Vacation rentals with a pool in Delray Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delray Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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 15 – 22

R1,797 ZAR per night

Guest favorite

Home in Boynton Beach

4.89 out of 5 average rating, 160 reviews

CASA DE CONCHA - 3/2 POOL Home in Boynton Beach!

Conveniently located in central Boynton Beach with easy access to both I-95 and the FL Tpk, and only 4 miles to the beach, this charming and tastefully appointed 5 * rated 3/2 pool home offers exceptional comfort (new mattresses, loaded with amenities), leisure (private enclosed pool, outdoor dining area, fire pit), AND utility (fully equipped kitchen, grill, home office) for families and business travelers alike! Come stay with us and enjoy the benefits of an EXPERIENCED SUPERHOST-managed home!

Aug 2 – 9

R2,650 ZAR per night

Guest favorite

Home in Delray Beach

4.95 out of 5 average rating, 59 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.

Jun 22 – 29

R13,508 ZAR per night

Guest favorite

Condo in Delray Beach

4.82 out of 5 average rating, 129 reviews

Charming 1BR retreat near beach & Atlantic Avenue

Discover Delray Beach’s best-kept secret: our vintage-style 1 bed, 1 bath hideaway. Situated just off Atlantic Avenue behind the luxurious Opal Grand hotel, this cute vintage style 1 bed 1 bath is the perfect place for a beach retreat. Less than a 2 minute walk from the sandy dunes of Delray Beach but both close to the vast array of bars and restaurants and also quietly tucked away. Recently updated this modern & cosy accommodation provides all the comforts of home in a vacation style setting.

Sep 11 – 18

R4,059 ZAR per night

Guest favorite

Cottage in Delray Beach

4.91 out of 5 average rating, 23 reviews

Historic beach cottage with private pool!

Welcome to Chateau Mango, a historic Old Florida cottage in the heart of historic Delray Beach, FL. Walk just 4 blocks south to bustling Atlantic Avenue for amazing restaurants and shops. This one of a kind cottage is within 1.5 miles of the beach. The most memorable part of your experience might be lounging by our private lagoon style pool. Have coffee on our cozy front porch complete with porch swings. Our cottage is also features a fully outfitted kitchen. Stay a long weekend or a month.

Sep 6 – 13

R7,005 ZAR per night

Guest favorite

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 327 reviews

Key West Style Suite with Pool/Spa

This beautiful Key West Style studio with kitchen and WIFI is located in the historic neighborhood of Flamingo Park. It’s close to restaurants, downtown Rosemary Square, the Norton Art Museum, the WPB Convention Center, the Palm Beach International Airport, the instracoastal waterway and 5-10 minUte drive to Worth Avenue in Palm Beach and the Palm Beaches. We welcome couples, solo adventurers and business travelers who can enjoy a private backyard guest suite with salt water pool and spa.

Sep 22 – 29

R2,610 ZAR 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.

Nov 5 – 12

R6,592 ZAR per night

Guest favorite

Condo in Boynton Beach

4.84 out of 5 average rating, 117 reviews

One bedroom in Lux condo,Casa Costa! w/beachpass!

One-bedroom in Casa Costa luxury complex! offers all the amenities! Enjoy two sparkling pools on the 5th floor landing with views to the Atlantic and over the nature reserve, as well as a fitness center, sauna, social area, three sets of elevators, business center, and 24-hour front desk. Suite includes full kitchen, dining area, living area, separate bedroom with walk-in closet, bathroom with shower and soaktub, balcony, and washer-dryer! Walking distance to restaurant/bars and the beach.

Oct 17 – 24

R2,464 ZAR 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 12 – 19

R2,574 ZAR 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!

Jul 13 – 20

R5,125 ZAR per night

Guest favorite

Home in Delray Beach

5.0 out of 5 average rating, 61 reviews

The Dream Delray/ 4 BR En-suite Pool Home

Dreams Delray is a modern 4 bedroom 4 1/2 bathroom (4 Bedroom En Suites) heated pool home which is a 10 minute walk to "The Ave,” Delray Beach's popular downtown venue, and a short 5 minute drive to our famous sandy beaches. It has everything you can ask for the perfect family vacation or a small getaway to sunny Florida. The home offers a top chef kitchen open floor plan, surround sound and a wonderful view of the pool from just about every part of the house.

Jun 23 – 30

R12,155 ZAR per night

Guest favorite

Tiny home in Delray Beach

4.95 out of 5 average rating, 82 reviews

Private Escape; Mini Pool

This super cute tiny home is located in a quiet residential neighborhood. It offers a queen size bed, speedy wifi, full kitchen, bathroom w/ spacious walk-in shower, and 1 smart tv. Simple, cute, clean, minimalist-- yet all of the basic essentials needed for your stay. There's also a private plunge pool on site to cool down and relax. Want to venture out instead?..The beach and downtown area are only 2 miles away! Hurry & book!

May 11 – 18

R2,543 ZAR per night