Holiday rentals with a pool in Delray Beach

4.9 out of 5 average rating, 208 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 🏖

Superhost

4.91 out of 5 average rating, 118 reviews

Luxe Poolside Villas I

Welcome to Delray Beach’s stylish luxe villas. This pool home is perfect for a family or couple’s getaway. This modern villa offers a tranquil residential vibe alongside quick, easy access to the downtown areas and the popular Delray Beach. admire the crisp, contemporary decor or relax in your private patio equipped with BBQ grill and outdoor seating. Inquire about renting all 4 villas together. ALL 4 VILLAS HAVE THEIR OWN PRIVATE PATIO AND HAVE ACCESS TO THE 11,000 sq ft RESORT W/ AMENITIES.

4.98 out of 5 average rating, 131 reviews

Home in Lake Worth

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

Superhost

4.83 out of 5 average rating, 145 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!

4.98 out of 5 average rating, 109 reviews

Waterfront Htd Pool, Spa, Pool Table, Lanai, Canal

Indulge in this luxurious 4BR 2BA haven on a picturesque waterfront property in a prime location in Delray Beach, FL. This spacious getaway offers the perfect retreat from bustling crowds with its trendy design, high-end comforts, and scenic backyard that will leave you in awe. ✔ 4 Comfortable Bedrooms ✔ Open Design Living + Pool Table ✔ Fully Equipped Kitchen ✔ Screened-In Porch ✔ Backyard (Swimming Pool, BBQ, Dining, Dock) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking Learn more below!

4.93 out of 5 average rating, 204 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.

5 out of 5 average rating, 23 reviews

702A Delray Waterfront, Pool, Tiki Hut + Putting G

DELRAY NIGHTLY offers a luxurious waterfront vacation rental in beautiful Delray Beach! Unwind in the heated pool, play on the putting green, relax by the firepit, or dine under the Tiki hut. Inside features a gourmet kitchen, open living space, king beds, and smart TVs in every bedroom. Just 10 minutes from Atlantic Avenue and sandy beaches, with quick access to Boca Raton’s upscale shopping, dining, golf, and nightlife. Your perfect Florida escape awaits—book your dream getaway now!

4.95 out of 5 average rating, 95 reviews

Delray Bali House ~ Heated Pool ~ Sauna ~ Hot Tub

☆ 5% Military and First Responder Discount ☆ Escape to our Bali inspired oasis in the heart of Delray Beach! Immerse yourself in the city's vibrant culture while enjoying the local dining and shopping scene. Take a quick ride to the pristine beach for a fun-filled day of swimming, paddle-boarding, and boating, or head over to Lake Ida for a peaceful fishing trip. Unwind in the tranquil amenity filled backyard. Rejuvenate and make long lasting memories with your loved ones. Welcome!

4.96 out of 5 average rating, 137 reviews

DWTN Delray Pool Home | FREE 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!

4.87 out of 5 average rating, 214 reviews

Condo in Delray Beach

Retro charm studio steps from beach & Atlantic Ave

Charming studio with vintage vibes in a serene location near Atlantic Avenue—just a 2-minute walk to the beach and Opal Grand Beach Hotel. Step into a bygone era, radiating 1950s nostalgia in one of Delray Beach’s most coveted spots. Enjoy the Grove Condominiums' old-world charm, pool, and tropical gardens. Soak in Delray Beach's retro essence with upscale bars, diners, and boutique shops nearby. Embrace classic charm and coastal living in this slice of the '50s.

4.9 out of 5 average rating, 220 reviews

Lux 2 King beds 4 Br2 bath, walk to everything.

Professional Hospitality, sparkly clean, luxurious finishes, organic cotton & down beddings. Teak furniture and a relaxing tub. Relaxing outdoor patio and dining. Only 2 walking blocks from the vibrant Atlantic Ave and shuttle to the beach (no need to drive anywhere!!!). Great for families or a group. No Pets no exception. ABSOLUTELY NO SMOKING- INDOOR and OUTDOORS. **If you are a smoker, kindly, DO NOT consider staying here.