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8.1

1,917 reviews

Calypso Cay Vacation Villas

Calypso Cay Vacation Villas

4951 Calypso Cay Way, Kissimmee, 34746, Florida, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Free parking

Business center

Free wifi

Free shuttle

Waterslide

Air conditioning

Bar

Sun deck

Calypso Cay Vacation Villas

Welcome to Calypso Cay Vacation Villas, your sunny escape in the heart of Kissimmee, Florida! Nestled just 4.7mi from the vibrant city center, this delightful 3-star resort is the perfect gateway for your adventures in the Sunshine State. With prices starting from just $107 a night, you'll find the ideal home away from home at 4951 Calypso Cay Way, where both relaxation and excitement await!

At Calypso Cay, fun is just around the corner! Dive into our outdoor swimming pool with a thrilling waterslide or enjoy a sunny day on the sun deck with free beach chairs and loungers. Kids will love the playground and the mini-golf, while adults can unwind at our bar or stay fit in the fitness center. Plus, with complimentary Wi-Fi and free shuttle services, you'll have all the conveniences you need to explore the magical world of nearby theme parks. With 1,917 glowing reviews from happy guests, you’ll be joining a satisfied crowd ready to embrace that vacation joy!

Whether you're relaxing in your spacious, air-conditioned villa with a private entrance or enjoying a family picnic in the garden, Calypso Cay Vacation Villas makes every moment count. With amenities that cater to everyone, from free parking to fully-equipped kitchens, your stay will be as comfortable as it is entertaining. So pack your bags and get ready for an unforgettable getaway at Calypso Cay!

At Calypso Cay Vacation Villas, each villa is designed for comfort and convenience, ensuring your stay is as enjoyable as possible. Whether you're settling into a spacious 3-bedroom villa that accommodates up to 20 guests or a cozy 1-bedroom space perfect for couples, you’ll find everything you need right at your fingertips. Each unit boasts a fully-equipped kitchen, allowing you to whip up a delicious breakfast before setting off to the attractions or enjoy a home-cooked meal after a fun-filled day. With air-conditioning and a personal entrance, you'll feel right at home while basking in the Florida sunshine!

Entertainment is at your doorstep, with a wide selection of recreational activities to fill your days. Splash down the waterslide in our outdoor pool, lounge on the sun deck with your favorite summer read, or engage in a friendly competition at the mini-golf course. For those seeking a little more relaxation, head to the on-site bar for a refreshing cocktail, or gather your family for a fun picnic in the lush garden. The possibilities are endless at Calypso Cay, where laughter and family bonding are part of the package!

When it's time to venture beyond the vibrant grounds of Calypso Cay, you'll find yourself just a short drive away from the world-famous theme parks that make Florida a magical destination. From thrilling rides to enchanting characters, the excitement is only a stone's throw away! Plus, with hassle-free shuttle services, you can leave the driving to us and arrive at your summertime adventures ready to create memories that will last a lifetime. Adventure awaits, so book your stay and join the fun at Calypso Cay Vacation Villas!

Closest airports

Orlando International Airport

12.6mi

Orlando Sanford International Airport

33.6mi

Melbourne International Airport

53.6mi

Most popular amenities

Free parking

Business center

Free wifi

Free shuttle

Waterslide

Air conditioning

Bar

Sun deck

Private entrance

Parking On Site

Mini golf

24-hour front desk

Kitchen

Non-smoking rooms

Wheelchair accessible

Beach chairs/Loungers

Elevator

Playground

Picnic area

Garden

Free toiletries

Bathtub

Rooms

Three-Bedroom Villa in Calypso Cay Vacation Villas

Show 12 photos

Villa, Multiple Beds, 3 Bedroom

1 King Size Bed

1 Sofa Bed

1 Queen Size Bed

2 Double Beds

1260 sqft

Kitchen

Private Bathroom

Bathtub

Private entrance

x8

More details

Welcome to our charming Three-Bedroom Villa, a spacious 1259 sqft retreat for up to 8 adults. Enjoy the comforts of a fully-equipped kitchen, a private bathroom with a relaxing bathtub, and unwind in the cozy living area with a flat-screen TV. You'll also find convenient amenities like a washing machine, air conditioning, and free toiletries.

Two-Bedroom Villa in Calypso Cay Vacation Villas

Show 13 photos

Villa, 2 Bedroom

1 Sofa Bed

1 King Size Bed

2 Double Beds

1110 sqft

Kitchen

Private Bathroom

Bathtub

Private entrance

x20

+

x13

More details

Indulge in luxury and comfort in our Two-Bedroom Villa, boasting spaciousness of 1109 sqft and accommodating up to 6 adults and 1 child. Enjoy the convenience of a fully equipped kitchen, private entrance, and enticing amenities such as a bathtub, flat-screen TV, and air conditioning.

One-Bedroom Villa in Calypso Cay Vacation Villas

Show 12 photos

Villa, 1 Bedroom

1 King Size Bed

1 Sofa Bed

720 sqft

Kitchen

Private Bathroom

Bathtub

Private entrance

x20

+

x13

More details

Step into a spacious 721 sqft One-Bedroom Villa that comfortably accommodates up to 4 adults and 1 child. With a fully-equipped kitchen, private bathroom with a bathtub, and luxurious amenities like a flat-screen TV and air conditioning, this villa offers an ideal retreat for a relaxing stay.

Three-Bedroom Villa in Calypso Cay Vacation Villas

Show 12 photos

Villa, 3 Bedroom

1 King Size Bed

1 Sofa Bed

1 Queen Size Bed

2 Double Beds

1260 sqft

Kitchen

Private Bathroom

Bathtub

Private entrance

x20

+

x13

More details

Show 2 photos

Suite

More details

Room - 2 Queen

2 Queen Size Beds

x4

+

x3

More details

King Room

1 King Size Bed

x4

+

x3

More details

Villa, King Size

1 King Size Bed

x20

+

x13

More details

Villa, 2 Double Beds

2 Double Beds

x20

+

x13

More details

Room Selected at Check in

More details

Deluxe

x4

+

x3

More details

Guest reviews

8.1

1,917 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Featured reviews:

🇺🇸

Rebekah

8.2

June 2023

The pool areas were great, lots of fun for the kids, maybe need a little update on cleaning/disinfecting and a coat of paint. Definitely so much better than the last hotel we stayed at in Orlando, we needed a cleaner happier hotel for the rest of the week, and Caylipso Cay was for sure the right choice. I think it would have been nice to have the little coffee shop open a little longer during the day, but not a deal breaker for us by any means. It would also be nice to have the pool open a little longer at night, when we would get home after a long day, our girls couldn't go swimming and the pool didn't open till later in the morning, which also didnt help us bc we had to leave early. The size of the room was amazing, we didn't feel cramped, the kitchen was awesome, a perfect bonus and so easy to take care of our girls from a food stand point. Furniture was great too, we read reviews that Calypso Cay was dirty and extremely dated, however we found it really lovely! Beds were great, bathrooms were too, the washer and dryer were the cherry on top of the cake, so incredibly helpful!

There were lots of other guests smoking weed, that was very frustrating, but we also understand it's not the hotels fault. It would be nice to have a coffee shop/bar/place to get food or snacks over around the pool behind the check in area.

🇺🇸

Brenda

8.2

June 2022

the grounds were very attractive, location, size of accommodations. Everyone that I asked directions or some type of help question was awesome, very pleasant and most helpful

1. I didn’t see any security. 2. After I told the person that gave us the parking pass NO about the tour because of the reason we were in Orlando they called concerning it again the next day. 3. I know this wasn’t the property’s fault but loud music cussing and fighting Saturday night. Scary!!! the next time we stay with you prayerfully circumstances will be different and we can enjoy ALl the amenities you have

🇺🇸

Merideth

10

July 2023

I booked this condo for the price and location. Then I read some bad reviews that the rooms were dirty and there were bugs. This was 100% false. Our condo was perfectly clean and not a bug in sight. The bed was the most comfortable bed ive slept in out of any hotel. The property grounds were so nice. Many pools to choose from, free mini golf and a Starbucks on the grounds. I can't believe how nice it was and how inexpensive it was. We will be staying here every year when we visit.

Some.of the outdoor grills didn't work but there are so many grills that we just moved to another one.

🇺🇸

Michael

8.2

April 2023

Once we changed rooms everything was fine. Pools were very nice, lots of chairs, good pool bar, clean restrooms and lots of kids activities. Pool bar had really good food and food prices were decent.

After checking in our room, the toilet didn't work, maintenance man was in the room till 2 AM (yes 2 AM) trying to fix it. Finally I said enough till tomorrow, spend the entire next day of waiting on and off for diff maint techs to fix it. Wasn't pleased, and requested another room. 2nd room was perfect, they should have done that from the start!!! Pool bar drinks were WAY too expensive, if they lowered the price I'm sure they'd have more business.

🇺🇸

Darren

10

June 2023

I will be honest. I read the comments and saw the pictures after we booked and was sooo horrified that our vacation would be a bust. We got to the resort, had a handicap accessible room and it was sooo nice! It was so clean, the bedrooms were comfortable for the 4 of us and it was one of the best vacations we've had. The kids loved the pool and water slide! The management was nice and all was well. We were in the 5002 building. Thank you Calypso and we will be back!

One slight issue but not a deal breaker. It rains everyday in the afternoon period and the elevator went out. It was ok however and they sent someone to work on it

🇺🇸

Marguerita

9.1

February 2022

everything went well and this was my second time staying here.

I didn't like the fact that the guest service person was never at his station and the front desk had to answer all my questions and I didn't like the fact that the guest service person finally did show up and kept pushing a time share presentation on me when and all I wanted to do is to have a nice time celebrating my husband birthday but the guy was a little pushy and offered us a 100 gift card to to attend this presentation so I respectively declined his offer.

🇨🇦

Richard

8.2

March 2023

Overall the property was roomy, comfortable, and accessible with elevator access.

Pictures are misleading in that all units presented on site show a balcony but our unit had no balcony and we were put off to conclude our stay without rectification even though balcony units were available. Our unit was imediately above a garage that is used by cleaning staff. So, like clock work awakened every morning around 6am by noisy garage door openings and closings.

🇺🇸

Bridgette

8.2

September 2023

Love the location, and the children love the pool area. The staff was very friendly but didn't give much detail about where to go get the parking ticket for vehicle

Our kitchen sink flooded on the 2nd night, so we had to go get the maintenance guy would of had call guest service, but our phone in the room didn't work the kids playing soccer by the pool area is very danger we and other guest had to move cause of them kicking the ball while we trying to enjoy our ice cream by the Starbuck area

🇺🇸

Rodriguez

8.2

June 2023

I enjoyed the proximity of the pool to our bedroom, also enjoyed waking up to its view. The room Jacuzzi was a very good addition, and the living room was spacious for a family gathering. I enjoy that there was a washer and dryer plus all the amenities and utilities included. Location was great! My daughter had a great time

The entrance to the hotel is sort of a maze, so please don’t be confused . I didn’t enjoy that the rooms coffee pot was not working, pull out couch’s bedsheets we’re missing and getting ahold of the front desk was impossible.

🇺🇸

Tabitha

9.1

July 2023

The facilities were very clean and they provided everything we needed. I bought a small thing of laundry detergent because I read the reviews before hand saying they provided everything but I didn’t see laundry detergent. But they provided 2 samples of laundry which was enough for my family for the week. My family enjoyed themselves so much this trip and we’re excited to come back and do it all over again next year!

The only thing I didn’t like was how much they tried to push the time share on us.

Points of Interest Around Calypso Cay Vacation Villas

Attractions

Fun Spot America Theme Parks

1.9mi

Disney Springs®

3.1mi

International Drive

6.5mi

WonderWorks Orlando

6.7mi

SEA LIFE® Orlando

7.3mi

Icon Orlando 360

7.4mi

Madame Tussauds Orlando

7.4mi

Titanic: The Artifact Exhibition

8.2mi

Universal CityWalk

9.5mi

Orlando International Premium Outlets

9.7mi

Amway Center

15.2mi

Lake Eola Park

15.8mi

Winter Park

19.5mi

Wild Florida Airboats and Gator Park

20.7mi

LEGOLAND® Florida Resort

27.2mi

Pools

Location

  • Outdoor

Amenities of Calypso Cay Vacation Villas

Free parking

Business center

Free wifi

Free shuttle

Waterslide

Air conditioning

Bar

Sun deck

Private entrance

Parking On Site

Mini golf

24-hour front desk

Kitchen

Non-smoking rooms

Wheelchair accessible

Beach chairs/Loungers

Elevator

Playground

Picnic area

Garden

Free toiletries

Bathtub

Stay rules - Calypso Cay Vacation Villas

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Curfew

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property

Frequently Asked Questions - Calypso Cay Vacation Villas

What's the check-in and check-out schedule at Calypso Cay Vacation Villas?

The timetable for guests at Calypso Cay Vacation Villas is to check in post 04:00 PM and check out prior to 10:00 AM.

Is there parking available at Calypso Cay Vacation Villas?

Yes, there is parking available at Calypso Cay Vacation Villas. The parking is free and located on site. Additionally, it is public parking and does not require a reservation.

What are the rates at Calypso Cay Vacation Villas?

Calypso Cay Vacation Villas offers accommodations starting at $107. Keep in mind, room types and dates might affect the final price. For specific rates, input your stay dates.

Which room categories can I book at Calypso Cay Vacation Villas?

Calypso Cay Vacation Villas offers three types of villas: Three-Bedroom Villa, Two-Bedroom Villa, and One-Bedroom Villa. All villas are non-smoking and have different room sizes. The Three-Bedroom Villa has the largest size of 1259 sqft and can accommodate 8 adults. The Two-Bedroom Villa is slightly smaller at 1109 sqft and can accommodate 6 adults. The One-Bedroom Villa is the smallest at 721 sqft and can accommodate 4 adults. Each villa has varying bed sizes including King, Queen, Double, and Sofa beds.

What is there to do in Calypso Cay Vacation Villas?

Guests at Calypso Cay Vacation Villas can spend their time at the hotel enjoying a variety of leisure amenities. They can start by taking a refreshing dip in the outdoor swimming pool. The pool offers a fun water slide for those looking for a thrill, and a hot tub/jacuzzi for those seeking relaxation. Guests can then relax on the beach chairs/loungers and soak up the sun. For those who want to engage in some friendly competition, there is a mini golf course available.

Afterwards, guests can head to the bar and enjoy a refreshing drink. For those who want to maintain their fitness routine, there is a fitness center equipped with state-of-the-art equipment. Business travelers can utilize the business center for any work needs. There is also a sun deck available for those who want to unwind and enjoy the beautiful weather. Finally, guests can make use of the playground and BBQ facilities, ensuring there is something for everyone to enjoy during their stay.

Does Calypso Cay Vacation Villas have a pool for guests?

The hotel has an outdoor pool.

What methods of payment does Calypso Cay Vacation Villas accept?

Calypso Cay Vacation Villas accepts payment through credit cards such as Discover, American Express, Visa, and Mastercard. However, cash payments are not accepted.