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, 214 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.

Feb 7 – 14

G$26,493 GYD per night

Guest favorite

Home in Boynton Beach

4.89 out of 5 average rating, 159 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!

Jul 11 – 18

G$26,967 GYD per night

Guest favorite

Guest suite in Lake Worth Beach

4.97 out of 5 average rating, 275 reviews

Quiet Private Studio w/Pool for One Guest

My Quiet/Private & Beautiful Studio w/ pool is perfect for a single nonsmoking petless professional, golfer, nurse/med student on rotations in Palm Beach centrally located to all area hospitals, the county's many diverse golf courses & the Wellington equestrian community. Private Entrance w/ illuminated off street parking spot, large brand new stone embellished bathroom, granite countertop, mini Kitchen w/ fridge, microwave, and coffee are just a few upscale ammenities inherrent in my place.

Aug 20 – 27

G$21,307 GYD per night

Guest favorite

Condo in Delray Beach

4.84 out of 5 average rating, 167 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.

Aug 28 – Sep 4

G$27,036 GYD per night

Guest favorite

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 325 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.

Jun 23 – 30

G$27,369 GYD per night

Guest favorite

Home in Delray Beach

4.91 out of 5 average rating, 174 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 11 – 18

G$72,928 GYD per night

Guest favorite

Condo in Boynton Beach

4.84 out of 5 average rating, 115 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.

Sep 25 – Oct 2

G$22,014 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.

Sep 2 – 9

G$28,259 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!

Aug 6 – 13

G$50,403 GYD per night

Guest favorite

Home in Delray Beach

4.97 out of 5 average rating, 66 reviews

Delray Bungalow/ 3BR 2BA East Delray Pool Home

Spacious and elegant, this three-bedroom two bathroom home is located in Chevy Chase — one of Delray Beach's premier, top-rated neighborhoods. Here you’ll have the best of both worlds— a central location close to downtown combined with the exclusive privacy and peace of a classic South Florida home. Enjoy pristine cleanliness, complete safety and security, and world-class customer service. Look no further— you’ve found your new home base in Delray Beach.

Jul 27 – Aug 3

G$81,523 GYD 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!

Jul 6 – 13

G$28,127 GYD per night

Superhost

Guesthouse in Boynton Beach

4.89 out of 5 average rating, 153 reviews

COCONUT CASITA {Delray Beach | Boynton Border}

COCONUT CASITA: Detached studio cottage in east Boynton Beach (Boynton Beach / Delray Beach border) with Old Florida charm. 2 miles to nearest beaches and downtown Delray. 3 miles from Ocean Ave waterfront dining in Boynton Beach. Good for couples, solo adventurers, and small families... Details: Furnished, Cable/Internet included, Queen size canopy bed, Twin/single sofa bed, Full kitchenette, Parking, Private entrance.

Dec 20 – 27

G$33,539 GYD per night