Vacation rentals with a pool in Wellington

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Top-rated rentals with a pool in Wellington

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

A vibrant outdoor space is surrounded by palm trees and lush plants, featuring a splash pool and a hammock. Soft grass covers the ground, leading to a charming cottage with a welcoming red door visible in the background.

Cottage in Lake Worth Beach

4.99 out of 5 average rating, 138 reviews

Private & Pet Friendly, Key West-King Bed Cottage

Spend your beach getaway at our cozy and colorful cottage. It’s one of the historic cottages of Lake Worth Beach listed in a bestselling book 'The Cottages of Lake Worth'. Sit back, soak up the sun, and enjoy the splash pool in the private yard, a palm tree paradise. Relax completely in the specious king-bed bedroom. In a walking distance from the cottage are the Lake Worth public beach and Downtown with a variety of restaurants and entertainment venues. Community Golf Club is around the corner.

Guest favorite

The outdoor area is highlighted by a swimming pool surrounded by a sun patio. Comfortable lounge chairs and a dining set are positioned nearby. The landscaped yard features decorative stones and lush green grass, with a fence providing privacy. The building's exterior is inviting under a bright sky.

Home in West Palm Beach

4.95 out of 5 average rating, 133 reviews

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.

Guest favorite

Apartment in Flamingo Park

4.92 out of 5 average rating, 175 reviews

Remodeled Downtown Apartment #1

This newly remodeled 2 bedroom, 1 bathroom apartment features an open concept layout with a full kitchen and large living space. Most of the furnishings are sourced from Restoration Hardware and you are sure to feel at home with the greenery and thoughtful decor throughout. The master bedroom has a king size bed and the second bedroom also has a king size bed. Both have large closets with plenty of storage space. The bathroom has a beautiful custom, walk-in shower. Only 2 blocks from the water!

Superhost

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.

Home in Wellington

4.79 out of 5 average rating, 303 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.

Top guest favorite

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.

Home in Wellington

4.99 out of 5 average rating, 122 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!

Top guest favorite

A tranquil saltwater pool features a stylish spa with a gentle waterfall cascading into the main pool. The pool is surrounded by well-manicured grass and modern landscaping, providing a serene outdoor space for relaxation.

Guesthouse in Flamingo Park

4.98 out of 5 average rating, 460 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.

Guest favorite

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

4.84 out of 5 average rating, 116 reviews

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.

Top guest favorite

Home in Wellington

5 out of 5 average rating, 18 reviews

Saddle Up in Style

Escape to this stylish Wellington retreat in the heart of horse country—minutes from stables, shows, and races. Enjoy a chef’s kitchen, and spacious outdoor dining perfect for family meals. Unwind with ping pong, board games, or a cozy movie night. For those working on vacation (seriously, why?), there’s a desk and monitor ready to go. We won’t judge—just don’t forget to hit the pool after those emails. Whether you're here for the equestrian scene or just to relax, this home has it all.

Guest favorite

An inviting outdoor space features a hot tub surrounded by wooden decking, with low-maintenance plants enhancing the area. Soft lighting creates a warm ambiance under a starlit sky, while comfortable seating areas are visible, ideal for relaxation and entertainment.

Home in West Palm Beach

4.98 out of 5 average rating, 164 reviews

Bio Hacker Resort! Pool, Sauna, ColdPlunge, HotTub

West Palm Beach Oasis! Explore a luxurious 3BR/2BA resort-style escape that sleeps up to 8 guests. Relax by the sparkling pool, unwind in the sauna, or enjoy movie nights at the outdoor theater. The game room & Tiki Bar make this the ideal spot for entertainment. Stylish decor, an 85" Smart TV, & modern amenities create the ideal setting for relaxation. At Russi Retreat, you're not just booking a stay; you're securing a private sanctuary in South Florida. Book your stay today!

Guest favorite

Home in West Palm Beach

4.96 out of 5 average rating, 164 reviews

Perfect pool house

Beautiful, clean, and super comfortable home with room to stretch out. In beautiful neighborhood in central West Palm Beach. The home was just remodeled with the best quality furniture, bedding, and linens. The home has all the essentials, and none of the clutter. The pool and patio is gorgeous, and Very private. You will spend most of your time in the backyard. Grilling, dining, swimming, and lounging. The house is perfect for entertaining and relaxing with the family. Enjoy!

Guest favorite

A refreshing pool area is featured, bordered by a white fence and lush greenery. Two lounge chairs are positioned beside the pool, along with a colorful beach ball floating in the water. Palm trees provide a serene backdrop against a clear blue sky.

Home in Royal Palm Beach

4.88 out of 5 average rating, 155 reviews

Big Pool House/ Great Area/ 3bdrms and 2 baths

Beautiful 1 story Home. POOL , SMALL CANAL IN THE BACK 3 bdrms+ 2 full bathrms 8 guests. Pet friendly (Max 2 dogs) Great for families looking for a peaceful getaway. Bbq grill (propane provided). Great location! 15- 20 minutes from downtown WPB and Palm Beach International. Easy 25- 30 minutes access to closest beach. Shops, Restaurants, Target: 5 - 10 minutes away. Parking on premises 3 cars on driveway. POOL NOT HEATED. NO HOT TUB ON PREMISES. $50 PET FEE/PER PET

Top guest favorite

The serene pool area is illuminated by string lights, reflecting off the inviting water. A relaxing atmosphere is created with lounge chairs and colorful pool toys, while the surrounding fenced yard offers privacy for enjoyment.

Home in Palm Beach Gardens

5 out of 5 average rating, 146 reviews

Heated Pool•Near Beach•Pet Friendly

Welcome to South Florida! You’ll feel like you are at your own private resort when you take a dip in the heated pool surrounded by tropical greenery and an ocean breeze. The 1,368 sq. ft. home features an updated open floor plan w/ large kitchen and bar to host friends & family. The prime location puts you minutes away from the best beaches, and just up the road from the best shopping, dining, and nightlife options. Quiet street! No parties!