Vacation rentals with a pool in Highland Beach

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Top-rated rentals with a pool in Highland Beach

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Guest favorite

Guesthouse 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.

Aug 8 – 15

G$20,466 GYD per night

Guest favorite

Condo in Deerfield Beach

4.84 out of 5 average rating, 117 reviews

Large 2 BR 2 Bath at The Buccaneer by the beach!

This condo has been recently renovated and is the largest unit in The Buccaneer in Deerfield Beach. The total square footage is over 1,300 square feet and has central Air Conditioning. Included is a washer/dryer and is a very desirable rental for monthly or seasonal. Both bathrooms and kitchen have been remodeled. 2 Parking Spaces included. Short walk to the beach, fishing pier, shops and restaurants of Deerfield Beach! queen size futon in the master bedroom and a sofa bed in the living room.

May 8 – 15

G$30,190 GYD per night

Guest favorite

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.

Dec 27 – Jan 3

G$20,327 GYD per night

Guest favorite

Home in Delray Beach

5.0 out of 5 average rating, 29 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

G$87,731 GYD per night

Guest favorite

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.

Feb 27 – Mar 6

G$100,145 GYD per night

Guest favorite

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!

Nov 19 – 26

G$72,495 GYD per night

Guest favorite

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.

Jul 31 – Aug 7

G$57,116 GYD per night

Guest favorite

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 13 – 20

G$28,489 GYD per night

Guest favorite

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 28 – Oct 5

G$47,001 GYD per night

Guest favorite

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!

Sep 25 – Oct 2

G$54,370 GYD per night

Guest favorite

Home in Delray Beach

5.0 out of 5 average rating, 18 reviews

The Vacation Getaway with a Heated Salt Water Pool

Are you looking to escape the cold, work, or just be close to the beach? If so, this stunning vacation home is for you. It includes a saltwater pool with heater, and is minutes away from the beach, restaurants and all that Atlantic Avenue has to offer. You can rest easy knowing that the owners are dedicated to giving you your best vacation experience.

Jul 26 – Aug 2

G$65,445 GYD per night

Guest favorite

Apartment 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.

Jul 21 – 28

G$28,844 GYD per night