Family-friendly holiday rentals in Downtown Sarasota

4.98 out of 5 average rating, 140 reviews

A quaint cottage features a vibrant red door, framed by lush greenery and colorful plants. The path leading to the entrance is bordered by neatly arranged brick landscaping, enhancing the inviting entrance to the home.

Home in Laurel Park

The Sweet Spot! Walk to DT & Free Trolley to Beach

Looking for the Sweet Spot in Sarasota? Look no further! This artistically updated cottage, nestled in the quiet, historic downtown neighborhood of Laurel Park is a just a short walking distance to some of the best downtown dining, shopping, arts venues and the renowned Selby Gardens. Take the free Breeze Trolley to Siesta Key and Lido beach. Relax in the private outdoor courtyard. It's is the perfect place for a couple's getaway, a family vacation, or a long term stay. So book now and welcome!

4.85 out of 5 average rating, 141 reviews

A light-filled living area features soft, neutral-toned sofas arranged around a glass coffee table atop a textured area rug. Decorative elements, such as a floral arrangement and softly glowing lamps, complement the inviting atmosphere. A doorway leads to the kitchen, enhancing the open layout.

Villa in Laurel Park

Updated Downtown Sarasota Villa, 2b/2b

Enjoy a stylish experience at this centrally-located 2 bedroom, 2 bathroom attached villa in historic Laurel Park, downtown Sarasota. New 75” smart TV! Sleeps 6. Bedroom 1: King bed w/ en suite bathroom. Bedroom 2: 2 queen beds. Granite kitchen. 2 bathrooms. Fenced outdoor paver patio w/washer & dryer. Updated 2022. Free parking outside villa. Walking distance to downtown Sarasota, Selby Gardens, Marina Jack, Main St & more. Pottery Barn furnishing, beachy vibe & free WiFi! Free parking too!

An inviting living space showcases a comfortable seating arrangement, including two black lounge chairs and a stylish dining area. Natural light floods through large windows, illuminating a decorative shelf filled with coastal decor. A circular rug adds a touch of warmth to the wood flooring.

4.96 out of 5 average rating, 131 reviews

5 Star! Walk/Bike DTN ~ 5 mi to Lido Beach Pets Ok

Bright & Comfy Downtown Home | Walk to Main St, Near Trolley to Lido Beach & St Armands. Centrally located in a quiet downtown neighborhood along the Legacy Bike Trail & Payne Park, this updated 3BR/2BA home is clean, cozy, and filled with coastal charm. Enjoy a screened-in lanai, a large, fenced backyard, WiFi, Smart TV with YouTube TV, BBQ, beach gear, washer/dryer and carport. Pets welcome! Prime Location: 1 mi to Main St dining. 2 mi to waterfront dining and boat tours. 5 mi to Lido Beach.

4.88 out of 5 average rating, 296 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

Guest suite in Downtown Sarasota

A colorful room features a green bed frame with a patterned comforter, complemented by a dark desk and a matching chair. A small black television is positioned on the desk, while a glass table adds an additional functional space. The walls are painted a warm yellow.

4.92 out of 5 average rating, 452 reviews

SUPER CLEAN 100% Private Downtown Location

A very private, quiet and secure space with a new comfortable Queen size bed, best of linens, 100% private attached bathroom and shower. Walk to downtown, waterfront and Payne Park. Complimentary bicycles, beach cooler, beach towels and umbrella! 100 Meg WiFi, large desk, LED TV. Delightful husband/wife "Superhosts" tend to your every need including complimentary bottled water, Starbucks coffee and Bigelow tea. We utilize the Airbnb and State of Florida anti-bacterial cleaning protocols.

4.95 out of 5 average rating, 133 reviews

Guest house in Sarasota

Downtown Garden Studio close to everything

Welcome to my brand new guest house! The original building has been rebuilt and completed in December 2024 to offer a more comfortable experience for my guests. Peaceful and centrally located, ideal for relaxation and easy access to explore historic Sarasota and the beaches. A quick drive, bike or a short walk to downtown Sarasota, Selby Botanical Garden and Pineapple Street antique shops. 1.5 miles to Sarasota Bay. 3.5 miles to St Armands Circle and Lido Beach. 6.5 miles to Siesta Key.

Guest house in Laurel Park

An outdoor common area features a decorative umbrella over a bistro table, surrounded by potted plants. A wooden deck leads to a staircase, with warm lights illuminating the setting. A grill is positioned nearby, creating an inviting outdoor space for relaxation.

4.97 out of 5 average rating, 504 reviews

Coolest Downtown Neighborhood - Ebikes, Beach Gear

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

4.93 out of 5 average rating, 307 reviews

The living area features a cozy sofa, two reclining chairs, and elegant decor. A TV is positioned above a media console, while a dining area is visible in the background. Large windows allow natural light to fill the space, highlighting the light wood flooring.

Home in Laurel Park

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota experience, combining downtown and beach attractions. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just a 5-minute ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! Certificate of Registration Number: VR24-00113

4.97 out of 5 average rating, 120 reviews

A well-lit bedroom features a spacious bed dressed in crisp linens, accented with an orange throw blanket. Two decorative wall sconces illuminate the room, while striped curtains frame the window, adding a modern touch. A woven basket and art pieces enhance the inviting decor.

Home in Gillespie Park

Mid-Century Circus Charm Near Downtown Sarasota

Retro circus romance & mid-century style near downtown Sarasota. ✅ Main Street, Downtown Sarasota 2 miles - 6 mins ✅ St. Armand’s Circle: 4.5 miles - 15 mins ✅ Lido Key Beach 5 miles - 15 mins ✅ Siesta Key Beach: 6 miles - 18 mins ✅ Downtown Bradenton 12 miles - 25 mins ✅ Bradenton Beach 14 miles - 30 mins ✅ Casey Key 16 miles - 30 mins ✅ Airport: Sarasota–Bradenton International Airport 6 miles - 12 minutes

Flat in Downtown Sarasota

A cozy sleeping area is showcased with a full-size bed adorned in white linens, complemented by decorative pillows. A large piece of art hangs above the bed, featuring abstract patterns and soft colors. A lamp illuminates the room, and a small window provides natural light.

4.81 out of 5 average rating, 330 reviews

Fun Hip Walkable Area by Opera/Water - Studio Apt.

Perfect for those on-the-go or planning to rest in bed & read; this small studio, has cuteness, w/amenities, full-size bed, coffee maker/small refrigerator/small microwave, closet with hangers and small bureau, tiled bathroom, books, hardwood floors, fan and ductless air/heat. Petite and best for one person but two if they love to snuggle. Historic area with shopping/dining/dancing, theaters, comedy club, markets, opera, free local transportation, Bayfront marina, tiki bar+more!

4.92 out of 5 average rating, 274 reviews

A welcoming entryway features a bright door with a small window and a decorative hanging piece. Light-colored walls surround a cozy seating area with a modern sofa. A simple side table holds a lamp, and framed artwork decorates the walls, complemented by indoor plants.

Home in Gillespie Park

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

Guest house in Laurel Park

A private outdoor area features a cozy swing sofa under a wooden pergola, surrounded by lush greenery. Several comfortable chairs are positioned around a small fire pit, creating a welcoming space for relaxation. Natural light filters gently through the surrounding trees.

4.89 out of 5 average rating, 149 reviews

City Garden Cottage

City Garden Cottage is a cozy and comfortable cottage located in the quiet Laurel Park neighborhood in Sarasota, only a few blocks from downtown. The studio is surrounded by lush gardens and trees with a Hot Tub. Inside, you will find a kitchenette equipped with a coffee maker, toaster, refrigerator, and hot plate. The studio also has a flat-screen TV, a queen bed & private bathroom. There is also shared use a gas grill, fire pit and Hot Tub included with the rental.

Popular amenities for Downtown Sarasota family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 15 reviews

A private pool area is showcased within a screened enclosure, featuring clear waters and sun loungers. Colorful umbrellas in red and green provide shade, while tall palm plants are arranged around the space. The adjacent home showcases large windows, offering views of the inviting outdoor area.

Home in Arlington Park

Sarasota's Luxury Oasis

4.98 out of 5 average rating, 170 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!

A heated saltwater pool is framed by light blue lounge chairs and a paved patio area. Gentle waves create a soothing effect at the pool's edge. Surrounding greenery and a clear blue sky enhance the outdoor retreat, providing ample space for relaxation and leisure.

4.95 out of 5 average rating, 62 reviews

Retro Beach House w/ Pool Walkable to downtown SRQ

4.97 out of 5 average rating, 122 reviews

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.

Home in Southgate

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

4.96 out of 5 average rating, 112 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

5 out of 5 average rating, 100 reviews

Home in Arlington Park

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

4.92 out of 5 average rating, 132 reviews

A mid-century structure is set among lush palm trees, showcasing a combination of wooden accents and large glass windows. A curved gravel driveway leads to the front entrance, inviting natural light into the living areas and offering a serene outdoor landscape.

Home in Saint Armands

St Armand's Mid-Century Oasis

Flat in Indian Beach-Sapphire Shores

The enclosed pool area is surrounded by lush greenery and tropical plants, with vibrant purple lighting creating a serene ambiance. A spacious swimming pool reflects the colors overhead, while a decorative wall clock adds a charming touch. Comfortable seating is present along the edges.

4.96 out of 5 average rating, 178 reviews

ROYS PLACE Romantic, Private, Paradise!

Family- and pet-friendly home rentals

The dining area features a wooden table set with placemats and a decorative tray, complemented by light-colored chairs. A small bouquet of flowers adds a touch of nature. The kitchen is visible in the background, showcasing cabinets and a stainless-steel dishwasher against a neutral wall.

4.92 out of 5 average rating, 49 reviews

Fully Equipped Beach Home Near Beaches/Downtown

Superhost

A charming exterior view showcases a single-story retreat surrounded by lush greenery and tropical plants. A gravel pathway leads to the welcoming entrance, framed by vibrant foliage. The natural light brightens the home, accentuating the mix of white and wooden siding.

Townhouse in Gillespie Park

4.89 out of 5 average rating, 9 reviews

Downtown Living, Steps to Parks, Newly Furnished

Flat in Indian Beach-Sapphire Shores

A spacious living area is featured with a large flat-screen television mounted on the wall. Two comfortable chairs are placed adjacent to a round ottoman, decorated with a variety of plants and a small basket. Natural light filters in through large windows, offering a view of the surrounding landscape.

4.97 out of 5 average rating, 163 reviews

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

5 out of 5 average rating, 23 reviews

An aerial view captures a modern apartment complex adjacent to a calm waterway, framed by lush greenery. The sunset casts warm hues across the sky, while nearby city lights begin to emerge. Boating docks and waterfront properties are visible in the serene landscape.

Flat in Sarasota

Zen and Paradise-Sarasota

A bright living area features a large flat-screen TV mounted on a light wall, with natural light flowing through multiple windows. Comfortable seating options include a spacious couch and two armchairs, complemented by a decorative side table and tropical plants.

4.98 out of 5 average rating, 42 reviews

Historic Downtown Sarasota - Gem I

4.95 out of 5 average rating, 55 reviews

Serenity Springs | Private Heated Pool + Waterfall

An open living area features a comfortable seating arrangement, including a sofa and armchairs. A medium-sized table is situated in front of the sofa, with a flat-screen television mounted on the wall. An adjacent kitchen, highlighted by a large island with two bar stools, is visible.

4.96 out of 5 average rating, 56 reviews

Sarasota Coastal Cottage

Superhost

5 out of 5 average rating, 4 reviews

Beach Life + Heated salt pool | Downtown + lg yard

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 48 reviews

The outdoor space features a private heated pool surrounded by a spacious patio made of pavers. A floating chipping green is positioned near the pool, with sun loungers arranged for relaxation. A shaded dining area is also visible, perfect for outdoor meals.

Home in Alta Vista

Palm Breeze Luxury•Heated Pool -Great for Families

A bright and inviting outdoor space features a saltwater pool surrounded by landscaped areas. A large umbrella provides shade over a white lounge chair, while additional seating is positioned around the pool deck, all enclosed by a wooden privacy fence.

4.97 out of 5 average rating, 75 reviews

Modern coastal downtown home w/saltwater pool

Superhost

4.81 out of 5 average rating, 58 reviews

Heated Pool & Private Yard | 15 Mins to Siesta Key

4.98 out of 5 average rating, 46 reviews

A privately enclosed pool area features a sparkling pool surrounded by lush tropical landscaping. Several loungers provide comfortable seating, with paver stones creating a clean, defined space. Sunlight filters through the screened enclosure, enhancing the serene atmosphere of the space.

Home in Laurel Park

Downtown Sarasota Oasis w/ Heated Pool!

Home in Gulf Gate Estates

4.97 out of 5 average rating, 265 reviews

Your private retreat near Siesta Key Beach.

5 out of 5 average rating, 155 reviews

Home in Siesta Key

Beach, Village, Dock & Private Pool! One-of-a-kind

Apartment in Indian Beach-Sapphire Shores

A circular pool is surrounded by modern white buildings, with palm trees dotting the perimeter. The clear blue water reflects the sky, and a poolside lounge chair is positioned near the edge. Paved stones create a pathway around the pool area.

5 out of 5 average rating, 39 reviews

Chill Sarasota Hideaway