The Sandcastle at Calypso
Some beach vacations feel like you're staying in a condo.
The Sandcastle feels like you're moving into your own beachfront home for the week.
Located directly on the beach at Calypso Resort, The Sandcastle was thoughtfully designed for couples, families, and friends who want a vacation that's comfortable, convenient, and wonderfully easy from the moment they arrive.
No crossing busy streets.
No packing up the car to get to the beach.
No sacrificing space for location.
Just unpack, stop by the grocery store, and let your vacation begin.
Why We Love the Second Floor
Many people assume the higher the floor, the better the vacation.
After spending time here, many guests discover something different.
Everything is simply... easier.
Need one more item from the grocery store?
An easy trip.
Heading to dinner at Pier Park?
You're back before you know it.
Want to squeeze in a workout?
The beachfront fitness center is just one floor above, with floor-to-ceiling windows overlooking the Gulf.
Rather take the stairs than wait for an elevator?
They're right beside the condo.
When you're carrying beach chairs, groceries, sleepy children, or just ready to relax after a long day, those little conveniences become some of the things guests appreciate most.
A Balcony You'll Actually Use
Not every beachfront balcony feels the same.
Ours is one of the longer balconies at Calypso, giving everyone room to spread out instead of feeling crowded.
The mature palm trees below create something that's surprisingly rare—a feeling of privacy without taking away the view.
Enjoy your morning coffee in the rocker.
Read a book in the afternoon shade.
Watch afternoon thunderstorms roll across the Gulf.
End the evening with a sunset that never seems to look quite the same twice.
This isn't just another balcony.
For many guests, it becomes their favorite room.
Designed to Feel Like Home
One thing we hear over and over is...
"It looks exactly like the pictures."
That's intentional.
We'd rather pleasantly surprise you with how spacious it feels than disappoint you with clever photography.
The open living area invites everyone to gather together while still giving each person room to relax.
The two recliners were chosen because vacation should actually be comfortable.
The artwork was selected to make the condo feel warm rather than temporary.
The crown molding adds a quiet touch of craftsmanship throughout the home.
Even the televisions work the same way with Roku, so you're not learning a different remote in every room.
Little things?
Maybe.
But those little things add up to a much better vacation.
The Timeout Collections Difference
We believe the best vacations aren't created by having the most amenities.
They're created by removing the little frustrations that keep you from relaxing.
When everything is easy...
When everyone has space...
When you can walk to dinner, step onto the beach, or simply sit on the balcony listening to the waves...
Something changes.
You stop thinking about the schedule.
You stop thinking about work.
You stop thinking about everything waiting for you back home.
And that's what a Timeout is all about.
Check-in time: 15:00
Check-out time: 09:00
Credit Card Processing Fee: 3.00%
Swimming
Bird Watching
Nearby Activities:
Beach
Deep Sea Fishing
Golf
Jet Skiing
Shopping Area
Water Park
Winery
No Booking or Service Fees
Save up to 25% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Aug 01 - Aug 02 2026 | $289 | 3 nights | |||
Aug 02 - Aug 11 2026 | $289 | $249 | 3 nights | ||
Aug 12 - Sep 04 2026 | $249 | 3 nights | |||
Sep 05 - Sep 25 2026 | $270 | 3 nights | |||
Sep 26 - Oct 10 2026 | $286 | 3 nights |
Fees:
Last updated on July 28, 2026

Curtis S.Great unit, great owner service
When we arrived in PCB for our February rental, the resort was doing work in front of the Sandcastle unit, so Penny put us up in another unit of hers, the Shoreline. It was a great unit, but we were able to get into the Sandcastle in a few days. It is a great unit as well, large kitchen and living area. The kitchen was the best equipped of any we've ever stayed at over the past several years. The furnishings were very nice - we have hardly ever had a unit with recliners, and that's a great feature for us. The deck is large and has good furniture. There were a couple of issues that needed attention, but Penny was on it and took care of everything quickly. The basement parking is a major plus! We highly recommend renting one of Penny's Calypso units!
Stayed: January 2026 Submitted: March 03, 2026
Stacey H.The condo is topnotch.
My husband and I enjoyed our stay in The Sandcastle at the Calypso. The unit is beautifully decorated, and I thought I would not enjoy being on a lower floor however, that was not the case. My only regret is that we did not stay longer.
Stayed: April 2025 Submitted: May 21, 2025
Great winter vacation!
We stayed at Penny's condo January and February 2023. This was a spacious and beautiful modern condo with an amazing view from the balcony especially at sunset. The kitchen was also well equipped. We loved that it was within walking distance to Pier Park, shopping and restaurants. Would definitely stay there again.
Stayed: January 2023 Submitted: March 06, 2023
Tiffini H.My new favorite place!
Can't say enough good things about this unit! We've stayed at Calypso many times over the past 10 years and this by far is the BEST. Penny is a great communicator and always there to help. Everything you need is in the unit and location is SUPERB! Go here ASAP!
Stayed: April 2022 Submitted: April 07, 2022
Member since 2021