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luxury houses with pool for rent Wellington, United States

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26

House with pool and garden Wellington (United States)

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: $10,000 Per Month

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$10,000 IC / month
3bedrooms
3bathrooms

By Equestrian Sotheby's International Realty

27

House with pool and garden Wellington (United States)

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

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$6,000 IC / month
2bedrooms
2bathrooms
land 650

By Equestrian Sotheby's International Realty

50

House with pool Wellington (United States)

Welcome to this elegant two-story residence enveloped in grand vegetation in Paddock Park of Wellington, offering 4,032 square feet of refined living space. This 5 bedroom, 4.1 bath home provides ample accommodation and convenience for discerning buyers seeking a well-appointed residence. One of the bedrooms is a separate fully equipped guest room. The thoughtful layout spans two floors, maximizing functionality and comfort throughout the property. Located in Wellington near the Winter Equestrian Festival, this single-family home presents an excellent opportunity for those looking to enjoy the Florida winter season. Discover the potential this residence holds for your winter chapter. Rental Terms: Annual: $15,900 Per Month

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$15,900 IC / month
5bedrooms
5bathrooms
land 4,292

By Equestrian Sotheby's International Realty

29

House with pool Wellington (United States)

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

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$7,800 IC / month
5bedrooms
3bathrooms
land 1,418

By Equestrian Sotheby's International Realty

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50

House with pool Wellington (United States)

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: $9,000 Per Month

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$9,000 IC / month
3bedrooms
2bathrooms
land 540

By Equestrian Sotheby's International Realty

40

House with pool Wellington (United States)

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

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$16,000 IC / month
4bedrooms
3bathrooms

By Equestrian Sotheby's International Realty

20

House with pool and garden Wellington (United States)

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

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$6,000 IC / month
2bedrooms
2bathrooms
land 384

By Equestrian Sotheby's International Realty

30

House with pool Wellington (United States)

Beautiful 4 bedroom 2. 5 bath in sought after olympia neighborhood. Tile throughout first floor. Beautiful kitchen with granite countertops and stainless steel appliances, kitchen table that seats 6 comfortably. With desk, pantry and many extras. Open floor plan with formal living room and formal dining room. Large master bedroom with beautifully remodeled master bath. All bedrooms nice size. Community is close to all a rated schools. Equestrian trails elementary, emerald cove middle school, palm beach central high school. Community has pool, clubhouse, exercise room, tennis court, basketball courts inside and out, volleyball courts, playground, water play area

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$5,200 IC / month
239
4bedrooms
3bathrooms

By Barnes Miami

13

House with pool Wellington (United States)

**Updated Townhome with Dual Primary Suites** Available seasonally or annually. Renovated townhome featuring two primary suites plus laundry upstairs, with common areas, a powder room, and a screened patio on the first floor. Includes attached 1-car garage plus 1 space in driveway and community pool access. Conveniently located just 2 miles from Wellington International. Pets permitted with HOA & LL approval. Walking and biking distance to brand new Publix, banks, restaurants and shops. Don't miss this one! $4,500/month furnished seasonal; $3,100/month furnished off-seasonal or annual. Rental Terms: Annual: $4,500 Per Month

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$4,500 IC / month
2bedrooms
3bathrooms
land 159

By Equestrian Sotheby's International Realty

16

House with pool and garden Wellington (United States)

Beautiful, bright and tastefully renovated 4 bedroom house available for the 2024-2025 Equestrian Season. The perfect place to enjoy the winter season in Wellington. Every detail has been carefully planed to provide guests the best stay away from home. Enjoy the Winter Florida weather from your private back yard and experience the totally renovated club house, including state of the art gym, pool and tennis courts. Rental Terms: Annual: $10,000 Per Month

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$10,000 IC / month
4bedrooms
3bathrooms
land 626

By Equestrian Sotheby's International Realty

50

House with pool Wellington (United States)

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

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$350,000 IC / month
8bedrooms
8bathrooms
land 1.1ha

By Equestrian Sotheby's International Realty

49

House with pool Wellington (United States)

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

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$9,500 IC / month
3bedrooms
2bathrooms
land 817

By Equestrian Sotheby's International Realty

48

House with pool and garden Wellington (United States)

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

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$10,000 IC / month
3bedrooms
3bathrooms
land 936

By Equestrian Sotheby's International Realty

29

House with pool Wellington (United States)

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

… 
$7,800 IC / month
5bedrooms
3bathrooms
land 1,416

By Equestrian Sotheby's International Realty

40

House with pool Wellington (United States)

Very private 5 acre property 1 1/2 miles south of main equestrian venues. 6 bedroom, 3 bath furnished house with private pool wrapped by privacy fence, Equestrian amenities include 220' x 180' ring. Two barns 8 stalls each, and ample room for temporary stalls. 4 wash stalls attached to first barn, tack room, feed shed, 10 large paddocks. Maintenance machinery on site. Rental Terms: Annual: $30,000 Per Month

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$30,000 IC / month
6bedrooms
3bathrooms
land 1.8ha

By Equestrian Sotheby's International Realty

35 listings near Wellington

Nearby
43

House with pool and garden Loxahatchee Groves (United States)

Set beneath a canopy of mature oak trees and just 13 minutes from Wellington International, this exceptional equestrian facility features two CBS barns totaling 17 stalls ( 12 stalls & 5 stalls), appointed with custom stall fronts, elegant chandeliers, and quality finishes throughout. A newly constructed 2022 covered arena (98 x 215) with premium GGT footing, Ebb & Flow watering system, custom mirrors, overhead fans, and expansive viewing area delivers a true upper-level experience. Additional equestrian amenities include eight irrigated paddocks with water, a round pen, tack room with lounge, feed rooms, laundry, full bath with wood tile accents, and exceptional groom's quarters. Entire property , including a 5bed/ 3bath pool home, is also available as annual rental (MLS#- B26003504). 15 stalls available for Seasonal dry stalls: $1,500/month per stall Off-season dry stalls: $1,000/month per stall Groom's quarters: $2,500/month seasonal , $1,500/month off-season Rental Terms: Annual: $1,500 Per Month

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$1,500 IC / month
6bedrooms
5bathrooms
land 2ha

By Equestrian Sotheby's International Realty

Nearby
32

House with pool Royal Palm Beach (United States)

Updated 3-bedroom, 2-bathroom home available for seasonal rental. The property features a private pool, outdoor kitchen, outdoor shower, and peaceful water views, offering plenty of space to relax after a day at the horse show. Conveniently located just a 14-minute drive from the Winter Equestrian Festival grounds and a few minutes to Southern Boulevard, this home is ideal for equestrians and seasonal visitors. The updated interior, comfortable layout, and outdoor living space make it a great option for the season. Rental Terms: Annual: $10,000 Per Month

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$10,000 IC / month
3bedrooms
2bathrooms
land 1,290

By Equestrian Sotheby's International Realty

Nearby
50

House with pool and garden The Acreage (United States)

This stunning Ana Maria model is beautifully positioned on an exceptional lakefront homesite within Cresswind Palm Beach, Westlake's highly desirable active adult community. Located on the widest part of the lake, the home enjoys spectacular, expansive water views that create a breathtaking backdrop from both the interior and outdoor living areas. The wide-water setting is truly one of the standout features of this property. The thoughtfully designed residence offers 2 bedrooms, a spacious den that can easily serve as a 3rd bedroom, 2 full bathroomss, and a generous 2-car garage. The home has been extensively upgraded throughout, combining sophisticated finishes with comfortable Florida living. The beautifully appointed kitchen features a 5-burner gas cooktop, stainless steel hood, wall oven and microwave, upgraded soft-close white cabinetry, designer backsplash, quartz countertops, and an impressive, oversized center island offering plenty of space for entertaining and everyday living. Tile flooring extends throughout the main living areas and den. Both bathrooms feature upgraded tile, cabinetry, and quartz countertops, while the spacious laundry room has been enhanced with abundant cabinetry and a utility sink for additional storage and convenience. Outside, the covered patio features a Phantom screen enclosure and provides the perfect setting to relax and enjoy the gorgeous panoramic lake views and peaceful wide-water setting. The spacious backyard also offers plenty of room to add a custom pool, creating the opportunity for an incredible private outdoor retreat. With its premier position on the widest part of the lake, breathtaking water views, extensive upgrades, and beautifully designed living spaces, this exceptional home captures the very best of the Cresswind Palm Beach lifestyle.

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$4,000 IC / month
2bedrooms
2bathrooms
land 607

By One Sotheby's International Realty

Nearby
17

House with pool Greenacres (United States)

Beautifully renovated 3-bedroom townhome located in the desirable Sherwood Lakes community of Greenacres. This bright and updated home features modern finishes, spacious living areas, and comfortable bedrooms that is perfect for easy Florida living. Available as an annual rental. Small pets under 40 lbs welcome. Enjoy community amenities and a convenient location close to shopping, dining, and less than 10 minutes to the turnpike and i95. Rental Terms: Annual: $2,800 Per Month

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$2,800 IC / month
3bedrooms
3bathrooms

By Equestrian Sotheby's International Realty

Nearby
25

House with pool and garden Greenacres (United States)

Beautifully renovated 3-bedroom townhome located in the desirable Sherwood Lakes community of Greenacres. This bright and updated home features modern finishes, spacious living areas, and comfortable bedrooms that is perfect for easy Florida living. Available as an annual rental. Small pets under 40 lbs welcome. Enjoy community amenities and a convenient location close to shopping, dining, and less than 10 minutes to the turnpike and i95. Rental Terms: Annual: $2,800 Per Month

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$2,800 IC / month
3bedrooms
3bathrooms

By Equestrian Sotheby's International Realty

Nearby
50

House with pool Boynton Beach (United States)

Welcome to your dream home in the prestigious gated community of Palm Meadows Estates! This stunning 4 bedroom, 3 full bath, 1-half-bath residence boasts an open floor plan designed for modern living and effortless entertaining. Spanning 2676 sq ft, this home features high-end finishes, abundant natural light, and seamless indoor-outdoor flow. The gourmet kitchen is equipped with premium natural gas appliances, perfect for culinary enthusiasts. Each spacious bedroom offers privacy, comfort and a custom built master closet . Experience true resort-style living with your own private, heated saltwater pool and integrated Jacuzzi. This luxurious outdoor oasis features crystal-clear saltwater filtration, soothing spa jets, putting green and a spacious deck ideal for relaxing or entertaining

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$6,600 IC / month
4bedrooms
4bathrooms
land 607

By One Sotheby's International Realty

Nearby
25

House with pool West Palm Beach (United States)

SoSo cute and cozy 3 bedroom / 2 bath home with a pool available for annual lease. This inviting home features a newly plastered swimming pool, tile floors, all new appliances and ac unit, split bedroom plan and a private backyard with lovely landscaping. Location is very conveniently close to restaurants, schools, shops and beaches! Come see for yourself! Furniture removal negotiable. Rental Terms: Annual: $7,900 Per Month

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$7,900 IC / month
3bedrooms
1bathroom

By Sotheby's International Realty - Palm Beach Brokerage

Nearby
47

House with pool West Palm Beach (United States)

Set on a corner lot along South Flagler Drive, this West Palm Beach residence offers 70 feet of Intracoastal frontage on a 12,197+/- square foot lot with a pool. A thoughtfully integrated addition and a newly constructed guest house with a two-car garage and apartment above further enhance the property's scale, flexibility, and waterfront lifestyle. The residence encompasses approximately 5,712+/- total square feet with five bedrooms, four full bathrooms, and two half bathrooms. From the moment of entry, the home is defined by natural light and sweeping water views. The living room captures the Intracoastal setting, with windows framing the water, and serves as a central gathering space for everyday living. Just beyond, a sunroom with a built-in bar overlooks the pool and loggia and is outfitted with two under-counter refrigerators and an ice maker, well suited for relaxed gatherings and evening occasions. The dining room, featuring herringbone wood floors and a bay window, is surrounded by water views and opens directly to the kitchen, allowing for a natural flow between spaces. The eat-in kitchen is both refined and highly functional, appointed with custom Poggenpohl cabinetry, an internationally recognized German brand known for its precision engineering, clean lines, and exceptional craftsmanship. Dacor appliances include an induction cooktop, large refrigerator and freezer, and two dishwashers, complemented by extensive integrated storage and a dedicated coffee bar. A substantial island, with additional storage, anchors the space and opens to the family room, creating a comfortable layout for daily living. The family room overlooks the pool and terrace, with sliding glass doors enhancing the connection to the outdoors. Also on this level are a full laundry room and a well-appointed guest suite, which features a walk-in closet and an en suite bath with dual sinks, a separate tub and shower, and a private water closet. The upper level is dedicated to the primary suite and additional guest accommodations. The primary bedroom enjoys commanding water views and includes a spacious walk-in closet and a serene bathroom with a separate tub and shower. Two additional guest bedrooms are also located upstairs, each with its own closet and sharing a thoughtfully designed bathroom with dual sinks and a walk-in shower. The guest house, located above the air-conditioned two-car garage, offers exceptional flexibility for extended stays. The apartment includes a living room with a full kitchen featuring an induction cooktop, oven, refrigerator and freezer, and a Bosch dishwasher. The guest bedroom includes closets, an en suite bath, and a washer and dryer. Outdoor living is a defining element of the property. The pool area is anchored by a covered loggia and coquina terrace, connected by a long covered breezeway. A generous gathering area on the western side of the pool includes a built-in grill, cabana bath, and outdoor shower, creating a private setting suited for both relaxation and hosting. Ideally positioned along one of West Palm Beach's most desirable waterfront corridors. Rental Terms: Annual: $40,000 Per Month

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$40,000 IC / month
5bedrooms
6bathrooms

By Sotheby's International Realty - Palm Beach Brokerage

Nearby
27

House with pool Palm Beach (United States)

Palm Beach Perfection! Exquisitely appointed with luxury furnishings. Three bedrooms with updated ensuite baths. Soaring ceilings. Newly refreshed kitchen with new induction cooktop, ovens and refrigerator. New tile roof and entire exterior painted Private courtyard entrance and pool. Just minutes from Worth Avenue, Mar a Lago and The Bath and Tennis club. Ibis Island is just South of the Estate section. Beach access, Par 3 golf course and Phipps Ocean Park and tennis just across the street. Rental Terms: Annual: $30,000 Per Month Off-Season: $20,000 Per Month Winter Season: $40,000 Per Month

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$30,000 IC / month
3bedrooms
3bathrooms

By Sotheby's International Realty - Palm Beach Brokerage

Nearby
19

House with pool Palm Beach (United States)

Location, location, location! This two bedroom, two bathroom apartment in The Rivieria -a small, boutique, doorman building -is on the corner of South Lake Drive and Worth Avenue. Bright-sunny eastern exposure- quiet-full impact windows and doors- full of natural light and clean this apartment is available for a 2026-2027 seasonal lease. The kitchen is renovated and fully equipped and there a queen bed in the main bedroom and two twin beds in the second bedroom-also a pull-out couch in the living room. Close proximity to the Beach, Four Arts, Bike Path, Town Docks and many restaurants, shops and art galleries-this is an ideal, in town, Palm Beach very desirable location. The building has a fitness room, bike storage and a large, beautiful pool area. Rental Terms: Winter Season: $14,500 Per Month

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$14,500 IC / month
2bedrooms
2bathrooms

By Sotheby's International Realty - Palm Beach Brokerage

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