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Vacation Rentals in Wailea, HI

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All 229 Rentals in Wailea
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$356
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$199
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
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$190
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 2
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Also consider
Elua Village # 701 - Luxury 2b/2b with Ocean View!
2 Bedrooms, sleeps 5
$395 - $485 / night
Ekahi10E- OceanViews on Lower Village Greenbelt
1 Bedroom, sleeps 2
$295 - $360 / night
Modern Stylish Condo, Designer Touches Throughout!
2 Bedrooms, sleeps 6
$185 - $275 / night
Partial Beach Ocean View Remodeled Ekahi Condo 18E
1 Bedroom, sleeps 4
$265 - $355 / night
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$369
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$190
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1 / 11
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2 Bedrooms, 3 Bathrooms, Sleeps 8
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$695
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1 / 44
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3 Bedrooms, 4 Bathrooms, Sleeps 10
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5 of 5 stars Reviewed April 12, 2014
Our first trip to Maui, Hawaii for our Daughters wedding. We were a family of 8 (including grandparents).Plenty of room,Condo is immaculate, amazing, beautiful, photo's were...
5 of 5 stars Reviewed December 30, 2013
Upon our arrival, we immediately knew we hit the jackpot! The spacious condo was beautiful and full of every necessity needed for our vacation. The views from the lanai were...
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$290
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1 / 17
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$195
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1 / 13
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1 Bedroom, 2 Bathrooms, Sleeps 2
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5 of 5 stars Reviewed May 14, 2014
We travelled to Maui in March, stayed for two weeks in a lovely condo at Grand Champions, Wailea. We went with 10 other friends, who also rented condos there. The manager...
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$210
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1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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4 of 5 stars Reviewed November 11, 2014
I was a little worried to about renting this condo as it had no reviews, but it was better than I expected. The condo is clean, very nicely decorated and has a great covered...
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$1,250
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1 / 22
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4 Bedrooms, 3 Bathrooms, Sleeps 10
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$215
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1 / 13
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$195
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1 / 15
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$149
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1 / 25
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$295
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1 / 7
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1 Bedroom, 2 Bathrooms, Sleeps 3
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From
$995
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1 / 32
3 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$695
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1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$200
Per Night
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1 / 14
1 Bedroom, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed November 9, 2014
We had a great week at Wailea Ekahi, enjoying both the unit we rented and the location of the Ekahi resort. Would highly recommend for a couple or a family with young children...
4 of 5 stars Reviewed August 17, 2014
Skip and Mickey were fantastic from the beginning. They have taken special care to stock the condo with everything you might need for a relaxing, fun trip to the beach. From...
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$240
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1 / 21
1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$115
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1 / 14
Studio, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed October 1, 2013
Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
5 of 5 stars Reviewed September 29, 2012
We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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From
$130
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1 / 25
1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed June 23, 2014
Condo was very clean and with chocolates upon arrival. Beautiful island décor and kitchen was well stocked with basics to prepare meals. Plenty of furniture to store your...
5 of 5 stars Reviewed June 21, 2014
We loved very minute of our stay in the "Secret Garden" apartment. The property is spotlessly clean, well-equipped and beautifully furnished. We enjoyed breakfasts on the lanai...
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$595
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed November 22, 2012
My mother, wife, and I stayed here from Nov. 11th till Nov. 16th, 2012. This is a lovely and nice place you should definately consider staying when making a trip to Wailea, Maui...
5 of 5 stars Reviewed January 12, 2012
My thank you note to the owners: I just want to say thank you for opening up your Maui home to fortunate people such as us. Your home there is lovely! You did a beautiful job...
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$250
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1 / 21
1 Bedroom, 2 Bathrooms, Sleeps 5
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5 of 5 stars Reviewed September 13, 2014
We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
5 of 5 stars Reviewed July 24, 2014
My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean...
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$345
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1 / 37
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed July 25, 2014
Beautiful ocean view from balcony, living room and kitchen. My family loved unit # 306. Condo was better than photos. Very comfortable for a family of 5. Beds were comfortable...
5 of 5 stars Reviewed July 20, 2014
My husband, daughter, sister and brother-in-law rented Unit 306 at Polo Beach Club in Wailea, Maui. It was a wonderful experience! We were on the 3rd floor with a corner unit that...
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$250
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1 / 8
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1 Bedroom, 2 Bathrooms, Sleeps 5
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4 of 5 stars Reviewed February 27, 2013
My husband and I stayed in this unit for 3 weeks another couple joined us for 2 weeks. The owner was easy to work with and provided all the needed information to make our stay...
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$115
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1 / 7
1 Bedroom, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed January 25, 2014
My partner and I came to Maui to run the Maui Oceanfront Marathon. We had booked a room at the Marriott for which the marathon had a room block. However, because we wanted to...
5 of 5 stars Reviewed February 3, 2013
Three of us (wife, toddler girl and myself) rented this place in early January. The condo is just the right size for us. We love the location. It's in an upscale area of Maui...
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$900
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1 / 20
3 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed August 18, 2014
From the moment we arrived with the greeter to the accommodations, the grounds and the concierge Tracy, it was perfect. Great condo, stocked better than our home, beautiful...
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From
$700
Per Night
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1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$895
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1 / 42
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed August 24, 2014
We were so thrilled with our stay at unit J205 Wailai Villas. From the moment we arrived and were met with a lovely welcome basket, we felt right at home. It was a perfect amount...
5 of 5 stars Reviewed August 13, 2014
This place was incredible. It was modern, clean , and had a great view. The facility is beautifully maintained and the service onsite is first class.THe beach wand the poo;s are...
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From
$755
Per Night
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1 / 15
3 Bedrooms, 4 Bathrooms, Sleeps 8
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From
$250
Per Night
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1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed April 7, 2013
We spent 8 wonderful nights in Grand Champions. Location was perfect, 5 minutes to Big Beach and Shops at Waliea. Condo was clean and tons of space. We had two teenage girls and...
5 of 5 stars Reviewed January 27, 2012
We stayed here in early December 2011 for 12 nights. There were 4 adults and 2 children ages 8 years and 21 months. The property was perfect and had everything for our needs...
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From
$450
Per Night
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1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed November 13, 2014
From the moment we walked in the door, we were in love with our condo. The furnishings were perfect, the view was spectacular, the beach was fabulous, and the management was very...
5 of 5 stars Reviewed August 2, 2012
The place, location, beach was perfect for my family. We had three little kids and it was ideal. I will be back.
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From
$290
Per Night
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1 / 19
1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$170
Per Night
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1 / 23
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1 Bedroom, 2 Bathrooms, Sleeps 4
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1 of 5 stars Reviewed September 27, 2014
I booked this condo in July as 3 of us are attending a conference. I was notified that my final payment was due, which I paid promptly. On Mon. I received a notification that my...
5 of 5 stars Reviewed April 3, 2014
We ran across this particular condo because we needed to fill in 3 additional days on our recent stay in Maui. The only regret is we didn't know about it earlier. The condo itself...
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From
$340
Per Night
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1 / 18
1 Bedroom, 2 Bathrooms, Sleeps 3
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4 of 5 stars Reviewed October 24, 2014
What a lovely appointed condo with so many wonderful attributes. We found the unit in perfect condition with comfy beds & large bathooms.The Lanaii was a great size & we had...
5 of 5 stars Reviewed July 26, 2014
Just returned from Maui and Wailea Ekahi 7G delivers everything promised. The unit is beautifully decorated and has every imaginable amenity. The kitchen is extremely well...
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$159
Per Night
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1 / 31
1 Bedroom, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed April 23, 2014
I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
5 of 5 stars Reviewed September 10, 2013
I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
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$395
Per Night
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1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed September 21, 2014
I have been to Ekahi for 5 years, staying in other condos. None compare with this one. Stunning views of the vegetation, ocean, and small pool. The condo is very cozy and has...
5 of 5 stars Reviewed July 18, 2014
We enjoyed our stay at this condo. It is nicely furnished and the owners supplied amenities to make our beach time much more pleasant. They also supplied numerous books about the...
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From
$4,500
Per Night
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1 / 21
4 Bedrooms, 5 Bathrooms, Sleeps 8
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From
$585
Per Night
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1 / 24
3 Bedrooms, 4 Bathrooms, Sleeps 8
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From
$300
Per Night
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1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 8
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$250
Per Night
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1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Suitability

  • Wheelchair access (16)
  • Elder access (60)
  • Suitable for children (41)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (190)
  • Internet (183)
  • Air Conditioning (157)
  • Other outdoor space (146)
  • All pools (142)
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Book Online(95)

Suitability

  • Wheelchair access (16)
  • Elder access (60)
  • Suitable for children (41)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (190)
  • Internet (183)
  • Air Conditioning (157)
  • Other outdoor space (146)
  • All pools (142)
  • View all amenities
Wailea Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.