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, 90 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

Home in Delray Beach

4.96 out of 5 average rating, 73 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.

Guest favorite

Guest suite in Boca Raton

4.94 out of 5 average rating, 33 reviews

Boca Studio with Relaxing Screened Patio Oasis

Discover Boca Raton's charm from our serene studio, steps away from a public golf course. Offering a queen bed, private patio and a kitchen with modern amenities including a dishwasher. Perfect for beach trips, we provide chairs, umbrella, and towels. Ideal for families, with a car seat, toys and crib on request. Just 7 miles to the beach, immerse in local dining and beachside allure. High-speed Wi-Fi and a dedicated workspace ensure a blend of relaxation and productivity & large community pool.

Guest favorite

Home in Delray Beach

5 out of 5 average rating, 43 reviews

Heated saltwater pool | close to beach & the Ave

Welcome to our charming getaway near Boca Raton! Enjoy the convenience of early check-in and late check-out (subject to availability). Perfect for families, friends, or remote work: features 2 stylish bedrooms, 2 bathroom, a open living area with a 75-in smart TV and the spacious backyard with a heated saltwater pool. Atlantic Dunes Park - 6 min drive Delray Downtown/Atlantic Ave - 7 min drive Boca Raton/Mizner Park - 11 min drive Book For Lasting Memories In Delray Beach—See Details Below!

Guest favorite

Home in Lake Worth

4.98 out of 5 average rating, 111 reviews

Tranquil Vibes ~ Pet Friendly Private Pool Home

Welcome to our cozy pool home with screened porch, deck w/ remote control lighting of cabana for evenings. Grill, tropical fruit trees, plants & private fenced yard. Coastal cottage decor mixing vintage finds in newly remodeled space. Neighborhood is peaceful w/ close drive to beaches, restaurants, golfing, parks & shopping. Each bedroom has cooling mattress pads & ceiling fans. Pets welcome! Beach chairs, cooler, bikes, beach umbrella, pool floats, yoga mat, games/books-.Long stays welcome

Guest favorite

Condo in Delray Beach

4.86 out of 5 average rating, 192 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

Home in Delray Beach

4.93 out of 5 average rating, 172 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, 183 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, 376 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, 119 reviews

Delray Beach House | Pool | Near Atlantic Ave

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

4.91 out of 5 average rating, 23 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.