Holiday 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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Guest favourite

Guest house in Boca Raton

4.99 out of 5 average rating, 216 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.

11–18 Jan

$172 SGD 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.

27 May – 3 Jun

$138 SGD per night

Guest favourite

Home in Delray Beach

5.0 out of 5 average rating, 30 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

13–20 Sep

$579 SGD per night

Guest favourite

Home in Boca Raton

4.82 out of 5 average rating, 128 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.

4–11 Jan

$728 SGD per night

Guest favourite

Guest suite in Lake Worth Beach

4.97 out of 5 average rating, 275 reviews

Quiet Private Studio w/Pool for One Guest

My Quiet/Private & Beautiful Studio w/ pool is perfect for a single nonsmoking petless professional, golfer, nurse/med student on rotations in Palm Beach centrally located to all area hospitals, the county's many diverse golf courses & the Wellington equestrian community. Private Entrance w/ illuminated off street parking spot, large brand new stone embellished bathroom, granite countertop, mini Kitchen w/ fridge, microwave, and coffee are just a few upscale ammenities inherrent in my place.

8–15 Jun

$141 SGD 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!

31 Mar – 7 Apr

$556 SGD per night

Guest favourite

Apartment 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.

27 Oct – 3 Nov

$194 SGD 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.

30 May – 6 Jun

$376 SGD per night

Guest favourite

Apartment 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.

24 Nov – 1 Dec

$188 SGD 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.

30 Sep – 7 Oct

$311 SGD 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!

5–12 Aug

$334 SGD per night

Superhost

Home in Delray Beach

5.0 out of 5 average rating, 5 reviews

Tropical Oasis 2-Story Delray Beach Home with Pool

Fall in love with our 2-story Key West-inspired pet-friendly home and a rare gem in East Delray Beach! Located just 1 mile from the beach. Within walking distance to Starbucks, Whole Foods, and Target. Less than ten minutes to the famous ''Avenue'' Atlantic Avenue with Delray's upscale shops, art galleries, and fine dining. This home features an open floor plan, a stylish kitchen, a cozy living area, comfortable bedrooms, and great outdoor spaces! Close to everything!

10–17 Sep

$228 SGD per night