Vacation rentals with a pool in Highland 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 🏖

4.78 out of 5 average rating, 77 reviews

Home in Highland Beach

Steps to Private Beach, Pool, Private Patio 23-3

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!!

4.99 out of 5 average rating, 88 reviews

Paradise Palms our tropical oasis in Delray/Boca!

Welcome to Paradise Palms, our tropical oasis! This 3 bedroom, 2 bath home is a perfect getaway to relax and unwind. Enjoy the beautiful pool, hot tub, and tiki hut with gas fire table, bar and TV. There is a wood fire pit, hammock, 4 bikes, 4 beach chairs, snorkeling gear, ping pong and plenty of outdoor games. The interior has all of the comforts of home with a fully equipped kitchen, TV in every room. The property is conveniently located near the beach, downtown Delray, and Boca Raton.

4.94 out of 5 average rating, 124 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!

5 out of 5 average rating, 17 reviews

Apartment in Boca Raton

{Ocean Crest} ~Beach ~ Balcony ~ Pool ~ King Suite

Steps from the sand, this luxurious KING SUITE is your dream beachside escape! ☀️ After a sunny day, relax in the hot tub, swim a few laps in the pool, then fire up the BBQ for your fave grilled bites! 🍔 Inside, unwind in a spacious suite with a private balcony, a plush king bed and a spacious pull-out sofa bed — perfect for couples or small families. The fully equipped kitchen has everything you need! 🍳 Just bring your swimsuit — we’ve got the beach towels, chairs & umbrella! 🏖️

4.93 out of 5 average rating, 106 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!

Superhost

4.94 out of 5 average rating, 145 reviews

DWTN Delray Pool Home | FREE 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 out of 5 average rating, 28 reviews

702A Delray Waterfront, Pool, Tiki Hut + Putting G

DELRAY NIGHTLY presents Waterway Palms, a 3BR/3BA waterfront Delray Beach vacation rental with heated pool, Tiki Hut, firepit, putting green, and outdoor games. Sleeps 8 with king beds, smart TVs, high-speed Wi-Fi, and chef’s kitchen. Enjoy a welcome basket, starter supplies, spacious open living areas, and resort-style outdoor fun. Just 10 minutes from Atlantic Avenue, beaches, dining, nightlife, golf, and upscale shopping. Book your luxury Florida getaway today!

Superhost

5 out of 5 average rating, 3 reviews

Private Home in East Delray w/ Pool & Backyward

Enjoy this beautifully renovated 3 bedroom 2 bathroom home with a private pool in a quiet, safe East Delray neighborhood. Just one mile from the beach & minutes from Atlantic Ave, Mizner Park & FAU. Features a modern kitchen, stylish decor & an inviting outdoor space perfect for relaxing or entertaining. Ideal for families, couples or remote workers. Includes Wi-Fi, smart TVs, washer/dryer & experienced Superhost management for a seamless stay.

4.95 out of 5 average rating, 100 reviews

Villa in The Cove

Modern Lux Home • Beach Nearby • Pool, Gym & Games

ESCAPE TO PARADISE, just 2 miles from the beach! Located in a Quiet Neighborhood. Relax in a home decorated with lots of love: Pool Table, Ping Pong table, a Chef's Kitchen with all you might need. Awesome backyard with a salt system pool and hot tub, spacious Tiki area for outdoor enjoyment, BBQ, mini-golf and color-changing pool lights that creates the perfect ambiance. Read the reviews and reserve your slice of paradise!

4.93 out of 5 average rating, 115 reviews

Heated Pool! 1 Mile To Beach & Atlantic Avenue!

COZY COTTAGE STYLE HOME W/COASTAL FINISHES, BEAUTIFULLY FURNISHED IN THE HEART OF DELRAY BEACH. THIS BEAUTIFUL HOME INCLUDES 3 BEDROOMS & 2 BATHROOMS & A LARGE HEATED POOL! 1 MILE TO THE BEACH, ATLANTIC AVENUE, WATER-SPORT ACTIVITIES, FINE AND CASUAL DINING, NIGHT LIFE & UPSCALE SHOPPING & MINUTES TO BOCA RATON. BEAUTIFUL COVERED PATIO TO GRILL AND RELAX ON SOME LOUNGE CHAIRS WHILE OVERLOOKING THE LARGE HEATED POOL!