Holiday rentals with a pool in Wellington

4.95 out of 5 average rating, 141 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

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 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, 312 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.

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, 123 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 serene bedroom features a spacious bed with a patterned headboard, complemented by blue accent pillows. A light wood desk and chair are positioned nearby, with a wall-mounted television providing entertainment. Natural light filters through the window treatments, illuminating the soft, neutral color palette.

4.93 out of 5 average rating, 114 reviews

Cozy Beach Queen Chic-Palm Beach Island-near Beach

Cozy Chic Beach Queen, inspired by mid century modern decor includes a shower/bath & task desk. This historic Palm Beach Hotel Condo is just 1 1/2 blocks to the beach or relax by our heated pool. World class restaurants in walking distance. No car is needed but valet parking is $15 a day from 8 a.m. til 11 p.m. Please inform if bringing a car & park in front for 15 min only check-in and ask for parking placard in mailbox 3018. Please return the placard when departing or result in a $50 fee.

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, 483 reviews

Key West Style Suite with Pool/Spa

This beautiful Key West Style studio with kitchen and WIFI is located in the historic neighborhood of Flamingo Park. It’s close to restaurants, downtown Rosemary Square, the Norton Art Museum, the WPB Convention Center, the Palm Beach International Airport, the instracoastal waterway and 5-10 minUte drive to Worth Avenue in Palm Beach and the Palm Beaches. We welcome couples, solo adventurers and business travelers who can enjoy a private backyard guest suite with salt water pool and spa.

4.85 out of 5 average rating, 117 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.

5 out of 5 average rating, 114 reviews

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.

Home in Dreher Park

Jungle Oasis with Heated Pool, Tiki Hut & Hot Tub

Welcome to your sunny West Palm Beach getaway. This beautiful home offers a heated pool, perfect for relaxing after a day of exploring the town or nearby beach. Conveniently located, it's just minutes from the PBI airport and downtown West Palm and a short walk to the zoo making it an ideal day out for families. The house has 3 spacious bedrooms, 2 modern bathrooms, and a fully stocked kitchen, providing all the comforts of home in a tropical setting. Enjoy the Florida sunshine in style!

An aerial view captures a scenic mix of urban architecture and lush greenery. Buildings feature red-tiled roofs and flat rooftops, while the waterfront is lined with trees. The blue water glistens in the distance against a backdrop of clear skies.

4.91 out of 5 average rating, 346 reviews

🌞Palm Beach🌴view studio by the🏖 w/parking⚡wifi

🌴🏖Beautiful remodeled Palm beach island garden/pool view 275 sf. studio available in the historic Palm Beach Hotel 2.5 blocks to the Beach. Includes a parking pass for free parking nearby. Newly furnished with large comfortable King Simmons Beauty Rest Platinum bed kitchen and a great view of a garden and partial view of the pool! Dining, bars & beach within 2 blocks and a Publix across the street, beautiful pool on-site. Parking passes are included with your stay🏖🌴

Guest house in Palm Beach Gardens

A large swimming pool is surrounded by lush tropical vegetation, featuring several loungers and umbrellas in calming shades of blue. The clear water reflects the vibrant greenery, creating a serene outdoor space ideal for relaxation and enjoyment.

4.99 out of 5 average rating, 254 reviews

WHISPERING PALMS

Located in our highly secure gated community, this artfully furnished 3 room Villa has a true Florida vibe. Only a quarter mile from PGA Golf Club; minutes from the beach; tropical gardens, and a large swimming pool make this property truly unique. This is an AWARD WINNING GUEST HOME!! LARGE PRIVATE POOL. NEVER SHARED! FOR GUESTS ONLY! Screened in wooden deck is a perfect place to relax and enjoy your morning coffee or a glass of wine in the evening.

4.99 out of 5 average rating, 119 reviews

Home in Flamingo Park

Luxe Designer Home • Heated Salt Pool • Palm Beach

Enjoy a private Flamingo Park retreat with a heated saltwater pool, lush yard, and bright modern interiors. This renovated historic home offers a sleek Italian kitchen, comfortable lounge & dining areas, fast WiFi, smart TV, and Sonos soundbar. Walk to cafés, restaurants, and the Norton Museum. Minutes to beaches, golf, and a family-friendly park with tennis and new pickleball courts. Great for families or business stays.

4.88 out of 5 average rating, 105 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

Cozy place located in a great area in Royal Palm Beach. Everything you need is less than 5 mins away, including Walmart, Publix, Starbucks, Wellington mall, and various food places. The home itself is packed with amenities that will make you not want to leave. This includes a screened in pool, patio with Grill, a lake for fishing and kayaking, and a game room with pool table and other games. Very family friendly.

4.94 out of 5 average rating, 304 reviews

Flat in Flamingo Park

New Studio Apartment w/ Kitchen - A

This quaint and private apartment is newly remodeled and located in the heart of West Palm Beach. This suite is perfect for the weekend get-away or for those looking to thaw out for a few months and escape from the cold. Conveniently located near: - Beach - Flagler Museum - Breakers Hotel - Downtown West Palm - Norton Museum - Kravis Center - Convention Center - Great Restaurants .. And so much more

Popular amenities for Wellington rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 39 reviews

A private outdoor space is presented, featuring a sparkling salt-water pool accompanied by a hot tub. Colorful umbrellas provide shade over spacious loungers, while a cozy seating area and dining table enhance the inviting atmosphere. Ambient lighting complements the tranquil evening sky.

Home in Lake Worth

NEW POOL + SPA! Historic Downtown Beach House Gem

4.93 out of 5 average rating, 116 reviews

A private backyard features a heated pool surrounded by sun loungers and a thatched tiki hut. Soft lighting enhances the serene atmosphere, while palm trees and a grassy area create a tranquil oasis. A stunning sunset sky adds color to the scene.

Home in Delray Beach

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

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.

4.73 out of 5 average rating, 89 reviews

Cozy Home with Pool & Spa (Heated) in Wellington

4.9 out of 5 average rating, 145 reviews

Beach chairs are set up under large blue umbrellas on white sand. The tranquil ocean waves can be seen in the distance, blending into a clear sky with soft clouds. A sign indicates that a beach membership is included with the stay.

Home in Delray Beach

Downtown Beach Home w/FREE Beach Cabana membership

An open-concept living area showcases a warm blend of neutral tones and wooden accents. Comfortable seating is arranged on a textured area rug, complemented by a dining table in the background. A kitchen with modern appliances and wooden cabinetry can be seen, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 45 reviews

Sunny De-Lite / Equestrian Center / Wellington

Home in Palm Beach Gardens

A welcoming living area is presented with comfortable seating and a modern coffee table. Light-colored walls create a bright atmosphere, and natural light is invited in through a large window. A dining area is visible in the background, featuring a table surrounded by chairs.

4.98 out of 5 average rating, 133 reviews

Quaint & beautiful PGA National Club Cottage

4.96 out of 5 average rating, 101 reviews

Home in Boynton Beach

Canal, Htd Pool, Putt-Putt, Pergola, Air Hockey

4.97 out of 5 average rating, 106 reviews

Home in Singer Island

Htd Saltwater Pool! Walk to BEACH! PingPong! BBQ!

Apartment rentals with a pool

A bright bedroom features a spacious bed adorned with vibrant pink and green bedding. Fluffy pillows add texture, while large windows allow natural light to fill the space. An elegant lamp beside the bed complements the room's decor, and a wardrobe stands against the wall.

4.98 out of 5 average rating, 202 reviews

The Lilly Pad: A Lilly Pulitzer- Inspired Condo

Apartment in Boynton Beach

A comfortable living area is featured, with a light-colored sofa adorned with decorative pillows and beach-themed artwork on the walls. A wooden coffee table with a coastal design sits in front, complemented by a patterned area rug, creating a relaxed atmosphere.

4.93 out of 5 average rating, 174 reviews

Tropical Coastal Resort in Boynton Beach

A vibrant studio features colorful floral wallpaper and a spacious bed with light bedding. A cozy seating area is adorned with a decorative throw. Natural light enters through three windows, and a large flat-screen TV sits on a wooden console, adding to the lively ambiance.

4.92 out of 5 average rating, 133 reviews

Mermaid King bed Suite- heart of PB + Free Parking

Apartment in Singer Island

4.91 out of 5 average rating, 131 reviews

Ritz-Carlton Beach Residence by Guaranteed Rental

Apartment in Palm Beach Gardens

The entryway leads into a bright, open space with warm wood tile flooring. A modern kitchen bar with two white stools is visible, along with dark cabinetry and stainless steel appliances. Natural light enters through nearby windows, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 181 reviews

Clean quiet updated 2 bdrm golf villa PGA National

Apartment in Delray Beach

A sandy path leads to the beach, bordered by lush green vegetation on either side. Wooden posts with ropes define the walkway, which opens up to a view of the blue sky and the distant ocean, creating an inviting coastal atmosphere.

4.87 out of 5 average rating, 228 reviews

Retro charm studio - Walk to beach & Atlantic Ave

Apartment in West Palm Beach

A modern resort building features a clean architectural design, surrounded by palm trees and vibrant landscaping. The Marriott Vacation Club sign is prominently displayed in front, indicating the welcoming nature of the property.

4.88 out of 5 average rating, 161 reviews

Marriott Ocean Pointe Guest Room/Studio

A bright sleeping area features a spacious bed with white bedding, complemented by light wood furniture. Large windows allow natural light to fill the room, framed by soft white curtains. Decorative elements include ceiling beams and a potted plant, enhancing the welcoming ambiance.

4.96 out of 5 average rating, 228 reviews

Ultimate Palm Beach Island with Grand Terrace

Other holiday rentals with a pool

Cottage in Palm Beach Gardens

A modern living area features a spacious beige sofa and two comfortable gray armchairs, placed around a glass coffee table. Large sliding glass doors provide views of the backyard, allowing natural light to brighten the room. A sleek entertainment unit is mounted on the wall, elegantly showcasing candles.

5 out of 5 average rating, 20 reviews

The Edwardian cottage at PGA

4.81 out of 5 average rating, 21 reviews

Cottage in Greenacres

Cozy Cottage LW near Beach

4.84 out of 5 average rating, 83 reviews

The private screened-in pool area features a crystal-clear pool with a lighted waterfall, surrounded by lush landscaping. Soft accent lighting enhances the ambiance, while a serene sunset illuminates the sky beyond. Comfortable lounge chairs provide an inviting spot to relax.

Villa in Wellington

Sunshine Escape! Equestrian Resort! Wellinton-WPB

An enclosed outdoor area features a private swimming pool surrounded by a spacious deck. Lounge chairs are placed for relaxation, and a poolside seating area is visible. A basketball hoop is present, along with a jacuzzi and a screened-in design providing protection from insects.

5 out of 5 average rating, 13 reviews

Elegant, 4 BDR house with a pool

4.88 out of 5 average rating, 50 reviews

An outdoor area features a swimming pool, surrounded by lush greenery and palm trees. A seating area with plush cushions is visible, alongside a shaded lounge space. The outdoor kitchenette is equipped for convenience, enhancing the overall functionality of the space.

Flat in West Palm Beach

Charming little apartment with pool

5 out of 5 average rating, 25 reviews

The outdoor space features a heated pool, surrounded by lush greenery and palm trees. Soft lighting highlights the pool and patio area, where lounge chairs and a dining table are placed under an umbrella, creating a serene setting for relaxation.

Home in Lake Worth Beach

M&M's Oasis

5 out of 5 average rating, 13 reviews

Home in West Palm Beach

Heated Pool Oasis West Palm Beach Pet Kid Friendly

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.