Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartment
Boat
Bungalow
Cabin
Castle
Chalet
Condo
Cottage
Estate
Farmhouse
Hotel
House
Lodge
Studio
Townhome
Villa
Yacht
Barn

Location Type

Even More Filters

Features

Managed By

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

Caribbean Vacation Rentals with Air Conditioning(16,702)

16,702 Results
Book it Now!
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
    (71)
    Book it Now!
    • 5 BR,
    • 5 BA,
    • Sleeps 12
      (15)
      Book it Now!
      3 night minimum stay
      • 2 BR,
      • 2 BA,
      • Sleeps 6
        (54)
        Book it Now!
        4 - 6 night minimum stay
        • 5 BR,
        • 5 BA,
        • Sleeps 12
          (132)
          Book it Now!
          3 night minimum stay
          • 2 BR,
          • 1 BA,
          • Sleeps 6
            (46)
            Book it Now!
            3 night minimum stay
            • 3 BR,
            • 3 BA,
            • Sleeps 9
              (40)
              Book it Now!
              2 - 7 night minimum stay
              • 1 BR,
              • 1 BA,
              • Sleeps 2
                (30)
                Book it Now!
                • 3 BR,
                • 3 BA,
                • 1 HF BA,
                • Sleeps 8
                  (19)
                  Book it Now!
                  3 night minimum stay
                  • 2 BR,
                  • 2 BA,
                  • 1 HF BA,
                  • Sleeps 6
                    (30)
                    $215 - $295
                    per night
                    Book it Now!
                    5 night minimum stay
                    • 2 BR,
                    • 2 BA,
                    • Sleeps 6
                      (24)
                      Book it Now!
                      3 - 7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • Sleeps 8
                        (44)
                        Book it Now!
                        7 night minimum stay
                        • 5 BR,
                        • 5 BA,
                        • Sleeps 12
                          (24)
                          Book it Now!
                          2 - 5 night minimum stay
                          • 2 BR,
                          • 2 BA,
                          • 1 HF BA,
                          • Sleeps 6
                            (36)
                            Book it Now!
                            3 - 7 night minimum stay
                            • 5 BR,
                            • 5 BA,
                            • Sleeps 10
                              (48)
                              Book it Now!
                              3 night minimum stay
                              • 1 BR,
                              • 1 BA,
                              • Sleeps 6
                                (24)
                                Book it Now!
                                5 - 7 night minimum stay
                                • 4 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 8
                                  (31)
                                  Book it Now!
                                  3 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 6
                                    (53)
                                    Book it Now!
                                    5 - 7 night minimum stay
                                    • 2 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                      (46)
                                      Book it Now!
                                      7 night minimum stay
                                      • 2 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                        (20)
                                        Book it Now!
                                        3 night minimum stay
                                        • 4 BR,
                                        • 3 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                          (16)
                                          Book it Now!
                                          1 - 3 night minimum stay
                                          • 3 BR,
                                          • 3 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                            (32)
                                            Book it Now!
                                            1 - 2 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 10
                                              (47)
                                              Book it Now!
                                              5 night minimum stay
                                              • 1 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                                (39)
                                                Book it Now!
                                                5 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                  (23)
                                                  Book it Now!
                                                  5 - 7 night minimum stay
                                                  • 5 BR,
                                                  • 5 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 12
                                                    (34)
                                                    Book it Now!
                                                    3 - 7 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 2
                                                      (15)
                                                      Book it Now!
                                                      2 night minimum stay
                                                      • 5 BR,
                                                      • 3 BA,
                                                      • Sleeps 12
                                                        (16)
                                                        Book it Now!
                                                        4 night minimum stay
                                                        • 2 BR,
                                                        • 2 BA,
                                                        • Sleeps 4
                                                          (27)
                                                          Book it Now!
                                                          3 - 7 night minimum stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 6
                                                            (16)
                                                            Book it Now!
                                                            3 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 4
                                                              (54)
                                                               

                                                              Recent Caribbean Reviews

                                                              2014 Family Celebration!!!

                                                              5 of 5
                                                              The property owner Carlos is a gracious and patient man. Our Quest for the perfect vacation started in 10/2013, we decided on San Juan but after speaking with multiple hotels, and private estates, no one came close to the customer service that Carlos gave us!!! He called us instead on bombarding us with emails, his philosophy is that people are starting to lose the ability to verbally communicate, I totally agree! We booked our family vacation on 1/2014, arrived at San Juan 8/13/2014 Carlos had the Shuttle at the airport waiting on all 12 people arriving on 4 different airlines. When we arrived Caracol Che he had a complimentary waiting WOW! The staff was courteous and polite. Now for the Estate!! Every inch of this place was exactly as you see it on the website!!! Please believe me!!! The bedrooms, pool with the lagoon, decks (yes that's with an S), and pool side bar area EXQUISITE!!! My family and I have voted Carlos into the family. WE LOVE YOU CARLOS!!!
                                                              • Submitted: Aug 19, 2014
                                                              • Stayed: Aug 2014

                                                              Amazing Will return to this Penthouse

                                                              5 of 5
                                                              I wanted to thank you so much for allowing my family and I to stay at your amazing and beautiful penthouse. It exceeded our expectations. Walking into that condo/penthouse wowed us all. From the entrance to the terrace on the second floor. The decor (furniture, art work, every decoration), your attention to detail just blew us away. We had so much fun in Aruba but the best part was spending time in the penthouse the views, sunsets, shooting stars at night. All of this is priceless! There was nothing left undone you had it all prepared for us. Thank you again. You take pride in caring for your guest and it shows. What a better place to vacation than your penthouse. You put a lot of thought and work into this penthouse and it shows. We will be back when we return to vacation in Aruba. We will stay no where else you spoiled us too much! We were all sad to leave we felt at home. Again our family vacation in Aruba was nothing short than amazing and spectacular all Thanks to you and your husband again many thanks!
                                                              • Submitted: Aug 18, 2014
                                                              • Stayed: Aug 2014

                                                              Even Better the Second Time!!

                                                              5 of 5
                                                              Returning for our second year to Eleuthera and Whatavue we spend 9 days in paradise. The house was perfect - just like we remembered it from the previous year. It truly feels like your returning home when you open the door. The house is immaculately maintained and stocked with everything we needed for a very enjoyable holiday. Windemere is truly one of the most beautiful, uncrowded beaches on earth. Pat & Gerry are very quick to respond to inquiries and answer any questions about the island or the house. We are already in the process of booking our third visit back to Whatavue. :-)
                                                              • Submitted: Aug 17, 2014
                                                              • Stayed: Jul 2014