Vacation rentals with a pool in Highland Beach

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Top-rated rentals with a pool in Highland Beach

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, 143 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
A tropical backyard is showcased, featuring a kidney-shaped pool surrounded by palm trees and lounge chairs. A nearby deck area includes a dining table under a vibrant red umbrella. The bungalow's exterior is visible in the background, completing the serene outdoor setting.
Home in Delray Beach
4.91 out of 5 average rating, 211 reviews

Grab Flip Flops & Wine Glasses ✦ RELAX ✦ Welcome!

• 6 blocks to downtown restaurants, boutiques, bars (Atlantic Ave) • 10 blocks to beach 🏝 • 1940's Key West style bungalow & private cottage • Tropical fenced-in backyard, pool & deck • Freebee™ Electric cart rides all over Delray Beach • Cozy, comfy, beachy interior • Secure, keyless entry w/ parking for 3 cars • Coffee + Tea bar • All chef essentials provided, dog-friendly, infant pack-n-play, outdoor BBQ, washer & dryer, beach chairs/towels/umbrella, 2 cruiser bikes, pool floats & more 🏖

Guest favorite
The kitchen features a modern design with white cabinetry, stainless steel appliances, and a spacious island. A wooden beam accents the ceiling. Natural light enters through a window and sliding glass door, which opens to the outdoor space. A dining table with chairs is positioned nearby.
Home in Highland Beach
4.83 out of 5 average rating, 100 reviews

Steps to Private Beach, Pool, Private Patio 19-3

Come stay at this beautifully furnished villa in the exclusive community of Highland Beach. Located directly across from the beach, minutes to Atlantic Avenue in Delray or Mizner Park in Boca Raton. High end finishes throughout in this single story villa showcasing 2 bedrooms, 2 full baths that sleeps 8! Enjoy the 2 car parking, fenced in patio, community pool and private beach access on A1A. Ease of access with only two steps at entry and a keyless entry smart lock. Pet friendly up to 2 pets!

Top guest favorite
A serene outdoor space featuring a heated pool surrounded by palm trees and lounge chairs. A wooden dock extends into the intracoastal waterway, providing a picturesque view. The patio area includes shaded seating arrangements, creating an inviting setting for relaxation.
Condo in Pompano Beach
4.85 out of 5 average rating, 249 reviews

ON CANAL! Pool+Walk to BEACH! Boat Watch! 1b/1b

Beautiful 1 bedroom condo located directly on the intracoastal with a heated pool. This unit DOES NOT have water view from the condo BUT has amazing views of the intracoastal waterway from the patio/pool area. Enjoy watching the yachts sail by along with taking in amazing sunsets from the dock. Work from home, 1 block from the beach! Quiet and peaceful. Within walking distance to many shops and local amenities! Perfect for couples, young families and groups of friends traveling together.

Top guest favorite
The private pool area showcases a sparkling blue pool, complete with a spa and sun loungers beneath vibrant red umbrellas. Lush greenery and tranquil waterfront views create a serene atmosphere, inviting relaxation and enjoyment under a bright blue sky with fluffy white clouds.
Home in Delray Beach
4.94 out of 5 average rating, 126 reviews

Waterfront Htd Pool, Spa, Pool Table, Lanai, Canal

Indulge in this luxurious 4BR 2BA haven on a picturesque waterfront property in a prime location in Delray Beach, FL. This spacious getaway offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, and scenic backyard that will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living + Pool Table ✔ Fully Equipped Kitchen ✔ Screened-In Porch ✔ Backyard (Swimming Pool, BBQ, Dining, Dock) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

Top guest favorite
A charming bungalow is surrounded by lush greenery, featuring a brick pathway leading to the entrance. Potted plants with colorful flowers are placed beside the door. The metal roof reflects sunlight, while the blue sky and clouds provide a serene backdrop.
Home in Delray Beach
4.93 out of 5 average rating, 217 reviews

Charming Beach House with Pool! Great location!

Stroll or bike to beautiful beach and Atlantic Avenue! Please contact me for bookings and availability for short term rentals with a 3 night minimum. 2 beautifully furnished bedrooms with queen beds, 1.5 baths plus outdoor shower. Cable TV and wifi, new linens, pots and pans and appliances. Large outdoor entertainment space with pool, waterfall, gas grill, tropical landscape! A true gem! I also add a pet fee of $150 per pet. We offer instant booking up to one year in advance of your stay.

Guest favorite
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
4.94 out of 5 average rating, 108 reviews

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

☆ 5% Military and First Responder Discount ☆ Escape to our Bali inspired oasis in the heart of Delray Beach! Immerse yourself in the city's vibrant culture while enjoying the local dining and shopping scene. Take a quick ride to the pristine beach for a fun-filled day of swimming, paddle-boarding, and boating, or head over to Lake Ida for a peaceful fishing trip. Unwind in the tranquil amenity filled backyard. Rejuvenate and make long lasting memories with your loved ones. Welcome!

Top guest favorite
A bright living room features light-colored furniture and a mounted television. Large windows with sheer blinds allow natural light to fill the space. A decorative plant adds greenery, and a white coffee table is centered on the wood-look flooring, enhancing the room's airy feel.
Condo in Deerfield Beach
4.92 out of 5 average rating, 107 reviews

1/1 Apartment in Deerfield Beach

Live the ideal beach life! Beautiful, newly remodeled 1 Bedroom / 1 Bathroom unit in Deerfield Beach steps away from the ocean. This fully furnished condo includes pool access, all essential beach equipment, and every other necessity for the perfect beach vacation. The unit is a quick two minute walk to the sand and fishing pier, and is surrounded by great restaurants, shops & nightlife! In addition, the building has been recently upgraded with new balcony railings and fresh paint.

Guest favorite
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
4.92 out of 5 average rating, 141 reviews

Downtown Beach Home w/FREE Beach Cabana membership

Whether you're looking for a winter escape or a much-deserved getaway, our professionally designed, well-appointed, & newly renovated home was created with your family and friends in mind! Enjoy the warm tropical air and Caribbean blue waters of Delray Beach and all of the entertainment and nightlife that Atlantic Ave has to offer. This experience is all about fun in the sun, first-class food and drink, and plenty of laughs with your loved ones. We look forward to hosting you!

Guest favorite
A heated pool invites relaxation, surrounded by a serene yard with tropical palm trees. Colorful floats rest on the water's surface, while sun loungers and conversation chairs provide ample seating for enjoying the outdoors.
Home in Delray Beach
4.95 out of 5 average rating, 126 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

Feel right at home at The Royal House, nestled in a peaceful, private neighborhood perfect for a relaxing family retreat. Experience year-round enjoyment with our heated pool, ensuring an endless swimsuit season. Whether it's day or night, warm or cool, the pool is ready for you to dive in and unwind in a private and peaceful setting. Ideal location: 10 minute drive - Downtown Atlantic Ave 10 minute drive - Beach 5 minute drive - Kings Point 5 minute drive - I-95 & Turnpike

Guest favorite
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.
Condo in Delray Beach
4.87 out of 5 average rating, 220 reviews

Retro charm studio - Walk to beach & Atlantic Ave

Charming studio with vintage vibes in a serene location near Atlantic Avenue—just a 2-minute walk to the beach and Opal Grand Beach Hotel. Step into a bygone era, radiating 1950s nostalgia in one of Delray Beach’s most coveted spots. Enjoy the Grove Condominiums' old-world charm, pool, and tropical gardens. Soak in Delray Beach's retro essence with upscale bars, diners, and boutique shops nearby. Embrace classic charm and coastal living in this slice of the '50s.

Top guest favorite
A clear blue pool occupies the outdoor area, surrounded by a wooden fence and shaded seating under umbrellas. The interior includes a dining table set for four, a modern living room with a television and ample seating, and a spacious kitchen with stainless steel appliances and white cabinetry.
Home in Deerfield Beach
4.94 out of 5 average rating, 102 reviews

Real Big 1BR/BA Unit; Pool; Near Beach

Forget your worries in this spacious and serene, modernized space. An oversized private unit. Self check-in. Full kitchen. Full bathroom. Speedy wifi. 2 Roku tvs. Washer and dryer inside. Need to cool down? Take a swim in the large pool or travel 5 mins (1.5 miles) up to the beautiful Deerfield Beach ocean. Eateries and shops galore in the immediate area, walking distance. Parking limit: 2 vehicles. Book now & enjoy. You won’t regret this stay.

Popular amenities for Highland Beach rentals with a pool

Quick stats about vacation rentals with a pool in Highland Beach

  • Total vacation rentals

    Explore 30 vacation rentals in Highland Beach

  • Nightly prices starting at

    Highland Beach vacation rentals start at G$20,906 GYD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Highland Beach vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland Beach rentals

  • 4.8 Average rating

    Highland Beach stays are highly rated by guests—averaging 4.8 out of 5!