Vacation 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guesthouse 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.

Feb. 4 – 11

$206 CAD 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.

Aug. 11 – 18

$163 CAD per night

Guest favourite

Home in Boca Raton

4.98 out of 5 average rating, 47 reviews

EAST BOCA RATON 1MILE TO BEACH! PRIVATE POOL HOME!

Artsy CLEAN contemporary private home, totally updated. (5*STAR rated VRBO) Located in a quiet, charming neighborhood 5minutes from the beach! Private*NEW ELECTRIC*HEATED SALT POOL! Great location in the heart of East Boca! Very close to restaurants, grocery store,FAU, beautiful Mizner Park, shops. Comfy mattresses, free high speed WiFi, free parking,2 flat screen TV’s and cable w/ ability to record shows. Master bath has jetted jacuzzi tub. Updated kitchen with lots of cookware. Come and enjoy!

Feb. 3 – 10

$795 CAD 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

Sep. 13 – 20

$679 CAD 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!

Aug. 29 – Sep. 5

$667 CAD per night

Guest favourite

Home in Boca Raton

4.82 out of 5 average rating, 127 reviews

1mi to Beach 2 Suite 4bd/3bth Home with Pool &Spa

Newly renovated house with amazing heated saltwater pool and spa just a mile away from some of the best beaches in the U.S and convenient to shopping, restaurants and transportation. Located in a quiet, family oriented neighborhood , our house comes with two master suites , a full kitchen, comfortable memory foam beds , large theater TV , fast Wifi , Keurig with included coffee , bbq grill plus many other extras. Its the perfect place for a quiet, relaxing and private family beach getaway.

Feb. 4 – 11

$787 CAD 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!

Sep. 29 – Oct. 6

$490 CAD per night

Guest favourite

Condo in Delray Beach

4.85 out of 5 average rating, 168 reviews

Retro charm studio steps from beach & Atlantic Ave

Charming studio with vintage vibes and a serene location near Atlantic Avenue, and a 2-minute walk from the beach & Opal Grand Beach Hotel. Step into a bygone era, exuding the nostalgic vibes of the 1950s in one of Delray Beach’s most coveted locales. Enjoy the Grove Condominiums with its old-world charm, pool, and tropical gardens. Experience Delray Beach's retro essence with upscale bars, diners, and boutique stores nearby. Embrace classic charm and coastal living in this slice of the '50s.

Nov. 6 – 13

$221 CAD per night

Guest favourite

Condo in Boynton Beach

4.96 out of 5 average rating, 52 reviews

The Sand Dollar! Casa Costa facing East, King Bed

KING-BED! Beautiful new vacation rental in gorgeous Casa Costa! Feel your stress melt away when you walk into this light and breezy treasure - The Sand Dollar. This one-bedroom condo is situated on the second floor, facing east over the reservoir and nature reserve, providing heavenly sunrise views. A ten-minute walk takes you over the intracoastal to the sandy beaches of Boynton..... The complex also offers a business center, men's and women's saunas, and a fitness center.

Nov. 16 – 23

$217 CAD 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.

Sep. 25 – Oct. 2

$419 CAD 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!

Jul. 30 – Aug. 6

$410 CAD per night

Guest favourite

Tiny homes in Delray Beach

4.95 out of 5 average rating, 82 reviews

Private Escape; Mini Pool

This super cute tiny home is located in a quiet residential neighborhood. It offers a queen size bed, speedy wifi, full kitchen, bathroom w/ spacious walk-in shower, and 1 smart tv. Simple, cute, clean, minimalist-- yet all of the basic essentials needed for your stay. There's also a private plunge pool on site to cool down and relax. Want to venture out instead?..The beach and downtown area are only 2 miles away! Hurry & book!

May 20 – 27

$220 CAD per night