, delectable eateries, and beaches. Arlington Park is a block away.

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 125 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

4.96 out of 5 average rating, 447 reviews

Adorable studio close to Siesta beach!

Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away

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.

4.94 out of 5 average rating, 108 reviews

Sea Esta | Private Saltwater POOL + Putting Green!

BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table

Popular amenities for Southgate family-friendly rentals

Kitchen

Wifi

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, 173 reviews

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

Superhost

5 out of 5 average rating, 3 reviews

Luxury BeachHouse w/ Pool Spa & Direct Park Access

4.98 out of 5 average rating, 173 reviews

An outdoor area is showcased featuring a heated saltwater pool surrounded by lounge chairs. A vibrant play structure adds a playful element, while a hot tub is positioned nearby. Tropical landscaping complements the relaxing atmosphere, offering a family-friendly space for leisure and enjoyment.

Home in Bellevue Terrace

LUXE home 6mi to Siesta w/ incredible pool area!

The exterior of the home is shown, featuring a light-colored facade and a welcoming front door. A large oak tree provides shade over the driveway, while a spacious lawn is visible in the foreground. The two-car garage is accessible on the right.

4.95 out of 5 average rating, 57 reviews

Warm, Luxury Oasis in Central Sarasota

A covered outdoor gazebo area is highlighted, featuring a hot tub and comfortable seating. Palms and flowering plants frame the space, while a clean pathway leads through light gravel. The atmosphere is designed for relaxation and family gatherings alongside a spacious, fenced backyard.

4.98 out of 5 average rating, 58 reviews

Siesta Getaway-few mins to Siesta/hot tub/King bed

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.

4.96 out of 5 average rating, 114 reviews

The Animal House

5 out of 5 average rating, 102 reviews

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

4.88 out of 5 average rating, 169 reviews

A private pool area is surrounded by palm trees and shaded by umbrellas. The inviting water reflects blue skies, while a colorful float adds a playful touch. Comfortable seating is arranged around the pool, creating a relaxed outdoor atmosphere.

Home in Bradenton

Spring is in the air - HTD Pool*Hot Tub*Game RM

Family- and pet-friendly home rentals

The exterior of the villa is displayed, featuring a welcoming blue-green door and two large windows framed in white. A small potted plant accents the entrance, while a pathway leads to the door, surrounded by well-maintained grass and greenery.

4.87 out of 5 average rating, 127 reviews

Charming Villa 14 mins away from Siesta Key Beach

4.71 out of 5 average rating, 41 reviews

Beach Bum Bungalow-Sarasota-10 min to Siesta Key

A spacious living area is furnished with a dark sectional sofa and a wooden coffee table, adorned with a floral arrangement. Light streams through large windows, brightening the neutral-toned walls and tiled flooring. A dining area with metal chairs is visible in the background.

4.86 out of 5 average rating, 105 reviews

Charming In-Town Home Near Siesta Key

Superhost

A well-lit living area features an open layout with light wood flooring. Modern white cabinetry surrounds a spacious kitchen island, while large windows provide natural light. A contemporary seating area with a TV is visible, and soft fabric drapes complement the decor.

4.84 out of 5 average rating, 103 reviews

Elegant Home Central to Town, Parks & Beaches

A spacious outdoor dining area features a large table surrounded by six chairs, positioned on a light blue surface. In the background, a crystal clear pool reflects sunlight, while an umbrella provides shade. A fenced perimeter and greenery enhance the setting's privacy.

4.93 out of 5 average rating, 138 reviews

Centrally located oasis.

A private solar-heated pool is framed by a spacious patio featuring terracotta tiles. Colorful lounge chairs are arranged beside the pool, and glass doors lead into the living area. A shaded seating area offers comfort under the overhang, enhancing the outdoor space.

4.81 out of 5 average rating, 90 reviews

Best Location, Clean,w/ Fenced Yard & Private Pool

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, 127 reviews

Sunshine House, near Downtown, Legacy Trail, Beach

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, 108 reviews

Siesta Breeze ~ Charming Coastal Cottage

Family-friendly home rentals with a pool

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 out of 5 average rating, 87 reviews

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

4.98 out of 5 average rating, 105 reviews

Family Friendly w/Free Heated Pool Near Beach

5 out of 5 average rating, 8 reviews

Siesta Key 3BR w/ Heated Pool, Game Room & Lanai

5 out of 5 average rating, 6 reviews

Private Pool +Game Room Near Siesta Key | Sleeps 9

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.

4.97 out of 5 average rating, 79 reviews

GARDEN VIEW HOUSE WITH A POOL

A private heated pool is surrounded by a spacious patio featuring light-colored pavers. Two lounge chairs positioned under teal umbrellas invite relaxation. A white fence provides privacy, and lush greenery is visible in the background under a clear blue sky.

4.93 out of 5 average rating, 42 reviews

Coastal Comfort Getaway, Heated Pool!

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.

4.98 out of 5 average rating, 47 reviews

Private Heated Pool Retreat for Two Families