Family-friendly holiday rentals in Siesta Key

4.98 out of 5 average rating, 111 reviews

Home in Bradenton Beach

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

Indoor spacesFamilyAccess

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.

4.96 out of 5 average rating, 47 reviews

Siesta Key Retreat 1mi to Beach!

Plan your SW Florida retreat to this spacious 3-bedroom, 2-bath oasis, w/ private caged pool, nestled on a quiet, peaceful street, a perfect vacation getaway for families/groups seeking relaxation and fun! Ideally located in the heart of Siesta Key a little over a mile from the #1 Beach in America! With the prime location near shops, entertainment, & 4 minutes to Siesta Beach. This charming coastal home offers smart TV in every room & a suite of variety teas/coffee pods & fully stocked kitchen!

Indoor spacesKitchenWalkability

4.96 out of 5 average rating, 111 reviews

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day at the beach.

FamilyIndoor spacesAccess

4.95 out of 5 average rating, 146 reviews

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

Condo in Siesta Key

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

KitchenIndoor spacesBarbecue

4.94 out of 5 average rating, 100 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.

Indoor spacesFamilyAccess

A private pool area is surrounded by lush greenery, featuring a clear blue water pool and four lounge chairs positioned for relaxation. Umbrellas provide shade, enhancing the serene outdoor space. Tropical plants are situated along the edge, adding to the natural atmosphere.

4.98 out of 5 average rating, 119 reviews

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book

KitchenIndoor spacesBackyard

5.0 out of 5 average rating, 134 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

FamilyIndoor spacesLayout

4.95 out of 5 average rating, 197 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

FamilyKitchenLocation

4.95 out of 5 average rating, 419 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

FamilyKitchenParking

5.0 out of 5 average rating, 15 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.

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 41 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.

KitchenFamilyParking

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.

5.0 out of 5 average rating, 105 reviews

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

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

FamilyKitchenBiking

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

5.0 out of 5 average rating, 114 reviews

Home in Arlington Park

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

Indoor spacesFamilyValue

4.97 out of 5 average rating, 134 reviews

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

Condo in Siesta Key

Heated Pools & Spa · Private Beach + Bay Views

KitchenFamilyGetting around

4.98 out of 5 average rating, 161 reviews

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

Indoor spacesKitchenAir conditioning

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, 136 reviews

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

KitchenIndoor spacesBeach

4.99 out of 5 average rating, 114 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!

FamilyKitchenPets

4.98 out of 5 average rating, 125 reviews

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

Home in South Sarasota

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Indoor spacesKitchenQuiet

5.0 out of 5 average rating, 100 reviews

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

Condo in Siesta Key

Breathtaking Beachfront Views in Siesta Key

KitchenFamilyAccuracy

4.95 out of 5 average rating, 103 reviews

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.

Home in Sarasota Springs

Deja Blue Villa Salt Water Heated Pool & Spa

Indoor spacesFamilyCleanliness

Family- and pet-friendly home rentals

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, 108 reviews

Retreat by the Bay-Heated Saltwater Pool

FamilyKitchenWi-Fi

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, 139 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

FamilyIndoor spacesCheck-in

5.0 out of 5 average rating, 3 reviews

The Siesta Key Retreat - An Island Garden Oasis!

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 7 reviews

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

Indoor spacesFamilyHospitality

5.0 out of 5 average rating, 17 reviews

Siesta Key Village Home

Indoor spacesFamilySleep quality

4.9 out of 5 average rating, 50 reviews

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

FamilyIndoor spacesCleanliness

4.96 out of 5 average rating, 46 reviews

NEW! Renovated Pool Home Mins 2 Siesta Key Beach

FamilyKitchenNearby

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.

5.0 out of 5 average rating, 5 reviews

Rustic Sands - 650

KitchenQuietComfort

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 61 reviews

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.

Home in Arlington Park

Private Heated Pool Retreat for Two Families

KitchenIndoor spacesCheckout

4.94 out of 5 average rating, 31 reviews

Bike to Beach Double King Suites, Pool & Mini Golf

KitchenFamilyAccess

The property features a two-story home with a light-colored exterior and a welcoming set of stairs. Tropical palm trees and green foliage frame the entrance, which is accented by vibrant blue planters. A concrete driveway leads to the house, providing ample space.

4.99 out of 5 average rating, 75 reviews

Quiet luxury on Siesta Key!

Indoor spacesKitchenWalkability

4.96 out of 5 average rating, 45 reviews

Home in Arlington Park

Modern Home Heated Pool near Siesta & Downtown

KitchenFamilyBarbecue

5.0 out of 5 average rating, 4 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

Indoor spacesFamilyDecor

5.0 out of 5 average rating, 17 reviews

Newly Remodeled Home w/ Pool in Siesta Key

KitchenFamilyBeach

5.0 out of 5 average rating, 5 reviews

At Sun Sea Terrace | Steps to Siesta Key Beach

FamilyHot tubLocation