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HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts

Photo gallery for HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts

Welcome to 'HP 23W Calypso Crossing'!
Spacious & Fully Equipped Kitchen
Cozy Living Area with Ample Seating
Lagoon Style Pool - Perfect for Lazy Days!
Direct Beach Access - Just Steps Away!

Reviews

9.6 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 61315 sq ft

Popular amenities

  • Ocean view
  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View in a map
High Pointe Resort, FL
  • Place, Rosemary Beach
    ‪6 min walk‬
  • Place, Alys Beach
    ‪13 min walk‬
  • Place, Powell Lake
    ‪3 min drive‬
  • Airport, Panama City, FL (ECP-Northwest Florida Beaches Intl.)
    ‪29 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Primary Suite

1 King Bed

Queen Guest Bedroom

2 Queen Beds

2 bathrooms

Primary Bathroom

Queen Guest Bathroom

Spaces

Porch or lanai
Kitchen
Office
Balcony
Outdoor play area

About this property

HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts

NOTICE OF CONSTRUCTION

We would like to inform you that property-wide construction will begin on October 14, 2024, with an estimated completion date of June 6, 2025.

Please note the following:

*Expect loud noise from grinding, hammering, and other activities.
*Balconies will be inaccessible at times, and balcony furniture will be moved into units during this work.
*Some units may be temporarily unavailable for rental during specific phases of the project.
*Schedules may change based on weather conditions.


30A Escapes presents... Calypso Crossing 

- Master Bedroom Gulf Views and Soaking Tub
- Newly Renovated Unit
- One Beach Chair Set Up Included (Seasonally)
- Steps from Shopping and Dining 
- Across the Street from Peddlers Pavilion  

The Ideal 30A Gulf Front Vacation Condo! Newly Renovated Gulf Front Condo at High Pointe Resort in Seacrest Beach with amazing views of the emerald green waters of the Gulf. 

High Pointe is a private gated resort, nestled between Alys Beach and Rosemary Beach. Experience the upscale shops, restaurants and events of Rosemary and Alys Beach all within a 5 minute walk. This tropical 15-acre paradise features five 4-story buildings, two of which are gulf front. The remaining three buildings are set around a family-friendly lagoon pool with graceful palms, tropical flowers and 6 cascading waterfalls. As the sun is setting, relax in the warm waters of the pool-side hot tub or enjoy the spectacular gulf front restaurant/bar with sweeping views of the Gulf.

This upscale 2-bed vacation rental with spacious interiors, fully equipped kitchen, private balcony, washer/dryer and soaking tub. With shuffleboard courts, tennis courts, a children's playground area, a seasonal Gulf side bar and grill, and seasonal children activities, this resort truly has something for everyone. On-site amenities are for the exclusive use of property owners and their rental guests.

Stay in the most exclusive area of 30A at an affordable rate. High Pointe is very much a family destination where wonderful beach memories await! High Pointe offers vacationers the best of both worlds!

High Point Resort Overview:
Exclusive Gulf Side Resort in a Gated Community is Seacrest Beach – The One and Only!
Expansive Pool Deck Featuring a Lagoon Pool, Waterfall Feature, Kiddie Pool and Hot Tub
Beach Front Bar and Grill – Crabby Steve’s 
Private Beach Boardwalk
Amenity-rich 15 Acre Tropical Paradise 
One Tennis Court and Four Pickleball Courts
Children's Playground
Shuffleboard Court
BBQ Grills - Charcoal 
Neighboring Communities – Rosemary Beach and Alys Beach
High Pointe HOA will not allow unregistered guest or visitors onsite 

Important Things to Know:
1) Travel Insurance is NOT included in our quotes. It can be purchased during the reservation process or obtained independently.
2) We DO NOT accept wire transfers for payment. (AMEX, Visa and MasterCard ONLY)
3) Bicycle rentals in High Pointe Resort are available for a fee and provided exclusively by La Dolce Vita. 
4) Beach Chair Set Up Included (Seasonally) for 2023 only. Includes two chairs and one umbrella.
5) Please Note:Beach Chair Service is only provided during the following date range... 3/6 - 10/31 
6) This Community Does Not Allow Golf Carts Inside Of High Pointe Resort
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Sea view

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Vrbo shows your booking, but 30A Escapes processes deposit. If the deposit doesn’t charge, we request an updated card. Once received, you’re all set!
For all the information you need to plan your perfect beach getaway, please visit https://www.visitsouthwalton.com/beach-bay-access-locations/
Office hours are 8am - 6pm CST Text lines are not monitored between 6pm - 8am CST For after-hours emergencies call 850-534-6832

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

Frequently asked questions

Does HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts have a pool?

Yes, this property has a pool.

How much does it cost to stay at HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts?

As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts on 29 Jun 2026 start from £769, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts pet-friendly?

No, pets are not allowed at this property.

How much is parking at HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts?

On-site parking is available at the property.

What time is check-in at HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts?

Check-in begins at 4:00 PM.

What time is check-out at HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts?

Checkout is at 10:00 AM.

Where is HP 23W Calypso Crossing @ High Pointe | Lagoon Pool | Tennis & Pickleball Courts located?

Nestled on the beach, this Rosemary Beach condo building is within a 15-minute walk of Rosemary Beach and Alys Beach. Seacrest Beach and Camp Creek Golf Club are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 40 out of 48 reviews
Rating 8 - Good. 5 out of 48 reviews
Rating 6 - Okay. 2 out of 48 reviews
Rating 4 - Poor. 1 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

9.4/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Christie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing view! Excellent location! Right across the street from restaurants, which you definitely want! And the communication and help from host was great! Highly recommend!
Stayed 4 nights in Feb 2026
Response from VrboOwner on 9 Mar 2026
Thank you so much for sharing your experience! We are delighted to hear the views and location were such a highlight—and that being steps from great restaurants made your stay even better. It is wonderful to know our communication and support helped everything feel seamless. We truly appreciate the recommendation and would love to welcome you back to HP 23W Calypso Crossing anytime you are in the area.
Verified

10/10 Excellent

tom s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Phenomenal view from a very bright and comfortable condominium. Everything in the building is beautiful and very well maintained. The pictures don’t really capture the beauty and feeling of the place.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 20 Nov 2025
Thank you for sharing such thoughtful feedback! We are delighted you enjoyed HP 23W Calypso Crossing's bright atmosphere and phenomenal views. It is wonderful to hear that the building’s beauty and upkeep stood out to you, and we love knowing the experience exceeded expectations beyond the photos. We would be honored to host you again whenever your travels bring you back to 30A.
Verified

10/10 Excellent

Freda F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This condo was perfect for our girls trip. Beautiful view from the patio & close access to the beach. Walking distance to beautiful Rosemary Beach shopping & restaurants. Property managers checked in frequently to make sure everything was great. Loved it!
Stayed 4 nights in Sep 2025
Response from VrboOwner on 6 Oct 2025
Thank you so much! We are absolutely delighted to hear that HP 23W Calypso Crossing was a perfect fit for your girl's trip. The beautiful patio views and close beach access really do make it a special spot, and being within walking distance to the shops and restaurants of Rosemary Beach is such a treat. We are also glad our team could check in and ensure everything was going smoothly during your stay. We would love to welcome you back anytime for another unforgettable getaway!
Verified

10/10 Excellent

Catherine C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location- steps from the beach

Everything went smoothly on our trip. The condo was clean and furnished beautifully. We would stay here again anytime!!
Stayed 4 nights in Aug 2025
Response from VrboOwner on 11 Aug 2025
Thank you so much for your kind words! We’re thrilled to hear that everything went smoothly during your trip and that you found HP 23W Calypso Crossing clean and beautifully furnished — that’s exactly the experience we aim to provide. It means a lot to know you’d stay with us again, and we’d be absolutely delighted to welcome you back for another relaxing 30A getaway!
Verified

10/10 Excellent

Brittney F.

Liked: Cleanliness, communication, location, listing accuracy
We were in rosemary beach for a Girls trip. This was a Great location, close to pool and beach, shopping, and restaurants! The management did a great job of communicating and helping with small issues.
Stayed 3 nights in Aug 2025
Response from VrboOwner on 21 Aug 2025
Thank you so much! We're thrilled to hear that your girls' trip to Rosemary Beach was a success and that the location worked perfectly for your group. Being close to the pool, beach, shopping, and restaurants really does make for a fun and convenient getaway. We also appreciate your kind words about our team—it’s always our goal to be responsive and helpful, and we’re so glad we could assist during your stay. We'd love to welcome you back anytime!
Verified

10/10 Excellent

Polly F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location overlooking the gulf. Amazing sunsets, beach chairs and umbrella was provided . On the same property as Crabby Steve’s. Walking distance to Rosemary & Alys beach. Live entertainment nightly across the street at Peddlers Pavillon. Everything you need in one location. Pickleball courts, pool and hottub. The condo was a perfect fit for our family. Great memories made. We will be back!
Views from our balcony
Sunset
Crabby Steves
Stayed 4 nights in Oct 2025
Response from VrboOwner on 23 Oct 2025
We are overjoyed that you and your family found everything you needed at HP 23W Calypso Crossing for a magical beach escape. From breathtaking sunsets and a convenient seasonal beach setup to the vibrant energy of Peddlers Pavilion and the charm of nearby Rosemary and Alys Beach — it sounds like the perfect blend of relaxation and fun. We are so glad the condo felt like a perfect fit, and we can't wait to welcome you back to make even more beautiful memories!
Verified

10/10 Excellent

Rob B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great water view and everything was just as it appeared online.
Stayed 7 nights in May 2025
Response from VrboOwner on 24 Jun 2025
Thank you for your kind words! We’re so glad you enjoyed the Gulf views at HP 23W Calypso Crossing and that everything lived up to your expectations. We'd love to welcome you back for another relaxing stay anytime!
Verified

10/10 Excellent

Sarah W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was great and very quick response time, took care of everything we needed and was exceptional communication. Not to mention how great the view is, and how nice the patio chairs are. Beds and pillows were comfortable. It was also a very clean unit compared to some of the others we have stayed in at High Point in the past. My only recommendation is to do laminate flooring instead of the tile. We had two free beach chairs/ service for the week as well. Highly recommend and we will be back next year!
Stayed 5 nights in Oct 2025
Response from VrboOwner on 3 Nov 2025
Thank you so much for your kind words and thoughtful feedback! We are thrilled to hear you enjoyed your stay at Calypso Crossing and appreciated the view, patio setup, and cleanliness of the unit. It is great to know the beds and pillows were comfortable and that the seasonal beach chair service added to your experience. We appreciate your recommendation and look forward to welcoming you back next year!
Verified

10/10 Excellent

Dana H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun family beach vacation

First time staying in 30A and we will be back. This condo had stunning views. Rosemary Beach shops and restaurants were a short walk from the condo. We will be back!
Stayed 5 nights in Jun 2025
Response from VrboOwner on 17 Jun 2025
Thank you for your kind review! We are thrilled to hear that you had such a wonderful experience during your stay at HP 23W Calypso Crossing. It's great to know that the stunning views and the convenient location near Rosemary Beach made your visit so enjoyable. We look forward to welcoming you back again soon.
Verified

10/10 Excellent

Deana D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Condo on the Gulf

Great place to stay , on the gulf , walking distance/ biking to shopes and restaurants.Very clean , renovations front of condo finishing up . Our view of gulf unobstructed.
Stayed 4 nights in Apr 2025
Response from VrboOwner on 24 Apr 2025
Thank you for the wonderful review! We're delighted to hear that you enjoyed your stay with us at HP 23W Calypso Crossing. It's great to know that the location, cleanliness, and the view of the Gulf were all to your satisfaction. We appreciate your feedback and look forward to welcoming you back in the future.
Verified

10/10 Excellent

Jonathan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great condo

We enjoyed our stay. Property had everything we needed and location was fantastic. Would stay here again.
Stayed 5 nights in Jul 2023
Response from VrboOwner on 14 Jul 2023
Thank you Jonathan for staying with us and for the awesome review! We're so happy to hear you had a good time at High Pointe 30A. Please come back and stay with us again soon!
Verified

10/10 Excellent

Dawn R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Our stay was great! We had a fantastic view, clean rooms, and free bikes with the unit. We loved our stay and will be back!
Stayed 7 nights in Jun 2021
Response from VrboOwner on 16 Jul 2021
Thank you Dawn for staying with us and for taking time to leave a review! We're so happy to hear you had a good time at this Seacrest Beach rental and your feedback is much appreciated. We hope you'll stay with us again in the near future!
Verified

10/10 Excellent

Alexandra C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

It was clean and has the most beautiful views!! Great location. Very close to Rosemary.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 1 Dec 2023
Alexandra - Thank you for staying with us and for taking time to leave such a nice review! We're so happy to hear you had a good time. Please come back and stay with us again in the near future!
Verified

10/10 Excellent

Kayce G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great condo!

Great condo with amazing views and perfect location!
Stayed 5 nights in Apr 2021
Response from VrboOwner on 23 Apr 2021
Thank you Kayce for staying with us and for taking time to leave a review! We're so happy to hear you had a good time at this Seacrest Beach rental and your feedback is much appreciated. We hope you'll stay with us again in the near future!
Verified

10/10 Excellent

Julie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring Break 2024

We had a wonderful time at the beautiful condo. It was so close to the beach, shopping and restaurants that we were able to walk everywhere. We will definitely come back to stay again!!
Stayed 4 nights in Mar 2024
Response from VrboOwner on 3 Apr 2024
Julie - Thank you so much for staying with us and for the awesome review! Your feedback is greatly appreciated and we're so happy to hear you had a good time. Please come back and stay with us again soon!
Verified

10/10 Excellent

Cydney F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved our stay!

wonderful location and unit! Everything was wonderful! Will be back!
Stayed 7 nights in Aug 2020
Response from VrboOwner on 31 Aug 2020
Thank You Cydney for taking time to leave such a nice review! Your feedback is greatly appreciated and we're so happy to hear you had a good time at this 30A High Pointe Resort rental. We hope for the opportunity to host you again in the near future!
Verified

10/10 Excellent

Kristen I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Condo

It was clean and comfortable and we loved the location. Watching the sunsets from the patio every night was amazing. Thanks for letting us stay in your beautiful condo!
Stayed 5 nights in Oct 2023
Response from VrboOwner on 3 Nov 2023
Thank you Kristen for staying with us and for taking time to leave such a nice review! We're so happy to hear you had a good experience. Please come back and stay with us again soon!
Verified

8/10 Good

Patricia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Property was very clean

We had a great time there. Everything was as described and more. Thanks
Stayed 2 nights in May 2024
Response from VrboOwner on 22 May 2024
Patricia - Thank you so much for staying with us and for the awesome review! Your feedback is greatly appreciated and we're so happy to hear you had a good time. Please come back and stay with us again soon!
Verified

10/10 Excellent

Kelley B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect week at 30a

We had a great time at High Pointe Resort 23W. The condo was cute and well stocked. Great location and so nice to have Crabby Steve’s on property to grab a drink and awesome food! We would definitely come again!
Stayed 7 nights in Jul 2021
Response from VrboOwner on 16 Jul 2021
Thank you Kelley for staying with us and for taking time to leave a review! We're so happy to hear you had a good time at this Seacrest Beach rental and your feedback is much appreciated. We hope you'll stay with us again in the near future!
Verified

10/10 Excellent

Elizabeth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and comfy condo

This was our 2nd year staying at this condo and we had another wonderful trip! Thank you for sharing it with us!
Stayed 7 nights in Jun 2023
Response from VrboOwner on 13 Jul 2023
Thank you Elizabeth for staying with us and for the awesome review! We're so happy to hear you had a good time at HP 23W Calypso Crossing. Please come back and stay with us again soon!
Verified

10/10 Excellent

William M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

great location

Updated clean unit in great area. Only thing needed is a corkscrew for wine bottles.
Response from VrboOwner on 4 Apr 2020
William, We are so happy to here you enjoyed your stay! Thank you for the feedback, we have purchased a corkscrew for the unit. We hope you stay with us again in the future.
Verified

10/10 Excellent

Elizabeth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful view!

We loved our stay here! The condo was beautiful and I loved the addition of a sectional couch, plenty of room for all of us. We also loved the waking/biking community so close to the condo! Thank you for sharing it!
Stayed 7 nights in Jun 2022
Response from VrboOwner on 18 Jul 2022
Thank you Elizabeth for staying with us and for taking time to leave a review! We're so happy to hear you had a good time and hope you'll stay with us on 30A again in the near future!
Verified

10/10 Excellent

Amy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect weather for a quick fall trip to 30-A

I love staying at High Pointe! This is my 6th stay at this property. This trip, was with my 2 adult daughters, and we had a great girls weekend. We ate in our favorite restaurants (outdoors), shopped, and enjoyed lying on the beach in the beautiful warm sunshine.
Stayed 3 nights in Oct 2020
Response from VrboOwner on 18 Nov 2020
Thank You Amy for staying with us and for taking time to leave such a nice review! Your positive feedback is greatly appreciated and we're so happy to hear you had a good time at this 30A High Pointe Resort rental. We hope for the opportunity to host you again next time you vacation in South Walton!
Verified

10/10 Excellent

Cheri B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and updated unit with amazing views

Excellent
Stayed 4 nights in Jan 2021
Response from VrboOwner on 26 Feb 2021
Thank You Cheri for staying with us and for taking time to leave such a nice review! Your positive feedback is greatly appreciated and we're so happy to hear you had a good time at this High Pointe Resort rental. We hope for the opportunity to host you again next time you vacation on 30A!
Verified

8/10 Good

Cassie H.

Liked: Check-in, communication, location, listing accuracy

Great location for families

Overall was a nice property and great location. Very convenient (pool, beach, Crabby Steve's, restaurants across street) for our family with young kids. Beds were comfortable! Unit itself needs a deep clean (fans dusted, washer had mold, grout is black, etc). Playground could use some maintenance as well (lots of ants and weeds else we would have used more).
Stayed 7 nights in Sep 2022
Response from VrboOwner on 3 Oct 2022
Thank you Cassie for staying with us and for the review. Your feedback is greatly appreciated and will help us make necessary improvements. We're happy to hear you had a good time and hope you'll stay with us on 30A again soon!

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