Family-friendly holiday rentals in Wellington

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, 114 reviews

Wellington Guest Suite

Wellington guest suite for the winter horse show season. Private entrance and it's separate from the rest of the home. Shared driveway parking. Quiet neighborhood. Close to restaurants, grocery stores, mall, show jumping, dressage, and polo attractions for your convenience. Rental to one/two person(s)only. No smoking. Small pets only. King size bed, full bath, walk-in closet, sofa, dinette table, TV, (Wifi access), kitchenette with fridge, microwave, toaster and coffee maker. No washer & dryer

KitchenIndoor spacesDecor

Superhost

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

4.81 out of 5 average rating, 102 reviews

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. 🌴🏊‍♂️✨

KitchenFamilyNearby

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, 319 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.

FamilyIndoor spacesSleep quality

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, 132 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!

KitchenFamilyPool

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.

4.99 out of 5 average rating, 152 reviews

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

Indoor spacesKitchenAmenities

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.

4.77 out of 5 average rating, 106 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

FamilyKitchenGrill

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.

4.82 out of 5 average rating, 158 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.

Indoor spacesKitchenAmenities

4.96 out of 5 average rating, 68 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.

Indoor spacesFamilyBathroom

4.97 out of 5 average rating, 63 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

KitchenFamilyGrill

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, 108 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.

KitchenIndoor spacesComfort

Guest house in West Palm Beach

A modern studio room features a spacious bed with a white quilted coverlet and a dark green throw. A stylish mirror and wall-mounted television are positioned above a white dresser. Green accent decor adds a touch of nature, complementing the clean, neutral color palette.

4.97 out of 5 average rating, 153 reviews

Charming studio with All the Essentials

Welcome to your peaceful West Palm Beach retreat! This cozy, modern studio is nestled in a quiet, safe neighborhood, perfect for relaxing after a day of exploring. Whether you’re here for work or play, you’ll enjoy a comfortable, clean space thoughtfully designed to help you feel right at home. Unwind in a peaceful setting with all the essentials you need—ideal for solo travelers, couples, or anyone seeking a calm, cozy getaway in a great location.

Indoor spacesKitchenBeach

4.96 out of 5 average rating, 24 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!

KitchenFamilyBack garden

Popular amenities for Wellington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.82 out of 5 average rating, 65 reviews

Pool Home in Wellington

KitchenIndoor spacesCheck-in

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, 183 reviews

Raven Haus: Curated 2 Bedroom Guest House w/Pool

KitchenIndoor spacesLayout

5 out of 5 average rating, 21 reviews

Paradise in Equestrian Walk

KitchenFamilyPool

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, 163 reviews

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

Indoor spacesKitchenQuiet

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.

4.98 out of 5 average rating, 54 reviews

Saddle Up in Style

KitchenFamilyLong stay

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, 291 reviews

#1 Lake Osborne Tropical Pool Oasis HEATED POOL

FamilyKitchenDecor

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.

4.78 out of 5 average rating, 193 reviews

Magical villa -Private pool-spa & garden

KitchenFamilyComfort

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.

4.97 out of 5 average rating, 534 reviews

Key West Style Suite with Pool/Spa

Indoor spacesFamilyParking

Family- and pet-friendly home rentals

Superhost

Villa in Wellington

4.8 out of 5 average rating, 10 reviews

Modern 3BR Villa + Pool and Patio near WEF

FamilyNearbyCleanliness

4.94 out of 5 average rating, 95 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

Indoor spacesKitchenNearby

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, 56 reviews

Equestrian Villa w/Pool & Volleyball, Near Polo

KitchenFamilyBathroom

A single-story home is displayed with a large, shaded front yard, featuring a prominent tree. The roof is finished in neutral tones, complemented by a spacious driveway leading to a two-car garage. Surrounding greenery adds to the tranquil setting.

4.97 out of 5 average rating, 61 reviews

Comfy House in Nice Neighborhood

KitchenFamilyPets

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 out of 5 average rating, 27 reviews

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

KitchenIndoor spacesLocation

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, 27 reviews

Beautiful 4bed/4bath Home in Wellington

KitchenFamilyHot tub

4.97 out of 5 average rating, 206 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.

Home in Royal Palm Beach

Priviliged Location/ Direct access to Nature Park

FamilyIndoor spacesTV

Guest suite in The Acreage

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, 163 reviews

Private, spacious and cozy guest suite

KitchenFamilyCheckout

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 27 reviews

A spacious living area features stylish furnishings, including a comfortable couch and modern chairs. A large television is mounted on the wall opposite. Light streams through expansive sliding glass doors that lead to a private patio, with lush greenery visible outside.

Flat in Wellington

Wellington Polo Club Retreat | St. Andrews

KitchenIndoor spacesValue

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

FamilyIndoor spacesGrill

4.99 out of 5 average rating, 143 reviews

Home in Flamingo Park

Luxe Casa • Stunning Pool • Near Beach & Downtown

FamilyIndoor spacesOutdoor spaces

4.88 out of 5 average rating, 135 reviews

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.

Home in Royal Palm Beach

Royal Palm Oasis

Indoor spacesFamilyBeach

5 out of 5 average rating, 16 reviews

Cabin in West Palm Beach

Charming Rustic Log Cabin with Pool & Farm Animals

Indoor spacesFamilyAmenities

Tiny home in West Palm Beach

A modern container home is highlighted, featuring a sleek wooden facade and large glass doors. A stone pathway leads to the entrance, surrounded by lush green grass. The outdoor area includes a small deck nearby, offering additional space for relaxation.

4.93 out of 5 average rating, 108 reviews

BoxHaus Modern tiny home in the heart of WPB

Indoor spacesKitchenValue

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.

4.89 out of 5 average rating, 55 reviews

Equestrian Pool Home and Spa - Golf

Indoor spacesKitchenHospitality