Vacation 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 favorite

Home in Delray Beach

4.89 out of 5 average rating, 186 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 🏖

Guest favorite

Villa in Highland Beach

5 out of 5 average rating, 45 reviews

Beach, Pool & Private Patio in Exclusive Location

Newly designed, family-friendly, luxury villa, just steps from the ocean, offering members-only, gated access to prestigious Highland Beach! Enjoy the convenience of a pool at your doorstep, peaceful tropical patio for relaxing, and private beach for tranquility and fun. A safe and secluded paradise nestled among multi-million-dollar mansions, and within minutes of the best shops, dining, and nightlife of Atlantic Ave, Mizner Park, and Boca Raton. Your perfect beach escape is just a click away!

Guest favorite

Home in Highland Beach

4.83 out of 5 average rating, 83 reviews

Steps to Private Beach, Pool, Private Patio 19-3

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!!

Guest favorite

Condo in Delray Beach

4.86 out of 5 average rating, 195 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.

Superhost

Guesthouse in Parkland

4.81 out of 5 average rating, 175 reviews

Parkland Private Guesthouse

Your private 1,000 sf studio guesthouse is located on 1.2 acre estate in prestigious Parkland. Complimentary bottle of wine, vanity set, coffee K-cups, down pillows and down duvet comforters included with all stays. Your getaway is secluded enough to hear birds & crickets in the day and see all the stars at night yet just a 10 min walk to a large shopping center. This suite is for guests seeking a luxury stay who come for work or pleasure, alone or with family. Your comfort is our pride.

Guest favorite

Home in Boca Raton

4.87 out of 5 average rating, 196 reviews

Family Getaway | Private Pool | Entertainment

Welcome Home Nestled in a safe, family-oriented neighborhood, our spacious home offers a peaceful getaway for all guests. Family-Friendly: Saltwater pool and game room. Comfortable and Relaxing: Spacious, clean, and cozy. Outdoor areas for sunbathing and fireplace evenings. Explore with Ease: Walk-friendly area near stores and restaurants. Bikes available. Amenities Galore: BBQ grill, outdoor fireplace, and more. Seamless Experience: Great communication, smooth check-in, and check-out.

Guest favorite

Home in Delray Beach

4.83 out of 5 average rating, 131 reviews

LUXURY!i - Heated Pool - Perfect Vacation

Beautiful Key West-style house with a gorgeous heated pool. LUXURY! High-end furniture, real wood beds & extremely comfortable mattress. NO IKEA beds here ;) Two story house, 4 bedrooms, 3 full bathroom Heated pool & screened patio Whole Foods, Starbucks, Chick-fil-A, Trader Joe's, Target and so much more just a step away. Located on a quiet, family oriented "no outlet" St 3 min ride to amazing beach, or relax time in the hammock by the pool? Stay with us for YOUR PERFECT VACATION!

Guest favorite

Home in Delray Beach

4.93 out of 5 average rating, 174 reviews

Delray Beach-5 Bedr/4.5 bath*Heated Pool

Huge comfortable 5 bedroom, 3 ensuite & 2 half bathroom house in sought after Lake Ida area, Delray Beach, FL. Step into a relaxing, beach feel the moment you walk through the door. Enclosed backyard with large private heated pool. Beachtowels, towels, toiletries and all kitchen amenities included. Delray Public Beach: 2miles World renowned Delray Tennis stadium: 1.2 miles. Buzzing Atlantic Ave with restaurants, art galleries: 1 mile Pool loungers, umbrellas & grilling facilities outside.

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.

Guest favorite

Home in Delray Beach

4.94 out of 5 average rating, 120 reviews

Downtown Beach Home w/FREE Beach Cabana membership

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!

Guest favorite

Rental unit in Delray Beach

5 out of 5 average rating, 5 reviews

Beautiful Beachside Condo!

Enjoy a stay at this peaceful and centrally-located place. Beautiful Corner Unit, full one bedroom with King bed. Walk to the beach and Atlantic Ave. Outdoor Heated Pool. The Best Location around and it includes free parking. Can rent weekly or monthly. Located next to the Ocean front Marriott and Opal Grand Hotel. Full kitchen with appliances. Stay here for a fraction of the price of the Marriott and enjoy this corner unit full one bedroom 675 square foot apartment.

Superhost

Rental unit in Delray Beach

4.81 out of 5 average rating, 113 reviews

Beach Studio Steps from Ocean & Atlantic Ave

Wonderful opportunity to stay in a modern beach studio literally steps away from the stunning sandy dunes of Delray Beach. This property provides ideal accommodation for anybody wanting to stay central to Atlantic Avenue, close to the array of fantastic bars and restaurants the area has to offer, but also conveniently tucked away to provide that serene get away feeling that being close to the ocean provides.