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Carefree Holiday Rentals with Pools

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    Travellers to Carefree are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    18 Matching Rentals in CarefreeView all 20 rentals
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    2 Bedroom Casita in a golf resort in Carefree, AZ1 / 32
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    NEW LISTING! Southwest charm w/saltwater pool & pool spa at Boulders Resort1 / 47
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Patio
    • Grill
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ironwood Retreat Discover an enchanting desert oasis when you escape to this elegant North Scottsdale home, a light-filled Arizona retreat with a private swimming pool, an expansive garden terrace with an outdoor fireplace, and a built-in grill. Its luxurious details even include a two-sided gas...
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    Carefree, Central Arizona 85266
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mountain Views and Peaceful Setting in Carefree1 / 24
    (8)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Patio
    • Hot Tub
    • Mountain Views
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2016
    Absolute perfect place to stay in the Carefree/Desert Mtn area....Property has great amenties and very comfortable ! Owner is a tremendous person that made our stay easy as...
    Reviewed 13 October 2016
    We really enjoyed our stay at the Villages at Carefree. The unit was large and comfortable, the pool was excellent, and the location was close to restaurants and attractions...
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    About this property
    Two bedroom, first floor townhome located in gated, secure community. Enjoy the year-round heated pool with whirlpool, putt on the nearby putting green, or enjoy hikes to nearby Carefree and Cave Creek. Located near the foothills,the area is peaceful yet allows you the flexibilty of visiting...
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    Location Information
    Carefree, Central Arizona 85377
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Troon North 112 Spend your next vacation in Scottsdale at this gorgeous, three-bedroom home with a furnished patio, private pool, all just minutes from golf, parks, shops, and more. Visiting golfers have several options to choose from including the top-rated Troon North Golf Club, just two miles...
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    Carefree, Central Arizona 85262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautifully updated townhome with shared pools/hot tub, golf & tennis!1 / 52
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Grill
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2019
    This is a lovely home at the end of a road at the resort, it’s quiet and looks out to the mountains beyond. The home has virtually everything necessary to enjoy your stay. A...
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    About this property
    Boulders Villa This Pueblo-style townhome boasts resort amenities such as shared pools and a hot tub, golf, and tennis on-site, as well as restaurants and a spa. This updated space offers contemporary furnishings and a gorgeous outdoor dining area! What’s nearby: Just northeast of Phoenix,...
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    Location Information
    Carefree, Central Arizona 85266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pinnacle Peak Find a calming desert retreat at this three-bedroom North Scottsdale home, a dog-friendly escape with a private pool, a beautiful backyard patio with a firepit, and a wonderful location for hiking, relaxing, and seeing the local sights! This home is located in North Scottsdale,...
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    Location Information
    Carefree, Central Arizona 85255
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa de Clarita Soak in the southwest vibe at this fresh and modern home. The open concept layout makes mingling easy, and you can swing open the French doors to view the glorious back yard sunsets beyond the private pool and pool spa. This rental is located within a beautiful, gated community that...
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    Location Information
    Carefree, Central Arizona 85266
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Legends Retreat Make this stunning, secluded six-bedroom home in Scottsdale yours and revel in amenities like a private pool, lavish backyard oasis - including an outdoor kitchen - jetted tub, and a secret room! This rental is on an acre boasting mature saguaro cacti and palm trees, a circular...
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    Location Information
    Carefree, Central Arizona 85255
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Santa Catalina Estate This luxury home sits on a 1.3-acre lot and has everything you need for an unforgettable getaway and then some! Inside, this opulent, 6,900-square-foot home has a theatre room, office space, two refrigerators, and multiple fireplaces. There's plenty of dining space for...
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    Location Information
    Carefree, Central Arizona 85255
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let us help create exciting memories and have more fun when you stay with us by providing FREE ADMISSION to some of the area's top attractions each and every day including: - Golf at Starfire Golf Club - Heard Museum - OdySea Aquarium - Escape Room (Lockdown) **Please note this Free Fun package...
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    Location Information
    Carefree, Central Arizona 85255
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Secure Parking
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Terrace
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful resort-style condominium Suite has a large bedroom with two queen beds, cable TV and an adjacent terrace. The living area with its desk, futon couch and refrigerator, shares the terrace allowing easy outdoor enjoyment of the Sonoran Desert . The luxurious bathroom has a full bath,...
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    Location Information
    Carefree, Central Arizona 85377
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private home is conveniently located in Carefree, AZ, surrounded by 20 acres of land preserve. Totally private! This is a residence, not a villa or condo. Please contact me with any question. I am hoping to make your vacation personal and to appease your needs. I manage my own home, not...
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    Location Information
    Carefree, Central Arizona 85377
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    • Grill
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your dream desert destination awaits at this 5BR/3BA luxury villa. Surrounded by stunning desertscape, the immaculate indoor/outdoor entertaining space offers breathtaking and expansive views. Host a poolside cookout with your friends and family. Make use of the outdoor kitchen, float in the...
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    Location Information
    Carefree, Central Arizona 85262
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated community condo on first floor with no stairs or steps with 2 spacious bedrooms and bathrooms (2100 sq feet or 195 sq Meter) and with a patio out of every room. Access to community pool & jacuzzi and club house which is walking distance within gated community. This Condo is located near both...
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    Location Information
    Carefree, Central Arizona 85377
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Upscale Southwestern style, stunning mountain vistas and a gourmet fully equipped kitchen are just some of the fantastic amenities that this Carefree townhome for 4 guests has to offer! The 2-bedroom, 2-bathroom vacation rental features a furnished terrace and access to a community pool and hot tub...
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    Location Information
    Carefree, Central Arizona 85377
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your dreamy desert getaway begins at this Scottsdale vacation rental nestled in the McDowell Mountain Range in a gated community. This 4-bedroom, 3-bath home accommodates 8 guests and boasts 3,230 square feet of tastefully ornamented living space with a private outdoor oasis adorned with a pool,...
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    Location Information
    Carefree, Central Arizona 85262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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