Holiday rentals with a pool in Highland Beach

Find and book unique homes with a pool on Airbnb

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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Guest favourite

Guest house in Boca Raton

4.99 out of 5 average rating, 214 reviews

"Stay Awhile in Boca Raton"

"Stay Awhile" offers travelers a boutique like experience. Our East Boca suite has a private entrance and is located a few minutes drive by car from epic beaches, restaurants and shopping. Our casual suite offers a comfy queen sized bed, a lounge area and a bistro style table for two, that doubles as a work desk. The roomy bathroom has double sinks and a very large shower that is epic. When booking, please be prepared to provide your first and last names of the guest/s and an address too.

7–14 Feb

€ 140 per night

Guest favourite

Apartment in Deerfield Beach

4.85 out of 5 average rating, 143 reviews

The Island Nest, Behind Wyndham Resort on Beach!

The Buccaneer-Ocean Drive(A1A) on the Island .This sparkling clean beautifully furnished unit comfortably sleeps4(King or2 Twin beds &Queen sleeper)Full kitchen,heated pool,onsite laundry, free parking w/no need for car as beach,groceries,shops,nightlife &dining(15+)all within 1 Ocean side block along DBI’s award winning"Blue Wave"Beach. Rated one of FLA’s cleanest beaches! Steps to the viewable ocean scenery,fishing pier and mile of brick paved beachside walking under blowing picturesque palms.

3–10 May

€ 128 per night

Guest favourite

Guest suite in Boca Raton

4.9 out of 5 average rating, 20 reviews

"Beautiful Boca Studio with Enclosed Patio”

Discover Boca Raton's charm from our serene studio, steps away from a public golf course. Offering a queen bed, private patio and a kitchen with modern amenities including a dishwasher. Perfect for beach trips, we provide chairs, umbrella, and towels. Ideal for families, with a car seat, toys and crib on request. Just 7 miles to the beach, immerse in local dining and beachside allure. High-speed Wi-Fi and a dedicated workspace ensure a blend of relaxation and productivity & large community pool.

17–24 Jan

€ 110 per night

Guest favourite

Home in Delray Beach

5.0 out of 5 average rating, 28 reviews

Big saltwater pool house close to beach & the Ave

Relax at this charming getaway near Boca Raton! Enjoy the convenience of early check-in and late check-out (subject to availability). This cozy home boasts a serene atmosphere and is just minutes from the beach, Atlantic Ave, and downtown. Inside, find an open kitchen, dining area, living space, 2 bedrooms, and 2 bathrooms, perfect for 4-6 guests. Unwind in the spacious backyard with a heated saltwater pool, ideal for family fun, BBQs, or romantic evenings under the stars. Book your escape today

26 Jul – 2 Aug

€ 398 per night

Guest favourite

Apartment in Delray Beach

4.82 out of 5 average rating, 129 reviews

Charming 1BR retreat near beach & Atlantic Avenue

Discover Delray Beach’s best-kept secret: our vintage-style 1 bed, 1 bath hideaway. Situated just off Atlantic Avenue behind the luxurious Opal Grand hotel, this cute vintage style 1 bed 1 bath is the perfect place for a beach retreat. Less than a 2 minute walk from the sandy dunes of Delray Beach but both close to the vast array of bars and restaurants and also quietly tucked away. Recently updated this modern & cosy accommodation provides all the comforts of home in a vacation style setting.

4–11 Jul

€ 184 per night

Guest favourite

Home in Boca Raton

4.87 out of 5 average rating, 187 reviews

Updated Classy Fun Big Private, Pool, Game Room

Fresh updated April 2024, Dream Escape in the heart of Boca Raton. Our home welcomes couples and families with an immaculate, tastefully decorated style on a beautiful property with an upscale feel. Perfect for family vacations. Newly remodeled. 4 bedrooms with new, comfortable beds and linens, 2 full bathrooms. Easily sleeps 10. Private heated pool, outdoor bar with BBQ in a very private fenced in backyard. Gem of a house located in a quiet, safe & charming neighborhood. CLEAN. Great locatiin!

22–29 Sep

€ 457 per night

Guest favourite

Villa in Highland Beach

5.0 out of 5 average rating, 29 reviews

Beach, Pool & Private Patio in Exclusive Location

Welcome to this newly designed, family-friendly villa, just steps from the ocean in prestigious Highland Beach! Stay here & enjoy your exclusive gated beach access, outdoor pool, quaint backyard oasis & personal amenities including a beach cart, sun shade, crib, high-chair, makeup vanity & more! Vacation in this safe & secluded slice of paradise, nestled among million-dollar mansions & within minutes of the best shops, dining & nightlife of Atlantic Ave, Delray Beach, Mizner Park & Boca Raton!

6–13 Dec

€ 494 per night

Guest favourite

Home in Delray Beach

4.91 out of 5 average rating, 175 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.

13–20 Apr

€ 239 per night

Superhost

Apartment in Boynton Beach

4.8 out of 5 average rating, 122 reviews

Luxury Near the Beach! Beach pass included!

One-bedroom in Casa Costa luxury complex! offers all the amenities! Enjoy two sparkling pools on the 5th floor landing with views to the Atlantic and over the nature reserve, as well as a fitness center, sauna, social area, three sets of elevators, business center, and 24-hour front desk. Suite includes full kitchen, dining area, living area, separate bedroom with walk-in closet, bathroom with shower and soaktub, balcony, and washer-dryer! Walking distance to restaurant/bars and the beach.

15–22 Sep

€ 132 per night

Guest favourite

Bungalow in Highland Beach

4.88 out of 5 average rating, 42 reviews

Luxury villa beach ,private patio

My place a short walk to a private beach , night life, family-friendly activities, public transport. You’ll love my place for the views, the people, and the location. My place is good for couples, solo adventurers, business travelers, and families (with kids). There is a private patio with a barbecue , table and chairs for dining outside .Great pool with lounge chairs Only available for total of 8 villas to use! Perfect getaway !! This home is surrounded by multi million dollar homes.

1–8 Jul

€ 404 per night

Guest favourite

Home in Delray Beach

4.97 out of 5 average rating, 103 reviews

Downtown Delray Pool Home | Beach Cabana service

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!

16–23 Oct

€ 303 per night

Guest favourite

Flat in Boynton Beach

4.92 out of 5 average rating, 133 reviews

Resort style 1BR/1BA condo

Resort style 1BR/1BA condo located in the luxurious and secure Casa Costa building on the Intracoastal waterway. The amenities of the building are incredible: 24 hours concierge, security, valet parking, pool area at the 5th floor (2 pools), Jacuzzi, gym, sauna, steam room, massage, billiards, business center, conference room.

12–19 Sep

€ 172 per night