Family-friendly holiday rentals in Wellington

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.

4.79 out of 5 average rating, 315 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.

Guest house in Lake Worth

An open studio layout showcases a comfortable sleeping area with a plush queen-size bed. A fully equipped kitchen featuring stainless steel appliances is visible, alongside a dining table and chairs. A cozy seating area includes a stylish chair, while natural light brightens the space.

4.99 out of 5 average rating, 214 reviews

Upscale Private Wellington Guest House | Near WEF

Private upscale guest house in the heart of Wellington, perfect for equestrian events, seasonal stays, business travel, or relaxing getaways. Features a fully equipped kitchen, renovated bathroom, washer and dryer, comfortable sleeping area, WiFi, TV, and private patio in a quiet upscale neighborhood. Minutes to WEF, polo grounds, beaches, restaurants, shopping, and golf. Enjoy privacy, comfort, and convenience in one of Wellington’s most desirable locations. Ideal for short or extended stays.

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, 129 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 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, 198 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

4.85 out of 5 average rating, 118 reviews

An unheated swimming pool with clear blue water is surrounded by a fenced patio. Lush palm trees frame the area, providing a tropical feel. The sunny sky enhances the serene atmosphere of the backyard space, with green grass visible in the background.

Bungalow in Wellington

Cozy waterfront king-bed bungalow in Wellington

Spacious 2150sqf waterfront pool house! Three charming French doors are leading from the master bedroom, dining and living rooms to a serene back patio with a view of the pool and waterfront. Minutes from the IPC, Equestrian centers, the Green Mall, and many restaurants and shops. 20 minutes from the ocean. Bring the whole family to this peaceful place with lots of room for fun and relaxation. For the fans of fishing, there is a rod with accessories in the garage for you to use and enjoy.

A spacious living room features a large sectional couch adorned with yellow and white accent pillows. A round mirror and decorative shelves with plants are mounted on the wall. A glass sliding door opens to a patio area, allowing natural light to fill the room.

4.94 out of 5 average rating, 142 reviews

Modern Living in Royal Palm Beach

If you're looking for a home to relax in while enjoying the many amenities of WPB then look no further. This beautifully upgraded three bedroom, two bath home boasts lots of natural light and plenty of space for all of your guests. Equipped with a great backyard space, screened-in patio, and ample parking, this place is perfect for everyone to unwind. Minutes away from shopping areas, restaurants, beaches, golf courses, downtown attractions, and PBI, you'll have all you want and need!

A modern living space features a large sectional sofa in a neutral tone, complemented by a stylish glass coffee table with decorative sculptures. A dining area is visible with upholstered chairs and a sleek table, set against a backdrop of light wood flooring and contemporary artwork.

4.97 out of 5 average rating, 38 reviews

Equestrian Home

Your family will be close to everything when you stay at this centrally-located home. A charming 3 bedroom, 2 baths, 1 car garage fully remodeled in the heart of Wellington. Everything inside is brand new, beds, furniture, linens ready to welcome you. Ample screened patio to relax in the afternoon, with a gas grill. Conveniently located within walking distance to shopping, dining, and just a hand full of minutes to all equestrian venues. Short ride to Lion Country Safari.

4.95 out of 5 average rating, 59 reviews

A contemporary living area features a spacious white sectional sofa adorned with colorful accent pillows. A sleek coffee table sits nearby, showcasing a decorative plant. A modern kitchen with white cabinetry and barstools is visible, complemented by warm lighting from pendant fixtures.

Villa in Wellington

Alluring Luxury Oasis: Modern Comfort & Relaxation

Escape to your private haven in a prime location in the heart of Wellington in at Villa Azalea, a stunning villa nestled within the peaceful Sugar Pond Manor community. This freshly designed retreat is the perfect home base for exploring Wellington's equestrian scene, vibrant culture, and natural beauty. Experience the finer things as you relax in a stylish space with a fully equipped kitchen, comfortable living area, and in-unit washer/dryer for ultimate convenience.

5 out of 5 average rating, 31 reviews

Elegant & Glamorous way private pool with heater

Welcome to this spacious and stylish home designed for guests who enjoy comfort, luxury, and beautiful surroundings. This large property features a sophisticated blend of modern elegance and glamorous details, creating the perfect atmosphere for unforgettable family vacations. open living spaces with high-end décor, comfortable seating, and a warm, inviting ambiance. The home offers multiple bedrooms, ideal for large families or groups who want to relax together

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.

4.86 out of 5 average rating, 235 reviews

Adorable | Private | Self Check-in Suite

This is a peaceful and centrally- located place. It is a one bedroom villa suite, with a private side entrance on the north end of the residence. Located in an A rated community. Perfect for any traveler, or Polo club equestrians, sunny- beach goers, or avid year round golfers, we are located only 8 miles away from the PalmBeach Golf & Polo Club, 12 miles away from the PBI airport, 12 miles from Down town WPB, and 14 miles away from our scenic Midtown- Beach!

4.95 out of 5 average rating, 19 reviews

Newly Renovated House with Luxury Pool

Villa Matilda is a brand-new luxury modern 2-bedroom, 1-bath home perfect for couples, families, or equestrian guests. Enjoy a bright open living space, fully equipped kitchen, cozy bedrooms, and a sparkling private pool. Relax in the serene backyard, sip your morning coffee, or take advantage of nearby riding trails and stables. Stylish, comfortable, and private — the perfect Florida retreat for sun, relaxation, and adventure!

A spacious living area features a large sectional sofa facing a wooden coffee table with a decorative plant. Light-colored walls enhance the ambiance, while a stylish ceiling fan and a chandelier provide illumination. Dining space with a dark wood table is visible through the open layout.

4.94 out of 5 average rating, 64 reviews

Cheerful 3 Bedroom Home less than a mile to WEF

Discover your cheerful 3-bedroom Wellington home, perfect for families! Comfortably sleeps 6. Located less than a mile from the Winter Equestrian Festival (WEF), this cozy house features a fully equipped kitchen, a private fenced backyard, and a separate den for relaxation. Enjoy the convenience of being in the heart of the action while having a peaceful retreat to call your own. Free garage parking included.

Popular amenities for Wellington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest house in Downtown West Palm Beach

A charming exterior of a black wooden home is framed by lush green palm trees and shrubs. A stone pathway leads to the front entrance, with decorative plants positioned along the garden beds. Large windows invite natural light into the space.

4.98 out of 5 average rating, 174 reviews

Raven Haus: Curated 2 Bedroom Guest House w/Pool

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.

4.81 out of 5 average rating, 149 reviews

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

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.

4.85 out of 5 average rating, 284 reviews

#1 Lake Osborne Tropical Pool Oasis HEATED POOL

A tranquil pool area is surrounded by lush palm trees and a vibrant blue patio. Lounge chairs are positioned along the water's edge, while a dining table with yellow chairs offers a sunny spot for meals. An inviting hot tub is situated nearby, enhancing the serene environment.

4.77 out of 5 average rating, 187 reviews

Magical villa -Private pool-spa & garden

4.83 out of 5 average rating, 240 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!

4.89 out of 5 average rating, 120 reviews

A serene backyard offers a heated pool reflecting the vibrant greenery of palm trees. Comfortable loungers are positioned to one side, and a dining area is set under a spacious covered patio, providing an inviting space for relaxation and outdoor gatherings.

Home in Northwood Shores

Tropical Private Hideaway 3 BD-3 BATH

Guest house in Flamingo Park

A bright bedroom features a spacious bed with a textured white cover. Soft blue pillows are arranged neatly, and a cozy chair is placed beside a vintage-style trunk. Natural light enters through two large windows, complemented by light green blinds, creating an inviting atmosphere.

4.98 out of 5 average rating, 512 reviews

Key West Style Suite with Pool/Spa

The outdoor space features a well-manicured lawn with a putting green, framed by lush greenery and palm trees. Soft lighting enhances the atmosphere as the sunset casts a warm glow over the two-story home, creating a welcoming environment for outdoor activities.

4.86 out of 5 average rating, 138 reviews

Drift Inn- Lakefront! Outdoor Bar, Golf, sleeps 14

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 150 reviews

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.

Home in West Palm Beach

Beautiful 3-bedroom, 2-bathrooms house with pool

Guest suite in West Palm Beach

A well-lit bedroom features a queen-size bed with white linens and a decorative throw. A mirrored closet and a modern desk with a chair are visible. Soft curtains frame a window, contributing to the room's bright and airy ambiance.

4.97 out of 5 average rating, 233 reviews

Private Equestrian Retreat Suite

A spacious screened-in dining area features a wooden table surrounded by six chairs. Above, a ceiling fan offers airflow, and natural light filters in through the mesh screens. The pool is visible in the background, bordered by green landscaping and a wooden fence.

4.96 out of 5 average rating, 54 reviews

4 BR Equestrian Pool Home, Volleyball on 2 Acres

Camper van/Motorhome in Wellington

5 out of 5 average rating, 12 reviews

Quiet Retreat

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.

5 out of 5 average rating, 112 reviews

Wellington Guest Suite

4.93 out of 5 average rating, 114 reviews

A welcoming living area features a soft grey sofa adorned with a textured blanket and decorative cushions. Two coastal-themed prints hang above a wooden coffee table that holds various items. Natural light washes through a nearby window, complementing the light, airy decor.

Home in Poinciana Park

Cozy 3BR/2BA West Palm Beach Home w/Private Pool

A spacious residence is set against a blue sky, framed by lush landscaping and a manicured lawn. The architecture features a prominent entryway with elegant columns and a tiled roof. Palm trees and various shrubs enhance the surrounding greenery.

5 out of 5 average rating, 24 reviews

Beautiful 4bed/4bath Home in Wellington

Guest suite in West Palm Beach

A spacious bedroom features a queen-size bed dressed in white linens with gray accents. A large dresser and nightstands flank the bed, complemented by lamps on each side. Natural light enters through sheer curtains, and decorative wall art adds a subtle touch.

4.96 out of 5 average rating, 159 reviews

Private, spacious and cozy guest suite

Family-friendly home rentals with a pool

4.8 out of 5 average rating, 10 reviews

Villa in Wellington

Modern 3BR Villa + Pool and Patio Near WEF

A heated pool is surrounded by tall palm trees and lush greenery. A pink flamingo float rests in the sparkling water, while comfortable lounge chairs are positioned nearby, inviting relaxation in this bright and welcoming outdoor space.

4.98 out of 5 average rating, 96 reviews

Private Palm Oasis Backyard- Pool- King Beds

4.95 out of 5 average rating, 87 reviews

An outdoor tiki area is illuminated under a thatched roof, featuring comfortable seating and a natural wooden table. A swimming pool can be seen in the background, surrounded by lush tropical landscaping. The space is designed for relaxation and enjoyment in a serene setting.

Home in West Palm Beach

Tropical oasis with amazing tiki, pool

5 out of 5 average rating, 33 reviews

West Palm Beach Heated-Pool House

4.99 out of 5 average rating, 127 reviews

Home in Flamingo Park

Luxe Home • Resort-Style Heated Pool • Near Beach

4.89 out of 5 average rating, 53 reviews

Sunny De-Lite / Equestrian Center / Wellington

A spacious bedroom features a large bed with a textured white comforter. A floor lamp and a wooden nightstand are positioned beside the bed. Natural light filters through a covered window, while a decorative plant adds a touch of greenery to the corner.

4.88 out of 5 average rating, 117 reviews

Royal Palm Oasis

A private outdoor space features a heated pool surrounded by a spacious patio. Two blue umbrellas provide shade over seating areas, while tropical vegetation borders the area. The pool's clear water reflects the blue sky, creating a relaxing atmosphere for guests.