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Holiday Rentals with Pools in Delray Beach

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    Travellers to Delray Beach are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    35 Matching Rentals in Delray BeachView all 71 rentals
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    WONDERFUL 2BED/2BATH UNIT STEPS FROM THE BEACH #31 / 13
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    House in Delray Beach + big pool1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Grove Condominium is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove a single story private residence. Stay a week, a month or longer...and relax :) :) Unit and Space: This One bedroom Unit has a full kitchen and large...
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    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    This idyllic and peaceful home is surrounded by lush tropical landscape. The blue lagoon like pool is a wonderful space to spend a lazy afternoon under the shade of the many palms and verdant foliage. Inside the spaces are spacious, open and airy. The living room looks out to a green tropical...
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    Delray Beach, Florida 33483
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    For lease, 28 night minimum rental, is this 2 bedroom 2 bath, fully furnished and supplied, immaculate condo on the third floor of Building 6 with lake view from master bedroom and patio, located in the Delray Racquet Club Condominium Community in beautiful Delray Beach,Florida. The community is...
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    Delray Beach, Florida 33444
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beautiful 2 Bedroom/2 Bathroom Unit in Delray (#5)1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Reviewed 5 April 2017
    Location, Location Location- can't beat it for this price!The unit was not luxurious (by any means) but it was very good. There were just the two of us with two bedroom and 2...
    Reviewed 29 December 2016
    Our family of 5 enjoyed our stay in unit 5-A, which was not fancy but quite sufficient. We cooked virtually every meal in the tiny kitchen, which saved a lot on expenses, but...
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    About this property
    The Grove is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove is a single story private residence. Stay a week, a month or longer...and relax :) This Two Bedroom/Two Bath Unit includes a full kitchen, living room with two full...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Great Deal 2 bed/2bath Condo (Unit 7)1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 2 April 2017
    Lovely condo. Clean and nicely decorated. Great location. Building has a tons of amenities including doorman, parking garage,workout room and pool.
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    About this property
    Amazing 2 Bedroom/ 2 Bathroom Unit available in the Heart of Delray Beach, FL right off Atlantic Avenue. We are a 2 minute walk away from the Beach and all the restaurants and the nightlife of Delray. Book today according to the availability of the calendar. This Two Bedroom Unit includes a full...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Fabulous location! This 2 bedroom beach hideaway is a short three block walk to the fabulous entertainment center of Atlantic Avenue. Enjoy world class restaurants, fun boutiques and shopping and live weekend bands, then return home with a short walk or take the free Delray Downtowner! This...
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    Delray Beach, Florida 33483
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    WARM & SUNNY SOUTH FLORIDA RENTAL - DELRAY BEACH,1 / 9
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed 10 April 2017
    Alex and his wife were very friendly and made sure we had everything we needed. The amenities in Kings Point are great. Loved the pool and the clubhouse theatre!
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    About this property
    WARM & SUNNY SOUTH FLORIDA RENTAL - DELRAY BEACH, FLORIDA Our beautiful, fully renovated condo (760 sq.f.), is ideally located in sunny South Florida. The nice 1 bedroom, 2 bath unit, and is quite comfortable for an extended stay. We have undergone a complete remodel that features new flooring,...
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    Delray Beach, Florida 33446
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    The Grove is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove is a single story private residence. Stay a week, a month or longer...and relax :) This One Bedroom Unit includes a full kitchen, living room with bathroom. The Unit...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    There’s no lack of places to swim and lounge around at Dover House Resort. A heated outdoor pool sparkles in the sunlight, and a short walk will take you right to the beach, where warm sands hug the Atlantic’s crashing waves. •Eco-friendly updates: The resort earned Green Lodging Designation...
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    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    Pet friendly
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    About this property
    The Grove is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove is a single story private residence. Stay a week, a month or longer...and relax :) This Two Bedroom Unit includes a full kitchen, living room with bathroom. The Unit...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Grove is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove is a single story private residence. Stay a week, a month or longer...and relax :) This One Bedroom Unit includes a full kitchen, living room with bathroom. The Unit...
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    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Satellite TV
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and simple room in a townhouse, newly renovated, close to downtown Delray and beach, private patio, shared kitchen and living room.The room on the second floor, basic furniture, balcony, clean and furnished bathroom. Owner has a cat; can provide with clean sheets and towels, access to...
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    Delray Beach, Florida 33445
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Charming Beach Cottage located in the heart of Delray Beach. Original exposed wood beams, wood floors and loads of charm will make SeaGrape Cottage a family favorite for years to come. Completely updated with modern interior appointments including the kitchen and 2 bathrooms. Ensuite master bath...
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    Delray Beach, Florida 33483
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This fully furnished fourth floor corner unit with two master suites and two baths is loaded with amenities and offers and incredible view of tennis courts!Wait till you see the newly remodeled kitchen with granite counter tops, new refrigerator, new dishwasher, microwave, coffee maker. toaster....
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    Delray Beach, Florida 33444
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    A sophisticated modern oasis in the center of the city. Private, lush, landscaped grounds surround outdoor seating areas and full-size pool with spouting water feature. Volume interior spaces with luxury finishes set Delray Modern apart! With 3,776 total sf living space, this stunning home is...
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    Delray Beach, Florida 33483
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous private home completely renovated. 2.5 miles to beaches and less than 1 mile to downtown Delray's restaurants and shopping district. Inside of the exclusive gated Seagate Country Club on Atlantic Avenue. This is the only gated community this close to the beach. Very safe and quiet...
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    Delray Beach, Florida 33445
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    30 DAY MINIMUM RENTALS ONLY PLEASE Minimum booking for January to March is 90 days. This home was refurbished in November 2012 with new furniture, three large flat screen T.V.'s including a 70 inch in the living area, a 46 inch in the master bedroom and a 46 inch in the second bedroom. Also...
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    Delray Beach, Florida 33446
    Holiday Rental House - 3 Bedrooms, Sleeps 7
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    Tahiti Cove -Waterfront Condo-Walk to Everything1 / 19
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Waterfront
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    About this property
    Two, charming, updated condos in a unique, quiet, beautiful, tropical intracoastal waterfront property .Conveniently located in one of the few original Delray Beach communities, with almost everything in walking distance. Sit by the heated pool and watch the boats go by on a wide expanse of the...
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    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    This Exquisite Spanish style waterfront 5 bedroom situated on a point lot steps from the beach and directly on the intercostal waterway. The property has 7500 sq. feet and 5 bedrooms and attached baths. ​ A large dock surrounds the property which has all the amenities of the multi-million dollar...
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    Delray Beach, Florida 33483
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    About this property
    Amazing Penthouse Condo in Delray Beach! Perfect for entertaining. Key West Resort style living all within minutes of the water & Atlantic Ave. This 2 Bedroom, 2 & 1/2 Bath, 2 story condo Penthouse is located in a private community complete with oasis pool, putting-green & basketball court all at...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This luxury newly renovated 2 bedroom 2 bath unit is just beautiful. With all state of the art amenities, you'll feel like your right at home when away on vacation. This is the best unit in the complex! The unit has a pull out couch which can sleep 2 additional people (extra charge of course) Queen...
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    Delray Beach, Florida 33483
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    The Grove Condominium is a quiet retreat in the heart of Delray Beach! A tropical setting steps from the beach, shopping and dining. The Grove a single story private residence. Stay a week, a month or longer...and relax :) :) Unit and Space: This one bedroom Unit has a full kitchen and large...
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    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Condo in 55+ California style fully furnished 2 b/r, 2 bath, eik, l/r, d/r, screened in covered patio. Clubhouse with pool, tennis, shuffleboard. Condo clean, fully equip kitchen with new microwave. Washer/dryer in unit. . New Queen mattress in master. Sofa bed in 2nd b/r. Near shopping &...
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    Delray Beach, Florida 33484
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Avalable only for 01 october through 31 decembre 2017. This nice villa is located 40 min North of the Ft-Lauderdale airport. 1,200 sq feet.. (110 m carré) under air conditionned. Two spacious bedrooms with lots of storage. The Master has its on bathroom. Newly furnished in a beach style trend....
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    Delray Beach, Florida 33484
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
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    Pet friendly
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    About this property
    This beautiful, spacious and fun home is located in Historic Downtown DelRay Beach, Florida, only a 4 minute drive to Atlantic Ave. with all the delicious restaurants, cafes, fun shops and beautiful beach. There are many fun events and activities in Downtown DelRay, very close to the home. It's in...
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    Delray Beach, Florida 33444
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Completely remodeled modern condo with brand new furniture. Lake view, new fully equipped kitchen and bathroom, washer and dryer, flatscreen TV's, wi-fi internet in the unit. Delray Racquet Club is a resort style community with 2 swimming pools, spa, gym and tennis courts. Cable TV, water and...
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    Delray Beach, Florida 33444
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 storey , 2800 square foot townhouse in Delray Beach Absolutely Gorgeous townhouse with pool in beautiful Delray Beach. This unit has sun all afternoon ! every upgrade that the developer has offered. High-end furniture and artwork finish this unit and make it perfect for a tenant's vacation!!!...
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    Delray Beach, Florida 33483
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    About this property
    Spacious Oasis With Oversize Heated Pool And Spa, Large Yard 4 Bedroom, 2.5 Bathroom, With Oversize Pool The perfect getaway house to relax and enjoy while you are away from your own home. This home is suitable for a large family, children and their fur-baby. Located in a quite neighborhood and...
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    Delray Beach, Florida 33445
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    Pet friendly
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    About this property
    Ocean Manor is located across the street from the Atlantic Ocean and beautiful coral sand beaches of Delray Beach. It is easily accessible from all local and International airports the closest being Palm Beach International. Atlantic Avenue is only a mile away and home to the cities best...
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    Delray Beach, Florida 33483
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 2 days ago
    The place was really clean and updated nicely. It was a great location Restaurants and beach very close. Definitely would rent again!!
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    About this property
    Located just minutes from Beaches and Downtown Delray, A top winter destination on the east coast of Florida. Countless activities, world-renowned restaurants, galleries, shopping, entertainment and much more. This private villa offers a clean, comfortable and laid back community. Easy ground floor...
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    Location Information
    Delray Beach, Florida 33445
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Great location in walking distance of downtown Delray on so ocean blvd close to restaurants including famous Boston's on the beach also nice pool and free parking. a condo sleeps 4 best location in Delray beach. This comm take a break from the beach and go across the road to Bostons it is known...
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    Location Information
    Delray Beach, Florida 33483
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATED in Delray Beach Florida. BOATER'S JET SKI'S BEACH GOERS, PET OWNERS, POOL AND SPA this is it! enjoy the total Florida lifestyle sit by the pool look at the boats go by on the intracoastal. Dine in one of the fabulous restaurant cafes on ATLANTIC BOULEVARD. Shop in BOCA TOWNCENTER...
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    Location Information
    Delray Beach, Florida 33483
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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