luxury houses with pool for rent Wellington, United States

This beautiful home is available for seasonal occupancy! Close proximity to Southern Blvd. and to Wellington's equestrian venues allows for optimal convenience while the 1+ acre lot offers space and privacy. Fully furnished and turn-key with an updated interior and furnishings. Light, bright, and an abundance of space. Rental Terms: Annual: $15,000 Per Month

The perfect place to spend your equestrian season in Wellington. Whether you are looking to relax or entertain by the pool, this is the perfect place to come home to after a busy day. Included for tenants at no extra cost, The Isles features magnificent amenities, including tennis, pickleball, a gym, and a basketball court, just to mention a few. This beautiful home is truly impeccable, thoughtfully designed down to the last detail. The perfect place in Wellington to spend your winter season. Rental Terms: Annual: $10,000 Per Month

Beautiful 4-Bedroom Golf Course Retreat with Pool - Perfect Location! Welcome to this stunning 4-bedroom, 3.5-bath rental home offering style, comfort, and convenience. Tastefully decorated throughout, this home features an updated kitchen with modern finishes, perfect for cooking and entertaining. The spacious primary suite is conveniently located on the main level, while upstairs you'll find three additional bedrooms and a loft, ideal for guests, a home office, or a media space. Step outside to enjoy your private pool overlooking the lush golf course views—a serene backdrop for relaxing afternoons or evening gatherings. Centrally located just minutes from the horse show grounds, shopping, and restaurants, this home combines luxury living with an unbeatable location. Rental Terms: Annual: $8,000 Per Month

Your Perfect Wellington Seasonal Retreat! Enjoy the best of Wellington from this charming 2 bedroom + den/office single-family home in Tree Tops of Wellington. The spacious den offers the flexibility to serve as a third bedroom, making the home ideal for a seasonal stay. The home features a rare oversized side yard, longer driveway, and a quaint patio—perfect for relaxing after a day at the shows. Its unbeatable location puts you a stones throw away to Crunch Fitness, Starbucks, Agliolio's and other great local restaurants, while the Winter Equestrian Festival, Global Dressage, and National Polo Center are all just minutes away. Comfortable, convenient, and perfectly located for the Wellington season—come enjoy everything Wellington has to offer! Rental Terms: Annual: $6,000 Per Month

Charming, well appointed 3/2 home with screened patio available in the gated community of The Isles of Wellington. Find your seasonal stay just minutes away from the newly expanded Winter Equestrian Festival. Fully furnished, tasteful, and cozy decor will ensure your stay is enjoyable and welcomed. Bedrooms feature a primary queen, guest queen, and 2 guest twin sized beds. Wonderful amenities await for you to relax poolside, get in a workout, or a leisurely game of tennis, Pickleball, or basketball. Rental Terms: Annual: $8,750 Per Month

Exceptional seasonal rental opportunity in the highly sought-after Equestrian Club Estates, ideally located just a golf cart ride from Wellington International. This beautifully renovated, fully turnkey residence offers a clean, modern interior with 4 bedrooms, 4 full bathrooms, plus a separate family/TV room, providing plenty of space for comfortable seasonal living. Enjoy beautiful lake and horse show views from this prime location within one of Wellington's most desirable equestrian communities. The home has been thoughtfully updated throughout and is offered completely furnished and move-in ready for the season. Equestrian Club Estates is exceptionally convenient for riders, trainers, owners and families participating in the Wellington winter season. Rental Terms: Annual: $50,000 Per Month

Welcome to your dream home in the highly sought after gated community, The Isles! This newly renovated haven boasts 4 bedrooms, 2.5 bathrooms, exuding style and sophistication. The open concept design fills every corner with natural light, fostering a seamless flow for entertaining. Admire captivating water views from every angle, perfectly complementing the modern interior adorned with sleek finishes and contemporary touches. Step outside to your own private oasis, featuring a heated pool for year-round enjoyment and a newly installed fire pit. The Isles offers exclusive amenities and convenient access to shopping, entertainment, and all equestrian venues, just minutes away! Don't miss this rare opportunity to rent a slice of paradise!! Rental Terms: Annual: $16,000 Per Month

Enjoy the ultimate Wellington lifestyle in this elegant one-story estate, ideally located in the prestigious, gated community of Palm Beach Polo Club—just minutes from all major equestrian venues, including WEF, Global Dressage, and NPC. This spacious 4-bedroom, 4-bathroom home offers a bright, open layout with soaring ceilings, a split floor plan, two dining areas, a wet bar, and a cozy living room perfect for unwinding after a long day. Three of the bedrooms feature ensuite bathrooms, providing privacy and comfort for guests and family. Outdoors, take in sweeping views of open green space and a tranquil pond from the expansive patio. The heated pool and built-in BBQ make this the ideal spot for entertaining or relaxing in style. Rental Terms: Annual: $25,000 Per Month

Charming 2-bedroom, 2-bath townhouse with loft in desirable Bedford Mews. Bright and tastefully decorated, this inviting home offers comfortable living with spacious interiors and abundant natural light. The versatile loft provides additional space perfect for a home office, den, or guest area. Conveniently located just minutes from the horse show, shopping, dining, and all Wellington has to offer. Available seasonally or short-term during the off-season. A perfect retreat for equestrian season or a relaxing South Florida getaway. *furnishings are similar but slightly different than pictured* Rental Terms: Annual: $6,000 Per Month

An exceptional rental opportunity in the highly sought-after Isles community! This beautifully upgraded 5-bedroom, 3-bathroom residence blends luxury, comfort, and modern convenience in one stunning package. Step outside to your own private oasis featuring a screened-in pool, lush tropical landscaping, fruit trees, and a cozy fire pit—perfect for relaxing evenings or entertaining guests year-round. Ideally located just minutes from the World Equestrian Center and top-rated A-rated schools, this home offers an unbeatable combination of elegance and location. Premium upgrades include a brand-new 2025 roof, whole-house generator, EV charger, smart lighting system, and stylish interior enhancements throughout. Wi-Fi, cable, and ADT security are all included for added convenience and peace of mind. The 5th bedroom doubles as a flex room that could be an office, playroom, or whatever you need. The community has a manned gate for security and offers an array of amenities, including a large pool; gym; sidewalks for walking, jogging, or biking; and pickleball and tennis courts. A rare rental opportunity that truly has it all! Rental Terms: Annual: $7,800 Per Month

Charming 3-bedroom, 2.5-bath home on a beautifully landscaped lot in a quiet, non-HOA community—just minutes from WEF and the Global Dressage Festival. This inviting property features a heated pool and spa, perfect for relaxing or entertaining. Inside, enjoy a bright, open layout with a spacious kitchen and comfortable primary suite. Ideal as a seasonal rental or private retreat, this home offers the perfect blend of comfort and location in one of the area's most desirable equestrian neighborhoods. Rental Terms: Annual: $12,000 Per Month

Step inside this completely renovated and reconfigured masterpiece located behind the prestigious gates of the Palm Beach Polo and Country Club. Every inch of this home was reimagined in 2020 with expanded square footage and high-end finishes, offering an open-concept layout defined by vaulted ceilings and an abundance of natural light. The stunning custom kitchen is equipped with premier Miele appliances, perfectly tailored for both daily culinary experiences and hosting guests. Designed for modern luxury and lifestyle flexibility, the residence features a dedicated executive office enclosed by custom iron and glass doors, alongside a newly added private home gym. Outside, a beautifully curated herringbone brick driveway and striking designer landscaping frame a true backyard sanctuary, complete with a heated saltwater lap pool and an expansive sun shelf. Boasting coveted southwestern exposure over serene water and preserve views, this home delivers magnificent afternoon sunlight and breathtaking sunsets every evening. Complete with all-impact windows and a two-car garage, this turnkey property leaves no stone unturned for the ultimate Wellington lifestyle. Rental Terms: Annual: $21,000 Per Month

Ideally located in the highly desirable Saddle Trail Park neighborhood, this exceptional equestrian property is just a 1/4 mile walk or golf cart ride to Wellington International show grounds. The farm features a premier 14-stall barn with rubber brick flooring throughout, a 210' x 110' arena with premium GGT footing, a 4-horse walker, five grassy paddocks, and a separate lunging area. A set of jumps and tractor with drag are also included. The property also offers staff accommodations with a separate 2-bedroom, 1-bath apartment plus an additional studio apartment. Completing the farm is a beautifully maintained 5-bedroom pool home featuring a desirable three-way split floor plan, spacious primary suite, heated pool and spa, and cabana bath. Rental Terms: Annual: $350,000 Per Month

AVAILABLE FOR THE SEASON! Enjoy the Wellington winter season from this gated and private Paddock Park residence, ideally located near Wellington's renowned equestrian venues. Offering 4,032 sq. ft., this spacious two-story home features 5 bedrooms, 4.1 baths, a private pool, dedicated office space, and ample parking. A separate, fully equipped guest suite offers exceptional privacy and comfort for family, guests, or staff. Surrounded by lush tropical landscaping, the property provides a peaceful and secluded setting while keeping you close to the heart of Wellington. With generous indoor and outdoor spaces, privacy, convenience, and everything needed for an extended stay, this is the perfect place to call home for the Wellington season! Rental Terms: Annual: $15,900 Per Month

Behind the hedgerow you will find this stunning 6-bedroom, 6.5-bath Estate Home in the prestigious Maidstone community of Palm Beach Polo offering unparalleled luxury and privacy. Nestled on a quiet street, this recently renovated home (completed in 2024) boasts new furnishings and has been meticulously designed to provide both comfort and style. Step outside to discover a spectacular pool and garden, perfect for relaxation and entertaining, with endless views of the serene landscape beyond. Exclusive amenities include a state-of-the-art fitness center, tennis and pickleball courts as well as 2 restaurants. Residents have access to the 150-acre Dunes Preserve, which provides scenic walking trails, peaceful sitting areas, and a dog park for all to enjoy. Rental Terms: Annual: $45,000 Per Month

Enjoy the best of Wellington in this spacious 4-bedroom, 2.5-bathroom canal-front home. It has a heated saltwater private pool, and plenty of room to relax and entertain. The open and inviting layout provides generous living space, while the fireplace creates a warm and welcoming atmosphere. The home also features a 2-car garage. Ideally located in Wellington and minutes from the horse show. Rental Terms: Annual: $4,150 Per Month

Exquisitely Renovated 4-Bedroom | 3-Bath Wellington Seasonal Rental | Private Pool | No HOA Enjoy the best of Florida living in this beautifully renovated and meticulously maintained 4-bedroom, 3-bathroom Wellington home. Bright, spacious, stylish, and fully turnkey, it offers modern comfort and effortless living throughout. The private outdoor retreat features a sparkling pool, custom asado grilling area, and fully fenced side yard—perfect for relaxing and entertaining. Ideally located near Wellington's equestrian venues, shopping, dining, parks, and top-rated schools. With no HOA, this home offers privacy and flexibility in a quiet, desirable neighborhood. Available for seasonal rental. Pets considered. Rental Terms: Annual: $9,500 Per Month

An exceptional rental opportunity in the highly sought-after Isles community! This beautifully upgraded 5-bedroom, 3-bathroom residence blends luxury, comfort, and modern convenience in one stunning package. Step outside to your own private oasis featuring a screened-in pool, lush tropical landscaping, fruit trees, and a cozy fire pit—perfect for relaxing evenings or entertaining guests year-round. Ideally located just minutes from the World Equestrian Center and top-rated A-rated schools, this home offers an unbeatable combination of elegance and location. Premium upgrades include a brand-new 2025 roof, whole-house generator, EV charger, smart lighting system, and stylish interior enhancements throughout. Wi-Fi, cable, and ADT security are all included for added convenience and peace of mind. The 5th bedroom doubles as a flex room that could be an office, playroom, or whatever you need. The community has a manned gate for security and offers an array of amenities, including a large pool; gym; sidewalks for walking, jogging, or biking; and pickleball and tennis courts. A rare rental opportunity that truly has it all! Rental Terms: Annual: $7,500 Per Month

Beautifully furnished and completely turnkey 2BR/2BA home in the desirable Bedford Mews community. Features a screened patio, spacious fully fenced backyard, and plenty of privacy. Enjoy access to the community pool and a prime Wellington location just minutes from all equestrian venues. Conveniently close to shopping, dining, grocery stores, schools, and entertainment. A fantastic opportunity for comfortable year-round or seasonal living in the heart of Wellington. Also available seasonal $6500/month (6 month minimum) Rental Terms: Annual: $3,400 Per Month

Beautiful one-story 3 bedrooms,2 bathrooms, Den, home featuring high-impact windows, soaring high ceilings, and stunning water views. The spacious layout offers elegant tile flooring throughout the main living areas, with engineered wood floors in the bedrooms and then for added warmth and style. Enjoy seamless indoor-outdoor living with slidind glass doors that fully retract into pockets, opening the home completely into the porche and backyard. The fenced backyard provides privacy and the perfect setting for relaxing or entertaining by the water. Rental Terms: Annual: $9,500 Per Month