Family-friendly holiday rentals in Siesta Key

5 out of 5 average rating, 6 reviews

Steps to Siesta Key Beach! Sunset Balcony Views!

This beautifully appointed 2-bedroom, 1-bath condo (Sleeps 6) is centrally located directly across from the world-famous "sugar-white sands" of Siesta Key Beach. Unit 205 offers a perfect location with spectacular Gulf of Mexico sunsets from your private balcony. Enjoy a covered parking spot. The master suite has a King bed, a second bedroom with two twin beds, and a pull-out sofa in the living area. Nearby find rentals for bikes, scooters, water sports, parasailing, fishing, sunset cruise.

4.98 out of 5 average rating, 44 reviews

Coastal Luxe, SaltPool/heatSpa, 5 miles to Siesta

BRAND NEW home centrally located in the highly sought-after neighborhood of Arlington Park 2 miles to downtown. Coastal Luxe is a 2 story single family home with an open floor plan with bright, warm and inviting areas for gathering, entertaining, & relaxation. Every room in the house thoughtfully designed for your comfort & enjoyment. Perfect for your large group of friends & family!. Pool & Spa, Outdoor kitchen equipped with gas grill & smoker Enjoy your own mini golf experience with 4 holes

4.94 out of 5 average rating, 94 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.

5 out of 5 average rating, 8 reviews

Luxury 3B/3B waterfront home w/ pool + boat access

Escape to this luxurious 3BR/3BA Sarasota sanctuary! 5 minutes from Siesta Key, this Mid-Century Modern gem sits on a canal with direct Bay access (no bridges). Dive into the private pool & spa, lounge on the 1,000 sq ft porch, or relax inside on cozy furnishings. Includes a private dock, kayak/SUP/canoe, bikes, and a massive driveway for boat trailers. From the hanging bed swing to the gourmet kitchen, every detail is designed for your dream waterfront getaway. Your Florida paradise awaits!

5 out of 5 average rating, 131 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

4.86 out of 5 average rating, 108 reviews

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

Condo in Siesta Key

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

4.95 out of 5 average rating, 195 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

5 out of 5 average rating, 7 reviews

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

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.

4.93 out of 5 average rating, 163 reviews

Siesta Key Beach & Village 2BR/2BA Steps to Beach

This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.

4.97 out of 5 average rating, 38 reviews

Luxury Canal-Front Home + Heated Pool Near Beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.

A private heated pool is surrounded by lush palm trees and a well-maintained lawn. An outdoor dining area with a large umbrella is visible, along with two lounge chairs positioned near the pool. The area is brightened by clear blue skies and sunlight.

5 out of 5 average rating, 164 reviews

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

Rad’s Cozy Cottage – Siesta Key Private Home. Enjoy a heated saltwater pool, canal-front dock, and putting green at this one-of-a-kind tropical getaway. Steps from Siesta Village (shops, restaurants, nightlife) and the powdery-white sands of Siesta Key Beach. Fully updated 2BR/1.5BA cottage with modern kitchen, AC, Wi-Fi, and washer/dryer. Sleeps 6 (king + 2 twins + sofa). Book your island paradise!

4.98 out of 5 average rating, 121 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. 🌴

Popular amenities for Siesta Key family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 160 reviews

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

5 out of 5 average rating, 111 reviews

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

Superhost

A spacious kitchen area features sleek cabinetry and a large center island with a striking stone surface. Wooden beams add a rustic touch overhead, while modern appliances are seamlessly integrated. Natural light floods the space, creating an inviting environment for meal preparation and gathering.

5 out of 5 average rating, 4 reviews

Rustic Sands - 650

4.92 out of 5 average rating, 150 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

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.

4.98 out of 5 average rating, 147 reviews

Cozy Boho Bungalow Pool/Spa Downtown Sarasota

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, 130 reviews

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

5 out of 5 average rating, 13 reviews

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

4.99 out of 5 average rating, 110 reviews

An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.

Cottage in Sarasota

Quaint Cottage,150 steps away from Crescent Beach!

Family- and pet-friendly home rentals

Superhost

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.94 out of 5 average rating, 105 reviews

Retreat by the Bay-Heated Saltwater Pool

4.93 out of 5 average rating, 28 reviews

Coastal Luxury*Pool*Hot Tub*Sunsets*Close to Beach

Superhost

5 out of 5 average rating, 4 reviews

Gertrudes Siesta, Beach-view, Pool,1 min to Beach

5 out of 5 average rating, 7 reviews

Casa Del Mar - Luxury Home w/ Private Heated Pool!

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.

4.95 out of 5 average rating, 134 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

4.9 out of 5 average rating, 41 reviews

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

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 out of 5 average rating, 44 reviews

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

5 out of 5 average rating, 10 reviews

Apartment in Siesta Key

Siesta Key Luxury Penthouse, walk to Beach&Village

Family-friendly home rentals with a pool

5 out of 5 average rating, 14 reviews

Home in Anna Maria

Magnolia Palms: Family Retreat w/ Backyard Oasis

A serene backyard oasis is depicted, featuring a private heated pool surrounded by lush palm trees. An outdoor fire table sits in the foreground, with comfortable seating arranged to create an inviting gathering space. The spacious two-story home can be seen in the background.

5 out of 5 average rating, 15 reviews

Siesta Soul | Located in Siesta Key Village

5 out of 5 average rating, 19 reviews

The Bahia. Wellness House heated pool, spa, sauna

A spacious kitchen showcases a large island with seating for four, surrounded by light-colored cabinetry and modern appliances. Natural light illuminates the area through large windows, providing a view of the outdoor pool. Decorative tiles and subtle backsplash add texture to the design.

4.95 out of 5 average rating, 43 reviews

Siesta Key Retreat 1mi to Beach!

4.99 out of 5 average rating, 95 reviews

Heated pool & Infrared Sauna, 2 min to beach

4.96 out of 5 average rating, 27 reviews

Bike to Beach Double King Suites, Pool & Mini Golf

5 out of 5 average rating, 31 reviews

Near Siesta Key | Palm-Lit Nights, Pool & Spa

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.