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  Calypso Cay Resort, Orlando, FL

3 Nights at Calypso Cay
Resort for only $99!

  • Stay 3 Nights In Deluxe Accommodations
  • Enjoy 3 Heated Pool & 18 Hole Miniature Golf
  • Includes 2 Tickets to Castaway Cove Adventure Park
    (Over $60 Value)
  • Free Shuttle To Area Theme Parks

Regular Rate $420.00

Today only $99.00

This Today-Only Deal
Ends at Midnight.

Price Is Per Room For Entire Stay – Not Per Person, Not Per Night

Hotel Overview

Located 7 miles away from Walt Disney World Resort, Universal Studios Florida and SeaWorld Orlando, Calypso Cay Vacation Villas’ luxury accommodations and high quality service will make you feel like you are right at home! Calypso Cay is located amidst the very best of Central Florida’s attractions, as well as having our own array of guest-only activities. You’ll never have to go very far to enjoy yourself!

Calypso Cays pool is surrounded by spacious decks and hosts two full service Pool Bars. Additionally, Calypso Cay boasts their own 18-hole Caribbean-themed miniature golf course. Lush tropical landscaping surrounds the course, offering plenty of shade and brightly colored tropical plants for you to enjoy while trying to make par.

After playing all day, guests can relax and join in on the festivities around the Pool Bar, which offers a full range of refreshments and snacks to enjoy while listening to nightly entertainment at the poolside bandstand. Calypso Cay is designed to be your personal tropical island getaway, far from the hustle and bustle of the real world – yet we’re minutes away from some of Florida’s world-class attractions.

“The Manager Nelson really went above and beyond. To make sure our family had a great stay and he made sure we were happy and comfortable. He really took care of our concerns after talking to him he took care of it right away. Thank You Nelson.”

Beatriz C wrote a review Oct 2019

Room Description

​The Holiday Inn Express and Suites Kissimmee features all-new chic and modernly designed deluxe guestrooms. Each spacious room features two queen beds, complete with refrigerator, microwave, Keurig coffee maker, 42” LED TV, iron & ironing board, and free wireless Internet. Accommodates: 4

Amenities Available

  • Microwave
  • Refrigerator or Mini-Fridge
  • Mini Golf Course
  • Restaurant
  • Multiple Swimming Pools
  • Sun Deck
  • Non-Smoking Rooms
  • Two Heated Outdoor Pools
  • Outdoor Pool
  • Water Sports
  • Parking
  • Wireless Internet Access
  • Arcade / Game Room
  • Elevator / Lift
  • Basketball Courts
  • Fine Dining
  • Business Services
  • Fitness Center
  • Cable/Satellite
  • Hair Dryer
  • Children’s Play Area
  • Ice Machine
  • Children’s Program
  • Jacuzzi/Hot Tub
  • Complimentary Breakfast

“This is a wonderful place for families and couples alike. We stayed in a condo suite and it was wonderful! It was spacious, had a nice screened in deck, huge bathroom and nice kitchen. The resort had plenty to do and had a bar on site as well. We would definitely stay again!”


Why stay here?

  • Complimentary Transportation To Disney World, Seaworld, and Universal Studios

  • 3 Large Resort Swimming Pools With Waterslide, 18-Hole Caribbean-Themed Miniature Golf Course & Tiki Bar

  • Upgrades available to Spacious Villas With Fully Equipped Kitchens

Customer Reviews

Based on 306 reviews

“It’s simply great! Very informative and useful indeed.”

Louis Wong

“This is our third package from 2freenites. Best way to travel hands down.”

Michael Roberts

“I spoke with Kayla on the phone, she was very patient and explained everything well. We really enjoyed our trip”

Joseph Pal

“This page is very informative and knowledgeable. Yes recommendation for this page.”

Eric Nowak

“It’s really a wonderful page and very informative on almost every topic which came into our lives on a daily basis for travelling.”

Awilda Miller

This is a wonderful place for families and couples alike. We stayed in a condo suite and it was wonderful! It was spacious, had a nice screened in deck, huge bathroom and nice kitchen. The resort had plenty to do and had a bar on site as well. We would definitely stay again!


30 Day Money Back Guarantee

No fees, no hassle.
We want you to be satisfied. If you are unhappy for any reason with our services, you may cancel this package without penalty within 30 days from the date of purchase. Cancellations must be submitted in writing. Once your reservation has been confirmed, the package becomes non-refundable even within the 30 days cancellation period.

Frequently Asked Questions

How many days’ notice is necessary to book a reservation?
It is always best to book your reservation as early as possible…ideally 30-60 days in advance. It is also recommended that you book even earlier for peak travel weeks (vacations, spring break, and summer).

Can I book a reservation with less than the required amount of days?
Yes. ​There is at least a 14 day minimum required for bookings and please note all reservations are based upon availability.

If I don’t have dates today but want to lock in the rates how long are those packages good for?
Packages without dates are good for 12 months. They can be extended. If you travels dates are more than 12 months out ask you travel consultant and they will be happy to assist.

Are there any dates I may not book?
No. There are no blackout dates; however, all reservations are based on availability. Peak travel weeks fill up quickly, so we encourage you to book as early as possible.

What time is check-in?
In most cases, you can check into the Welcome Center between 9 a.m. and 6 p.m. However, please double check with your Welcome Center to confirm their hours of operation. Your actual accommodations are not usually available for check-in until 4 p.m. Specific information regarding your reservation is in your reservation confirmation letter.

If I need to cancel my reservation, or change my dates, are there any penalty fees?
You may cancel your reservation for all U.S. destinations, one time, at no cost when changes are made at least 14 days in advance. All non-U.S. locations need a minimum of 25 days to avoid penalties. You may incur a fee if additional cancellations or date changes are made.

Can I transfer my package to someone else?
The package is transferable to anyone who meets qualified adult. However the product must be used within the provided use period given at the point of sale.

How many people may travel on the promotional vacation/package?
Please check the terms and conditions of the promotional vacation package you purchased. Most packages come with either a standard or premium room that can accommodate up to 4 people. Room upgrades or additional rooms are available for a nominal fee. Please check with Customer Service at 888-438-3294 for details

Do you offer discounts on attractions?
For many of our more frequently visited destinations, we have discount offers for meals, entertainment and shopping. You may ask ​the welcome center at check-in. They ​have discounts for many of the local attractions.

Who needs to attend the resort sales presentation?
If married, both spouses must attend. If single, every guest in the party must attend.

How long is the sales presentation?
The sales presentation is 90 minutes long at a minimum.

Are we required to purchase anything at the sales presentation?
You are not required to purchase anything. We only require you and your party to attend the resorts sales presentation.

When does the tour take place?
The tour is scheduled at the Welcome Center upon arrival and is normally set up for the day after you check in.

Can I prearrange the resort’s sales presentation or request a time?
The sales presentation reservations may not be pre-scheduled before arrival at the Welcome Center. A specific tour time may be requested; however, the actual time will be based upon availability and confirmed at check-in.

Is transportation included?
You are responsible for all transportation (Ex: air, car, train, etc.).

What should I do if I am arriving late?
Please contact the Welcome Center if you will be arriving late. Contact information for the Welcome Center is located on your reservation confirmation letter.

How do you check in after the Welcome Center is closed?
Please contact the Welcome Center to which you are arriving. Contact information for the Welcome Center is located in your reservation confirmation letter.

Do you provide shuttles to the parks?
Some of our resort partners do provide shuttle service to the area theme parks. Please contact ​Customer Service​ to confirm your resort’s list of amenities and services.
  • Stay 3 Nights In Deluxe Accommodations
  • Enjoy 3 Heated Pool & 18 Hole Miniature Golf
  • Includes 2 Tickets to Castaway Cove Adventure Park
    (Over $60 Value)
  • Free Shuttle To Area Theme Parks