Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Narrow Results

Wailea: Villas, Condos & More (32)

  • 1 - 30 of 32
    • 2 BR
    • 2 BA
    • Sleeps 6
    Request to Book View Details
    24 hrs Confirmation within 24 hours
    Special Offer! SUPER SUMMER SAVINGS - ONLY $169/night!! June 1 - July 31
      • 2 BR
      • 2 BA
      • Sleeps 6
      14
      Request to Book View Details
      24 hrs Confirmation within 24 hours
      Special Offer! >>>---------> $20 OFF SEPTEMBER OPEN DATES (while they last) April 24 - May 22
        • 2 BR
        • 2 BA
        • Sleeps 6
        31
        Special Offer! $145/NT DISCOUNT MAY 12 TO MAY 22 May 12 - May 22
          • 6 BR
          • 6 BA
          • 3 HF BA
          • Sleeps 12
          Special Offer! ** INTRODUCTORY SPECIAL! SAVE $500/night OFF! ** April 12 - November 18
            • 3 BR
            • 2 BA
            • Sleeps 6
            4
            Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF OCEAN VIEW VILLA! May 1 - June 10
              • 4 BR
              • 3 BA
              • Sleeps 8
              2 Reviews
              Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF OCEAN VIEW VILLA! May 21 - June 4
                • 3 BR
                • 3 BA
                • Sleeps 6
                2 Reviews
                Special Offer! ** LAST MINUTE SALE! SAVE $100/night OFF ocean view villa ** April 30 - May 21
                  • 3 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 6
                  Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF plunge pool villa! May 1 - May 21
                    • 3 BR
                    • 3 BA
                    • 1 HF BA
                    • Sleeps 6
                    1 Review
                    Special Offer! ** LAST MINUTE DISCOUNT! SAVE $100/night OFF! ** May 16 - May 26
                      • 3 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 6
                      2 Reviews
                      Special Offer! LAST MINUTE DISCOUNT! SAVE $200/night OFF plunge pool villa May 15 - June 10
                        • 3 BR
                        • 3 BA
                        • 1 HF BA
                        • Sleeps 6
                        2 Reviews
                        Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF plunge pool villa! April 30 - May 26
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                          3
                          Special Offer! ** SPRING SPECIAL! Save $300/night OFF ** April 28 - May 14
                            • 3 BR
                            • 2 BA
                            • Sleeps 6
                            Special Offer! ** LAST MINUTE DISCOUNT! SAVE $100/night OFF! ** May 23 - June 2
                              • 3 BR
                              • 3 BA
                              • 1 HF BA
                              • Sleeps 6
                              Special Offer! ** LAST MINUTE DISCOUNT! SAVE $100/night OFF! ** April 30 - May 19
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                1 Review
                                Special Offer! LAST MINUTE DISCOUNT! Save $100/nt OFF OCEAN VIEW PENTHOUSE May 1 - June 10
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  1 Review
                                  Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF OCEAN VIEW VILLA! May 22 - June 10
                                    • 3 BR
                                    • 3 BA
                                    • Sleeps 6
                                    3
                                    Special Offer! LAST MINUTE DISCOUNT! Save $100/nt OFF OCEAN VIEW PENTHOUSE May 1 - May 25
                                      • 3 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF OCEAN FRONT VILLA! May 8 - May 22
                                      Special Offer! ** INTRODUCTORY SPECIAL! Save additional $200/night OFF! ** April 27 - May 28
                                        • 3 BR
                                        • 3 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        1 Review
                                        Special Offer! LAST MINUTE DISCOUNT! Save $100/night OFF ocean view villa! May 17 - June 10
                                          • 2 BR
                                          • 2 BA
                                          • Sleeps 6
                                          14
                                          Request to Book View Details
                                          24 hrs Confirmation within 24 hours
                                          Special Offer! Best Discounted Summer rates May 14 - August 31
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            12
                                            Request to Book View Details
                                            24 hrs Confirmation within 24 hours
                                            Special Offer! FREE CLEANING!!! July 1 - December 31
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Request to Book View Details
                                              24 hrs Confirmation within 24 hours
                                              Special Offer! 10% OFF JUNE AND JULY BOOKINGS!!! June 12 - July 22
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 6
                                                21
                                                Request to Book View Details
                                                24 hrs Confirmation within 24 hours
                                                Special Offer! 2016 SPECIAL DISCOUNT RATES!! RESERVE NOW WHILE DATES LAST!! May 2 - December 31
                                                  • 2 BR
                                                  • 2 BA
                                                  • Sleeps 6
                                                  11
                                                  Request to Book View Details
                                                  24 hrs Confirmation within 24 hours
                                                  Special Offer! LATE SPRING SPECIAL!! $150 a night!! April 17 - June 30
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    6
                                                    Request to Book View Details
                                                    24 hrs Confirmation within 24 hours
                                                    Special Offer! NEW Special $100 Less/Night - Now through October - Book Now April 22 - October 15
                                                      • 1 BR
                                                      • 2 BA
                                                      • Sleeps 4
                                                      Request to Book View Details
                                                      24 hrs Confirmation within 24 hours
                                                      Special Offer! Value Season Rates May 11 - June 30
                                                        • 3 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        3
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                        Special Offer! $100 Off/Night - NEW Rates through October - Keawakapu Beach April 22 - October 15
                                                          • 3 BR
                                                          • 3 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          6
                                                          Special Offer! Jump Into Summer Early ~~ $599 per nt* Special May 22 - June 23
                                                            • 2 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            32
                                                            Special Offer! Wow! Only $550 per night ($145/night discount--20% off) May 1 - June 16
                                                            • 1 - 30 of 32
                                                             

                                                            Recent Wailea Reviews

                                                            Very Nice Property

                                                            4 of 5
                                                            I stayed here with my wife and 3 boys for 10 nights over spring break. There is more than enough room for my 17, 15 and 11 yr olds. I Love the property and convenience of the shops. We have stayed at the Wailea Beach Villas before and this unit is probably a little nicer than others we have stayed at. There are two pools at this resort. The nicer of the two overlook the ocean but it does not allow children under 18. The second pool is also very nice next to the penthouse suites so you could be on your lani and overlook your young kids in the pool. The only disappointment was we were promised a late departure (we had a 10:00 pm flight) if available when I booked the condo 6 months earlier. We were told the day before that they were not able to accommodate the request even though the unit was empty for the next two nights. They would have had to change the cleaning crews we were told. You can't claim to have Four Seasons Service and then not accommodate a simple request. If someone was in the condo that night I would completely understand. We have already booked the Wailea Beach Villas again next March but are staying in a different unit with a different management company. I would use Tropical Beach Villas again if they had a condo I specifically wanted to rent, but I would certainly look at all of my options.
                                                            • Submitted: Apr 14, 2016
                                                            • Stayed: Mar 2016

                                                            Wailea Sunset Bungalow

                                                            5 of 5
                                                            My husband and I spent more than a week at WSB with our teenage daughter and her friend. While there is only one bath, there are three words to describe this place: location, location, location! Waterfront, in Wailea, but really a world away as it is so private. Perfectly equipped, attractively decorated, we only wish we could have stayed longer!
                                                            • Submitted: Apr 7, 2016
                                                            • Stayed: Mar 2016

                                                            Spectacular.

                                                            5 of 5
                                                            I've rented several nice properties over the years, but I've never seen my family so impressed as they were with this one. "How did you find this?" They kept asking. Bring your binoculars to watch the whales from the patio. If you don't want to use their incredible, very well-stocked kitchen, don't go out to eat. Order takeout and enjoy it from the balcony. This is one of the finest properties I've ever rented. Most importantly, though, is the attention to the needs of a traveler, and the "extras" around the house: batteries; games; movies; umbrellas; towels for the beach; extra towels for the Road to Hana; several coolers to pack a picnic; six robes (we took a family picture to prove it); bidets with heated toilet seats (that one never seems to get marketed!); better grill and grilling equipment than I own myself; private elevator; extremely convenient parking spot; laundry stuff; office equipment. It's in a wonderful location. You're actually closer to the ABC Store than you are to the beach. But that's also a downside. The villa is quite a bit further from the beach than I expected, and a lot of it is on stairs. It's at least a 5 to 7 minute walk, which gets old after a while. It's not practical to go back to the villas for a Coke once you're on the beach, so take advantage of their coolers. I always walked to the beach with a backpack, even if I thought I wasn't staying, because invariably one of the kids would want to get in, and I didn't want to walk back for a book, etc. Minor quibbles would be the entertainment system. We couldn't play our iPhone music because their connectors were out of date. Also, my wife and I had planned to binge-watch Netflix because I was under the impression they had an Apple TV. They didn't. The living room had a DVR, but not the Master. Once I had to reconnect some of their HDMI cables, which had fallen loose. BUT the mall had a Redbox, and we had a great time watching the movies we rented. The large TV was beautiful. (I know, I know. We didn't go to Hawaii to watch TV...but still. Hopefully, they'll read this and let us watch Netflix next time.) I've rented probably over twenty different properties over the years for family vacations. Usually high end stuff, as the family can only rarely take off together. This is easily one of the two best I've ever been in. And easily the greatest deck and living room I've ever rented.
                                                            • Submitted: Mar 22, 2016
                                                            • Stayed: Mar 2016