Holiday rentals with a pool in Delray Beach

4.97 out of 5 average rating, 65 reviews

Stylish Getaway Near Beach + Atlantic Ave | Pool

Take advantage of early check-in and late check-out when available. Escape to your own private tropical retreat in a prime location, close to Boca Raton. This thoughtfully designed home exudes modern elegance and everyday comfort. Bask in the serenity of the sparkling pool, savor quiet moments by the BBQ, enjoy a family game or relax on the patio surrounded by peaceful greenery and open skies. Atlantic Dunes Park - 7 min drive Atlantic Avenue - 10 min drive Boca Raton/Mizner Park - 11 min drive

4.97 out of 5 average rating, 87 reviews

Direct INTRACOASTAL Waterfront 3BR - Pool & Dock

Relax on your private backyard patio with the famous south Florida intracoastal waterway as your back drop. Sip cocktails & watch the million dollar yachts sail by or throw a fishing line off the dock. This is the BEST Florida home for anyone who loves waterfront living. Sunbathe in the heated pool or fire up the the outdoor kitchen grill or fire pit. Enjoying the outdoor salt life at your very own private resort is what this home is all about. No parties, events or get togethers permitted.

Superhost

5 out of 5 average rating, 4 reviews

Downtown Delray Luxury Pool Villa

Luxurious 4 bedroom/4 bath home in the heart of Downtown Delray, 3 blks from Pineapple Grove, short walk to Atlantic Ave for boutiques, fine dining & beautiful beaches. Indoor/outdoor living w/ lap pool, fire pit & outdoor living space w/TV, Sonos & remote-controlled screens. Downstairs: expansive master retreat, guest bedroom, game room, gourmet kitchen, dining area, laundry room, powder room & family room . 2 bd w/ensuite bathrooms upstairs plus loft. 2-car garage w/electric charging station.

4.99 out of 5 average rating, 91 reviews

Cottage in Delray Beach

Luxury Downtown Tropical Oasis- Pool & fenced yard

Welcome to the Happy Mango Hideaway! This charming cottage is nestled in the heart of the Historic Art District and offers a peaceful retreat from the hustle and bustle of downtown. With heated salt-water pool and private fenced in yard, you can relax and unwind in a tropical paradise. The location of the Happy Mango is unbeatable. You'll be steps away from The Ave's best restaurants, shops and attractions. Whether you're here for a romantic getaway or family vacation, book your stay today.

4.97 out of 5 average rating, 118 reviews

Home in Pompano Beach

•Floasis• Your private FL oasis 5 min to beach!

Kick back, relax and recharge in this calm stylish space! Floasis is located 1.3 miles from the beach, with lots of activities, restaurants and shops nearby... but honestly, once you get to the house you won't want to leave! You will have your own good size pool, a hot tub, an amazing covered deck to relax and dine and a big grassy area for the kids or dogs to run, yoga, relaxation or just for soaking in the florida weather! It's the perfect oasis for a couple, a small family, or 2 couples!

Superhost

4.83 out of 5 average rating, 144 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!

4.92 out of 5 average rating, 198 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.

5 out of 5 average rating, 9 reviews

210 Walk to Pineapple Grove | by Brampton Park

Exclusively Managed By Brampton Park Heated Pool and Pet Friendly 4 Bedroom 3 Bathroom Delightful home, less than 1 mile to the Beach Modern, upscale downtown Delray home, fully renovated with all new furnishings as of July 2024. While this home is on a quiet residential street, the location is truly unbeatable - 1/4 mile to Pineapple Grove district that is bustling with restaurants, bars and cafes, and The Ray Hotel. Half a mile to Atlantic Avenue, and less than 1 mile to the beach.

4.97 out of 5 average rating, 89 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!

4.95 out of 5 average rating, 133 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!

4.96 out of 5 average rating, 116 reviews

Heated Pool | King Bd | Cozy Backyard | Quiet Stay

Feel right at home at The Royal House, nestled in a peaceful, private neighborhood perfect for a relaxing family retreat. Experience year-round enjoyment with our heated pool, ensuring an endless swimsuit season. Whether it's day or night, warm or cool, the pool is ready for you to dive in and unwind in a private and peaceful setting. Ideal location: 10 minute drive - Downtown Atlantic Ave 10 minute drive - Beach 5 minute drive - Kings Point 5 minute drive - I-95 & Turnpike