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Kid-friendly vacation rentals in Leeward

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Leeward

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

The modern villa features a two-story design with a spacious ground-level patio. A private pool reflects the blue sky, surrounded by tropical landscaping. Comfortable outdoor seating is visible on the terrace, offering a quiet space for relaxation.

Villa in The Bight Settlement

4.98 out of 5 average rating, 135 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

A modern two-story villa is depicted, featuring a light grey exterior with large windows. A covered balcony is visible on the upper floor, adorned with decorative railing. Lush greenery surrounds the property, and a spacious driveway provides access to the entrance.

Home in Grace Bay

4.95 out of 5 average rating, 167 reviews

Follow Your Dreams Villa!

Follow Your Dreams – Private Villa Escape to this stylish villa designed for one couple. Enjoy a private pool surrounded by palms, a 65" TV, and a fully equipped kitchen with dishwasher and laundry. Located behind Coco Bistro/Coco Van and just 2 minutes by car to Grace Bay Beach, it offers a mix of privacy and convenience. This totally private villa is perfect for two guests seeking a serene and unforgettable tropical getaway. Book now to make your dream vacation a reality!

A modern villa is showcased, with its sleek design complemented by lush tropical landscaping. A private plunge pool is visible, surrounded by wooden decking and lounge chairs. A small outdoor dining area and a barbecue grill are also present, creating a relaxing outdoor living space.

Villa in Long Bay Hills

4.92 out of 5 average rating, 121 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Top guest favorite

The infinity edge pool reflects the vibrant colors of the sunset, overlooking Juba Sound. Lush greenery surrounds the area, enhancing the serene atmosphere. The horizon features a calm waterway and the setting sun, creating a picturesque evening view.

Guesthouse in Long Bay Hills

4.99 out of 5 average rating, 175 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Top guest favorite

A modern kitchen features stainless steel appliances, including a refrigerator and stove. A central island with a marble countertop is complemented by three bar stools. Brightly colored decorative flowers are arranged on the counter, accentuating the contemporary design.

Condo in Grace Bay

4.99 out of 5 average rating, 151 reviews

1 Bedroom Luxury Grace Bay Condo in Best Location

The perfect location, and only a 5 minute walk to world famous Grace Bay Beach! Located in the heart of Grace Bay near Seven Stars Resort and the Ritz Carlton Resort. 5 minute walk to the beach. 2 minute walk to the best grocery store, and 10 minute walk to the best restaurants and shopping on the island. No rental car is needed. This 790 sq. ft. luxury one bedroom, newly built condo (Nov 2020), provides all necessary amenities for your home away from home.

The expansive resort pool area features multiple sections, including a large main pool with a central gazebo. Vibrant palm trees surround the space, enhancing the tropical atmosphere, while sun loungers and umbrellas are positioned nearby for guest relaxation.

Condo in Providenciales

4.92 out of 5 average rating, 243 reviews

★★★★★ Modern Condo | Amazing Pool | On Site Spa

• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance

Top guest favorite

A spacious outdoor terrace is featured, furnished with comfortable seating and lounge chairs. The area is surrounded by swaying palm trees and offers views of the landscape. Sunlight casts gentle shadows across the stone floor, creating a relaxing environment.

Guesthouse in Leeward Settlement

4.97 out of 5 average rating, 114 reviews

"The Nest Cozy Cottage"

“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.

A spacious bedroom is furnished with a comfortable bed featuring a white quilt. A chair and nightstand are positioned beside the bed. The room is bright, highlighted by natural light from the window. A closet is visible through an open door.

Cottage in Leeward Settlement

4.93 out of 5 average rating, 115 reviews

Sandpiper Cottage, minutes from the beach

Kick back and relax in this delightful modern one bedroom cottage in the high end residential gated community of Leeward. Grace Bay Beach, most recently voted “The best in the world” is only a 4 minute walk away! This cozy cottage is perfect for a couple, wanting to relax and have some downtime. Complete with full kitchen, washer/dryer/ BBQ, high speed internet with cable TV and all amenities needed for the perfect getaway.

A thatched-roof gazebo is positioned near the water, surrounded by sandy ground and lush vegetation. Palm trees sway gently, and a calm body of water is visible in the background, reflecting the bright blue sky with fluffy clouds.

Loft in Long Bay Hills

4.88 out of 5 average rating, 177 reviews

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders.

A modern living area is shown, featuring a gray couch with green decorative pillows. A light-colored coffee table is positioned in front of the couch. Two framed pieces of wall art enhance the space. A chair is also visible, contributing to the open layout.

Apartment in Grace Bay

4.82 out of 5 average rating, 167 reviews

Crescent 4 - Grace Bay beach 2 min walk

My place is just a two minute walk to one of the most beautiful beaches in the world, Grace Bay beach. Absolutely great spot to walk to many restaurants, bars, casino, grocery store and shopping centre at Salt Mills. You’ll love my studio because of the neighbourhoods and quiet area. Studio apartment has open concept, only door for the bathroom. Place is good for couples, solo adventurers and business travellers.

An inviting interior space combines a comfortable green sofa with a vibrant orange wall. A queen bed is visible in the background, surrounded by natural light from glass doors. Decorative pillows add color, while a ceiling fan and art piece enhance the cozy atmosphere.

Guesthouse in Leeward Settlement

4.9 out of 5 average rating, 146 reviews

Pelican Cottage -Mins. to the Beach!! Car 4 Rent!

Nestled in the tranquil gated community of Leeward, on the heels of the Grace Bay area and the Grace Bay Beach, most recently ranked as the “The Best Beach in the World!”. The upscale Leeward community is within a 5-8 minute drive to the Grace Bay shopping and restaurant district, with about two dozen businesses, including a large grocery store, banks, liquor store, café, phone company, and bookstore.

Top guest favorite

The image captures the exterior of a cottage at dusk, highlighting a lighthouse-shaped tower with softly illuminated windows. A poolside area is visible, featuring lounge seating and a dining area, all surrounded by white walls and a well-maintained patio space.

4.98 out of 5 average rating, 185 reviews

“The Lighthouse”, Private Pool, Ocean Views, Beach

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Vacation rentals for every style

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Popular amenities for Leeward kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

An aerial view of a modern villa surrounded by lush greenery. The exterior features large glass windows and a private pool, accompanied by sleek lounge chairs on the deck. The open layout invites natural light, showcasing the villa's seamless connection to its outdoor surroundings.

Home in Providenciales

4.96 out of 5 average rating, 345 reviews

Villa Cocuyo Micro Villa with pool

A charming home is surrounded by lush palm trees and vibrant tropical landscaping. The exterior features a combination of stucco walls and a tiled roof under a clear blue sky. A gravel path leads to the entrance, adding to the welcoming ambiance.

Home in Grace Bay

4.92 out of 5 average rating, 116 reviews

Tropical Carabas Villa!

A serene beach scene captures the sun setting over calm waters. Soft sand stretches toward the shoreline, dotted with people enjoying the tranquil atmosphere. Gentle waves lap at the beach, while a few boats can be seen in the distance under a partly cloudy sky.

Home in Grace Bay

4.88 out of 5 average rating, 112 reviews

Gated Villa w Pool. Walk to GraceBay Beach & Shops

A spacious gazebo features a red and white picnic table, providing an ideal spot for relaxation. The surrounding views showcase the tranquil waters of Chalk Sound and lush greenery, creating a serene environment for enjoying nature.

Home in Providenciales

4.76 out of 5 average rating, 124 reviews

Beach Cottage with Amazing Chalk Sound Views!

A bright living area showcases white furniture accented with cushions in soothing shades of blue and grey. An elegant glass coffee table sits in the center, reflecting natural light from expansive windows, while a glimpse of the kitchen and dining area can be seen in the background.

Home in Islands

4.99 out of 5 average rating, 110 reviews

The Sapphire Villa. Tropical Oasis. Make memories

The living room features a neutral color palette with light wood accents and high ceilings. Two sets of sliding glass doors provide access to the wrap-around balcony. Seating options include a leather sofa and two wooden chairs beside a glass coffee table, with a television mounted on a console.

Home in Providenciales

4.91 out of 5 average rating, 108 reviews

Sea La Vie - Beachside 2 bdr Unit #4, Ocean views

An outdoor decking area features four woven loungers arranged around a central table. Lush greenery surrounds the space, and a clear blue sky is visible above, enhancing the tranquil atmosphere. A glimpse of a swimming pool can be seen in the background.

Home in Providenciales

4.96 out of 5 average rating, 116 reviews

Sunny Paradise Long Bay

A view from a shaded terrace showcases lush green vegetation and tall trees against the backdrop of a vibrant blue ocean. The wooden railing highlights the outdoor space, framing the expansive vista of the coastline and distant structures in the background.

Home in Providenciales and West Caicos

4.85 out of 5 average rating, 124 reviews

Paradise Villa #4, (Studio)

Kid-friendly apartment rentals

A bright living area is furnished with a light-colored sofa and two teal chairs, offering views through large glass doors. Artwork adorns the white walls, and the inviting outdoor pool is visible beyond a spacious terrace, enhancing the room's airy feel.

Apartment in Venetian Road Settlement

4.94 out of 5 average rating, 113 reviews

OCEAN ORCHID

Aerial view of the property showcases a lush landscape with a pool surrounded by tropical greenery. The two-story condominium complex features balconies adorned with greenery. The serene blue water of the pool contrasts with the vibrant palm trees and well-maintained gardens.

Apartment in Grace Bay

4.85 out of 5 average rating, 117 reviews

Elegant Penthouse in the Heart of Grace Bay

A freshwater pool is set within a sunlit area, bordered by vibrant bougainvillea flowers. A shaded gazebo is visible in the background, furnished for relaxation. The surrounding landscape features greenery, enhancing the tranquil environment near the water.

Apartment in Cooper Jack Bay Settlement

4.93 out of 5 average rating, 138 reviews

Poco Villa

A spacious bed with a light-colored duvet and decorative floral runner is positioned against a neutral wall. Two bedside lamps illuminate the area, and a large closet with white doors is visible in the background. A textured rug lies underneath the bed.

Apartment in Juba Sound

4.96 out of 5 average rating, 113 reviews

Beautiful Studio SMALL CAR Inclusive

A serene view of the private Infiniti pool reflects the surrounding turquoise waters. Two lounge chairs are positioned on a textured surface, framed by a draped canopy that offers shade and relaxation. The tranquil landscape of Chalk Sound completes the peaceful atmosphere.

Apartment in Providenciales

4.9 out of 5 average rating, 187 reviews

Beautiful Sunset Villa with Infiniti Pool

Top guest favorite

A panoramic view captures the ocean on the horizon, framed by swaying palm trees. The foreground features a spacious terrace with blue umbrellas providing shade. Below, a row of white-roofed buildings is nestled among lush greenery, enhancing the serene coastal atmosphere.

Apartment in Providenciales and West Caicos

4.94 out of 5 average rating, 195 reviews

☀️🏖 Modern Luxury Ocean View Studio Suite 🏝☀️

A well-lit studio is featured, showcasing a spacious sleeping area with a bed, and a cozy living space with a sectional sofa adorned with colorful throw pillows. A dining table and kitchenette are visible, equipped with modern appliances and ample natural light from the windows.

Apartment in Long Bay Hills

4.92 out of 5 average rating, 108 reviews

Very Large Studio & Porch, 5 mins Beach, Secluded

A modern living area is furnished with a blue sofa and a light gray chaise lounge featuring button-tufted upholstery. A glass coffee table is positioned in the center, surrounded by plush throw pillows. Soft natural light enters through large glass doors, complemented by elegant lamps beside the sofa.

Apartment in The Bight Settlement

4.96 out of 5 average rating, 25 reviews

Spacious Beach Suite - Minutes from Grace Bay

Kid-friendly condo rentals

Top guest favorite

A view of lush green vegetation and palm trees is presented from a balcony, overlooking a turquoise pool and surrounding resort area. A clear blue sky complements the tranquil scene.

Condo in Turtle Cove

4.93 out of 5 average rating, 116 reviews

Allies Rest - Seaflowers townhome

A spacious living area is equipped with a comfortable sofa adorned with patterned cushions. A wooden coffee table sits in the center, while a large flat-screen TV is mounted on the wall. Floor-to-ceiling glass doors lead to a balcony with ocean views, framed by light blue drapes.

Condo in Turtle Cove

4.9 out of 5 average rating, 109 reviews

1 BD, 1.5 Bathrooms, RENTAL CAR INCLUDED

Two comfortable lounge chairs with blue cushions are positioned beneath a large blue umbrella on a spacious terrace. The backdrop features views of the ocean and lush greenery, while vibrant pots of flowers add a touch of color to the setting.

Condo in Providenciales

4.95 out of 5 average rating, 193 reviews

Amazing Ocean views -Modern Condo -Balcony - Pool

A covered balcony offers outdoor seating with two armchairs and a coffee table. Lush greenery surrounds the area, and a pool can be seen in the background. The tiled floor complements the natural elements of the space.

Condo in Providenciales

4.88 out of 5 average rating, 140 reviews

*Balcony View* Renovated Modern Studio C202

A serene view of Turtle Cove Marina features glistening blue waters framed by lush green palm trees. Several boats are docked in the marina, and a clear sky stretches above, creating a peaceful coastal atmosphere.

Condo in Providenciales and West Caicos

4.87 out of 5 average rating, 444 reviews

🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞

A serene beach scene features soft white sand leading to calm waters, with lounge chairs placed under umbrellas. The tranquil sky displays a gradient of pastel colors as the sun sets, illuminating the nearby condominium and surrounding palm trees.

Condo in Wheeland Settlement

4.95 out of 5 average rating, 125 reviews

Couple’s Retreat - ocean view, pool and hot tub!

A panoramic view captures the vibrant blue sea meeting the sky, with soft clouds scattered above. The foreground reveals lush greenery, complemented by the colorful rooftops of nearby buildings, showcasing the natural beauty of the area.

Condo in Providenciales

4.86 out of 5 average rating, 124 reviews

Amazing GraceBay Views, Pools,Location PH Studio

A serene pool area is surrounded by lush tropical greenery and palm trees. Vibrant flowers adorn the edges of the pool, while lounge chairs and umbrellas provide shaded seating. The sunny sky reflects on the calm water, creating a tranquil atmosphere.

Condo in Turtle Cove

4.98 out of 5 average rating, 110 reviews

Shore to Please - Large Studio Condo with Patio

Quick stats about vacation rentals that are kid-friendly in Leeward

Total rentals
30 properties
Nightly prices starting at
G$27,168 GYD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore