Family-friendly holiday rentals in Wellington

4.82 out of 5 average rating, 104 reviews

An inviting pool area is enclosed by a screened patio, allowing clear views of the expansive green space beyond. The shimmering water reflects sunlight, and several lounge chairs are positioned along the side, creating a relaxing space for enjoyment.

Villa in Wellington

Wellington Pool Retreat | 4BR/2.5BA

Welcome to Wellington Pool Retreat! 🏡☀️ This spacious 2,500 sq. ft. home in the desirable Wiltshire Village community features 4 bedrooms, 2.5 bathrooms, and a private heated pool. Enjoy the fully screened patio with a new outdoor kitchenette, 4K TV, lounge seating, and updated lighting—perfect for relaxing or entertaining. Backing to a large tree-lined green space, the home offers exceptional privacy while being conveniently located near shopping, dining, and Wellington attractions. 🌴🏊‍♂️✨

A spacious pool area features a heated saltwater pool surrounded by tropical foliage and sun loungers. An outdoor dining area with a table and chairs invites relaxation, while the open concept living area showcases bright decor and ample natural light from large windows.

4.8 out of 5 average rating, 324 reviews

Paradise Pool Cottage in Wellington/WPB/Polo

Beautifully appointed resort style 2 bed, 1 bath cottage. Located 5 minutes away from the Equestrian and Polo Grounds and 20 minutes from stunning South Florida beaches. This boutique style spa home is perfect for a laid back vacation style trip to the WEF, a perfect base for exploring the Palm Beaches, an overnight concert trip to the Amphitheater and Sunfest. The tropical patio, heated saltwater pool and hot tub are ideal for relaxing around, with sun loungers, outdoor eating area and grill.

An open-concept living space features a comfortable seating area with dark sofas and decorative pillows. A wooden dining table is set for several guests. Ceiling fans provide airflow, while large windows allow natural light to brighten the room. A modern kitchen is visible in the background.

4.96 out of 5 average rating, 166 reviews

Beautiful 3-bedroom, 2-bathrooms house with pool

Welcome to La Casa De Las Dos Palmas, located in a friendly West Palm Beach neighborhood. PBI Airport 5 min away, beaches and downtown 10 min, Supermarkets 4 min. Each room comes with Roku TV. Fully furnished, including washer and dryer, gas grill, coffee maker, dishwasher, toaster, stove with air fryer, WiFi, dimmable lights, and more. The property has an independent apartment with it’s own entrance for two people maximum. It’s completely separate from the house. Backyard and pool are shared.

A screened-in patio highlights a clear blue pool surrounded by tropical landscaping. Lounge chairs are positioned nearby, and a child safety fence secures the area. The structure provides an inviting environment for relaxation with abundant natural light filtering through the screens.

4.99 out of 5 average rating, 133 reviews

*5 STAR* Family Friendly 3 Bed Home w. Heated Pool

Our Wellington home is perfect for equestrians, families or those just looking for home away from home while in the area. We don't use the word home lightly - this is our residence when we are in Wellington, so no detail has been overlooked. Complete with comfortable floor plan with renovated kitchen & baths. Details include hi-speed WIFI, smart-home, new washer/dryer and screened patio area w. kid fence - perfect for relaxing poolside, both day & night. Amenities for ALL kid ages from 0 - 18!

A screened-in pool area features a spacious blue pool with a built-in spa, surrounded by a large patio. Comfortable lounge chairs are positioned for relaxation. Sunlight streams through the mesh enclosure, creating an inviting atmosphere for swimming and enjoying the outdoors.

4.78 out of 5 average rating, 108 reviews

Cozy Home with Pool & Spa (Heated) in Wellington

This home is set up to provide all the comforts you need. This beautiful property is located minutes from the equestrian centers. There is a screened in pool area allowing you to enjoy the pool without needing to worry about any Florida bugs. The spa is perfect for relaxing. All the bedrooms are comfy, and the master provides comfort and plenty of space for quiet time if needed. There are also two living room areas, and plenty of seating set up so memories and family time will be easy to have

Guest suite in Wellington

A spacious room features a modern white bed with a colorful blanket. A work desk with a chair is visible, alongside dark wooden nightstands. A large mirror reflects the area, while artwork adorns one wall. Natural light enters through a nearby window.

Amazing One Bedroom Studio 2.5 miles from WEF

Furnished large room with a completely private entrance and it's own designated parking on the driveway. The Studio is very close to WEF and The Polo Club in the heart of Wellington... LOCATION, LOCATION, LOCATION, it is within a Great neighborhood, quiet, clean and safe. This is the perfect place to stay while enjoying the beautiful equestrian season in Wellington or for a business person/couple that works remotely, the internet is fast and the studio has a comfortable work desk and chair.

4.88 out of 5 average rating, 214 reviews

A bright, open kitchen features modern appliances and a central island with bar seats. The dining area includes a table with chairs, positioned adjacent to a large sliding glass door that offers views of the outdoor space and allows natural light to flood the room.

4.97 out of 5 average rating, 208 reviews

Priviliged Location/ Direct access to Nature Park

MODERN 3BEDS/2 BATHS **PRIVILIGED LOCATION WITH DIRECT ACCESS TO "COMMONS PARK" 19 ACRESS PARK, LAKE, KAYAKING & FISHING RIGHT IN OUR BACKYARD** Near Equestrian Wellington. Easily accommodates up to 8 guests. Pet friendly (max 2 pets) Spacious house display. 20-30 minutes from the beach. 5 -10 minutes from shopping centers, restaurants, gas station, supermarkets. 20 mins from Palm Beach Intl Airport Super quiet and safe neighborhood. COME ENJOY!! *** NO PARTIES ALLOWED AT THIS PROPERTY

Home in Loxahatchee Groves

Royal Getaway

Royal Palm Getaway Escape to this spacious and private single-story home in the heart of Royal Palm Beach. Enjoy a relaxing getaway. Located near Commons Park, equestrian activities, golf courses, shopping, restaurants, Wellington Mall, downtown, and Palm Beach beaches. Commons Park is 5 minutes away, and Palm Beach International Airport is 20 minutes away. ~4 Bedrooms ~2 Bathrooms | ~Private Pool | Screened Patio | BBQ Grill ~Quiet Neighborhood Please note: The pool is not heated.

4.91 out of 5 average rating, 290 reviews

A spacious outdoor patio features a shimmering pool surrounded by lounge chairs and a relaxing hot tub. Colorful pool floats are positioned in the water, while a shaded seating area offers comfortable furnishings. Lush greenery and a clear sky enhance the serene atmosphere.

4.95 out of 5 average rating, 64 reviews

Saddle Up in Style

Escape to this stylish Wellington retreat in the heart of horse country—minutes from stables, shows, and races. Enjoy a chef’s kitchen, and spacious outdoor dining perfect for family meals. Unwind with ping pong, board games, or a cozy movie night. For those working on vacation (seriously, why?), there’s a desk and monitor ready to go. We won’t judge—just don’t forget to hit the pool after those emails. Whether you're here for the equestrian scene or just to relax, this home has it all.

A wooden deck is surrounded by lush greenery, with two lounge chairs positioned for relaxation. A hammock is visible nearby, offering a cozy spot for lounging. A shaded area is provided by a cloth canopy, enhancing the outdoor space's comfort.

4.83 out of 5 average rating, 165 reviews

1 Paradize for equestrian lovers Sugar Pond Manor

This is a warm and guest friendly house . We did our best for you to feel at home and enjoy your stay.In sunshine state of Florida you can enjoy our private pool and BBQ. Is great location for friends or families. In only 10-15 min you can visit zoo,water parks, great restaurants, shopping malls,golf clubs,opera or drama theatre. This is could be a romantic get a way or family trip there a lot of fun activities for any purpose. We love staying in our house and we hope you will too.

5.0 out of 5 average rating, 21 reviews

Paradise in Equestrian Walk

Welcome to your dream home in the heart of Polo Wellington! spacious residence features 4 bedrooms, 5 beds, and 3 full bathrooms, perfect for families or entertaining guests. Enjoy the luxurious saltwater , heated swimming pool and unwind with entertainment options like a billiard table and foosball table. With everything you need close by, this home truly offers best of convenience and comfort. The exclusive Equestrian Walk neighborhood, where peace, quiet, and safety come together.

The exterior of the home is viewed from a distance, showcasing a spacious driveway leading to a two-car garage. Lush greenery surrounds the property, with palm trees and landscaped gardens enhancing the tranquil environment.

4.94 out of 5 average rating, 111 reviews

Entire Home With Luxury Pool and Heated Spa

Escape to a luxury 3-bed, 2-bath South Florida oasis in the heart of Wellington. This private home comfortably fits 6 guests and features a large swimming pool, hot tub, two living rooms, and a fully equipped kitchen. Perfectly located, you can walk to local shops, diverse restaurants, and a movie theater. Enjoy the ultimate relaxing getaway with exclusive access to your own private paradise, complete with a BBQ grill and a two-car garage for your convenience.

Popular amenities for Wellington family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A vibrant outdoor space features a large palm tree amidst well-manicured grass and tropical plants. Cozy seating with string lights creates a relaxing evening ambiance. Pathway stones lead toward a putting green area, enhancing the backyard's recreational appeal.

4.96 out of 5 average rating, 166 reviews

“The Palms” Tropical Oasis|Beach|Scuba|Downtown

4.8 out of 5 average rating, 168 reviews

A serene backyard scene features two lounge chairs positioned near a sparkling pool. Soft lighting surrounds the area, casting a warm glow on the patio and nearby seating. Lush greenery and a clear sky enhance the tranquil atmosphere.

Home in Lake Worth

Canal-1 3/2 Beach Style House with Heated Pool

4.85 out of 5 average rating, 293 reviews

A spacious heated pool glistens under bright sunlight, surrounded by lush tropical plants. Comfortable lounge chairs are positioned along the deck, with two decorative planters adding a touch of elegance. A basketball hoop stands ready for play, creating an inviting outdoor space.

Home in Lake Worth

#1 Lake Osborne Tropical Pool Oasis HEATED POOL

A spacious pool area is presented, featuring a rectangular pool surrounded by lounge chairs and tropical landscaping. A thatched-roof gazebo offers a shaded seating area in the background, while a large umbrella provides additional shade near the pool. The bright blue sky enhances the inviting atmosphere.

4.99 out of 5 average rating, 153 reviews

Jungle Oasis with Heated Pool, Tiki Hut & Hot Tub

4.84 out of 5 average rating, 276 reviews

A hot tub is positioned alongside a tranquil body of water, with clear blue water bubbling within. Two glasses are set beside a bottle of wine on the edge. Lush greenery and a fence frame the background, contributing to a serene outdoor environment.

Home in Boynton Beach

Beautiful house with jacuzzi and pool table!

The mid-century ranch home features a vibrant blue exterior, surrounded by tropical landscaping. A well-maintained front yard showcases lush greenery and flowering plants. A driveway leads to a single-car garage, with palm trees providing shade along the property. Clear skies enhance the inviting curb appeal.

4.9 out of 5 average rating, 104 reviews

3 bedroom Casa Azul in Historic Northwood Hills

A screened outdoor area showcases a sparkling swimming pool with a gentle curve, surrounded by a spacious deck. Lounge chairs are positioned nearby, and a shaded seating area is visible within the enclosure, inviting relaxation on sunny days.

5.0 out of 5 average rating, 27 reviews

Beautiful 4bed/4bath Home in Wellington

An inviting indoor space features two cozy seating areas with light-colored wicker chairs and a small table. Natural light filters through large screened windows, revealing a view of the pool and lush greenery. A ceiling fan offers a cooling touch in this serene atmosphere.

4.81 out of 5 average rating, 67 reviews

Pool Home in Wellington

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 159 reviews

Modern Living in Royal Palm Beach

Guest suite in Wellington

A spacious living area showcases a comfortable brown sofa facing a wall-mounted TV. A light-colored coffee table is placed on a patterned rug. Kitchen amenities, including a large refrigerator and microwave, are visible along one wall under bright, natural light from two windows.

Wellington Guest Suite

4.97 out of 5 average rating, 115 reviews

4.95 out of 5 average rating, 103 reviews

An outdoor pool area is enclosed with a black fence, featuring a spacious swimming pool with clear blue water. A patio is visible alongside the pool, bordered by well-maintained grass and trees in the background, inviting relaxation and leisure.

Home in Boynton Beach

4/3.5 SF with Pool, Near Delray, Boca & Wellington

Guest suite in Royal Palm Beach

A charming outdoor area surrounded by lush greenery features a cozy seating arrangement under a wooden pergola. Potted plants add a touch of nature, and a private entrance is indicated by a glass door, inviting light into the vibrant villa suite.

Adorable | Private | Self Check-in Suite

4.86 out of 5 average rating, 261 reviews

Home in Palm Springs Village

A spacious living area is highlighted by a cozy sectional sofa and a round coffee table. Natural light fills the room through large windows, while a dining area with a modern table and chairs is visible in the background. Contemporary artwork decorates the walls.

Modern & Luxurious Villa in West Palm Beach

4.92 out of 5 average rating, 136 reviews

4.98 out of 5 average rating, 108 reviews

A private tropical backyard features a heated salt system pool surrounded by lush greenery. Loungers are positioned beside the pool, and a red umbrella provides shade over a designated seating area. The home’s windows offer views into the tranquil outdoor space.

Home in Boynton Beach

Jungle Heated Salt Pool, Private, Near Beach

4.83 out of 5 average rating, 12 reviews

Villa in Wellington

Modern 3BR/2BA Villa + Pool near WEF and POLO

A two-story retreat is shown from the front, featuring a clay tile roof and gentle landscaping. Tropical plants and palm trees frame the entrance, while a spacious driveway leads to a double garage. A welcoming atmosphere is created by large windows allowing natural light.

5.0 out of 5 average rating, 29 reviews

Sunny Oasis| Pool| Top Location |Big Patio| 4 BR

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 157 reviews

A vibrant pink pool float with the text 'OUT OF OFFICE' is placed in the clear blue water of a private swimming pool. Additional pool floats in various colors are visible, creating a playful atmosphere. Lush greenery surrounds the pool area.

Home in Lake Worth

Tranquil Vibes ~ Pet Friendly Private Pool Home

Home in Palm Springs Village

The Royal Gourmet charcoal grill is positioned near the sparkling pool, with the sturdy grill surface facing the viewer. A blue soccer goal stands in the background, framed by lush green foliage, providing a vibrant outdoor setting.

4BR Oasis w/Heated Pool, Near I-95 + Free Coffee!

4.89 out of 5 average rating, 181 reviews

5.0 out of 5 average rating, 51 reviews

West Palm Beach Heated-Pool House

A private screened-in pool area is showcased, featuring a spa and a spacious deck. Soft lighting highlights the water's blue hues, creating a serene environment. Comfortable seating is available, surrounded by lush greenery, offering an inviting space for relaxation.

4.88 out of 5 average rating, 58 reviews

Equestrian Pool Home and Spa - Golf

4.96 out of 5 average rating, 24 reviews

Newly Renovated House with Luxury Pool

4.96 out of 5 average rating, 23 reviews

Cozy Summerhouse with Pool 3br

An aerial view showcases the home's layout, featuring a spacious backyard with a private pool surrounded by patio space. Lush green grass and palm trees frame the outdoor area, providing a relaxed environment. The house features a modern roof and is situated in a tranquil neighborhood.

4.96 out of 5 average rating, 78 reviews

5BR Wellington Equestrian Retreat, Pool & Games