Holiday 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.

0 of 0 items showing

1 of 3 pages

Guest favourite

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.

4 – 11 Feb

$1,596 AUD total

Guest favourite

Condo in Delray Beach

4.85 out of 5 average rating, 168 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.

6 – 13 Nov

$1,715 AUD total

Guest favourite

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.

29 July – 5 Aug

$4,642 AUD total

Guest favourite

Guesthouse in West Palm Beach

4.97 out of 5 average rating, 326 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.

18 – 25 Oct

$1,736 AUD total

Guest favourite

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.

18 – 25 Oct

$3,821 AUD total

Guest favourite

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.

28 Sept – 5 Oct

$1,625 AUD total

Guest favourite

Home in Delray Beach

4.95 out of 5 average rating, 42 reviews

Dreamy Oasis w Pool Steps Off Atlantic Ave

NEWLY LISTED -- Casa Atlantica is a 3-bedroom, 3-bathroom luxury home located in the core of Delray Beach, Florida. Close to the vibrancy of Atlantic Avenue yet nestled in a private historical neighborhood, Casa Atlantica is the perfect getaway. This Modern Bermudian style home offers everything -- beautiful, professionally designed interiors and expansive outdoor living with saltwater pool, dining patio and two covered loggias. Enjoy the best of Delray Beach living at Casa Atlantica!

17 – 24 Oct

$8,987 AUD total

Guest favourite

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.

16 – 23 Nov

$1,686 AUD total

Superhost

Condo in Boynton Beach

4.86 out of 5 average rating, 63 reviews

Condo *Luxurious Resort- Style* & garage parking

Our Condo is located in a luxurious and modern, resort style complex that offers all the amenities of a resort. You will have the entire Condo to yourself. The location is perfect with the beach within a 5 minute drive at exactly 1 mile and steps to several restaurants and a marina where you can rent jet skies, wave runners, boats or take a fishing trip for the day. The Boynton Beach Mall is a 10 minute drive as well as Atlantic Ave in Delray Beach and beautiful Palm Beach Island.

10 – 17 May

$1,650 AUD total

Guest favourite

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!

21 – 28 May

$3,144 AUD total

Guest favourite

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!

20 – 27 May

$1,706 AUD total

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.

19 – 26 Oct

$1,920 AUD total