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

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

Home in Delray Beach

4.96 out of 5 average rating, 92 reviews

Charming House "B"

Charming house. Located in quiet residential neighborhood. 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. Plunge pool (4 ft deep) located on the property for your relaxation! Access to plunge pool is available to both tiny houses on the property-- not a community or public pool. Beach and downtown (several shops and eateries) 5 minutes away. Hurry & book!

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.

Guest favorite

Cottage in Delray Beach

4.92 out of 5 average rating, 26 reviews

Historic cottage private pool walk to beach

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.

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

Home in Delray Beach

4.92 out of 5 average rating, 184 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.

Guest favorite

Guesthouse in Flamingo Park

4.97 out of 5 average rating, 382 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.

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

Villa in Delray Beach

4.92 out of 5 average rating, 24 reviews

Red Palm Villas

Step into your very own oasis at this incredible property! Whether you're a dedicated yogi, an urban explorer, or simply someone seeking a sense of community and inner peace, you've found your haven here. With a dedicated Zen Den, lush gardens, and an atmosphere that practically exudes "namaste," this place is the ultimate retreat for those in search of balance and serenity. Embrace the harmonious vibes and make this your urban escape where tranquility meets urban exploration.

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

Guesthouse in Boynton Beach

4.89 out of 5 average rating, 154 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.