We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
“Fantastic”
other travellers have booked this property
Your view from the living area out to the infinity edge pool. Exceptional mornings and sunsets!
Bookings for this home are first-come, first served. Lock in your dates before they are gone
Your view from the living area out to the infinity edge pool. Exceptional mornings and sunsets!
Your living area with open gallery and takes you out to the infinity edge pool. Come & Just EXHALE! Your performance kitchen designed for groups of up to 8 adults. Local chefs love our kitchen!
Check Availability
Request to Book
Make Enquiry
Excellent
93 reviews
Your view from the living area out to the infinity edge pool. Exceptional mornings and sunsets!
Your living area with open gallery and takes you out to the infinity edge pool. Come & Just EXHALE!
Your performance kitchen designed for groups of up to 8 adults. Local chefs love our kitchen!
Another angle of the large and comfortable kitchen...
Wider angle of GOC's performance kitchen & indoor dinning area for your enjoyment...
This is your super master bed chamber! Double headed outdoor shower & 2 verandas one facing sunsets
A differnt angle of your super master bed chamber. 17' high ceilings truly a royal chamber to rest.
Grand Outlook Castle located on a private & secure point of land with views of true forever...
Your arrival at the Grand Outlook Castle (GOC) is simply impressive for all in your entourage.
Your private & secluded castle infinity edge pool. OH! It is bathing costume optional. U CAN EXHALE!
Newly installed cable railing allows for extensive unencumbered views of Paradise
This rare sunset is a 'Blue Sunset'... Taken right from the comfort of your lounger. Cameras please!
Our castle's gardens embrace you. THIS is how beautifully you will be greeted by butterflies.
What can you say... PRICELESS!
This sunset taken 4/27... sent to us by the then guests... the views are amazing! Thanks Artie!!!
Another world class sunset from Grand Outlook Castle. See the rare green flash OFTEN!
Grand Outlook Castle's views are so amazing guests have been known to levitate!
Peaceful & secluded infinity edge pool is... Come & take a NAP...!
Our honeymoon couples proves a good marriage makes both spouses stronger. Wishing many happy years!
Another fantastic sunset from Grand Outlook Castle this one on March 12th w/ $200M in yachts below
Another extraordinary sunset from Grand Outlook Castle
Another amazing sunset from Grand Outlook Castle. This one taken on OCT 19, 2012
Grand Outlook Castle's view featured in AXA magazine 'Absolutely Anguilla' under SPECTACULAR VILLAS
10-18-10 castle sunset! A daily miracle of nature for your enjoyment. Another Green Flash evening!
Grand Outlook Castle's mornings greet you with new neighbors and a motionless mirrored sea. AMAZING!
2ND floor plan. Many great changes since. Super Master Bedroom 50% larger w/ TWO outdoor showers
First floor plan. Also, many great changes since this rendition. See outside shower at lower right
Grand Outlook Castle from DaVida @ Crocus Bay Beach... a TRUE landmark on the island of Anguilla
Our Castle sits majestically over Crocus Bay Beach with spectacular views and access to Crocus Beach
Rainbows visit the castle after brief showers sweeps across Anguilla. FULL rainbows are common.
Shoal Bay East  IS one of the top 10 beaches in the WORLD a short ride from Grand Outlook Castle
World famous Little Bay Beach is within hiking distance. Spectacular CALM snorkeling for all levels.
Anguilla... Best Beaches! Great waves! Perfect water! Just visit and get to finally... EXHALE!
HUGE views, a personal sense of peace & serenity are unrivaled at Grand Outlook Castle. COME EXHALE!
Simply... One of the most stunning views in the WORLD!
Grand Outlook Castle, one of the most romantic settings in the WORLD. We embrace Honeymoons ALSO!
The Castle pool is always comfortable and always entertaining. You\'ll ALWAYS be AMAZED!
Two friends enjoying a glourios morning at Grand Outlook Castle's pool... Truly a grand view
You'll never know who will visit our pool Ducky... a 60 foot Catamaran on this day
Crocus Bay Beach at the castle's infinty edge pool. You CAN NOT fall off! But, you can fall in LOVE!
Here is that sunset!!! No BETTER place to view 100% of EVERY sunset! See sea turtles & pelicans fish
20% of the view from our castle's tower. 200 feet above the sea. 5 times this VIEW for YOU to SEE!
Another amazing sunset at Grand Outlook Castle 10-19-11
Calvin's boat to Little Bay just down the hill from Grand Outlook Castle
Dinning al fresco with amazing views at Grand Outlook Castle
Double headed outdoor shower at Super Master B/R with stunning day and night views & very private!
Shoal Bay East beach at Gwen's a Top 10 World beach. 10 minutes from Grand Outlook Castle
Appoaching the castle on a impressive day. The views from GOC are always dramatic & impressive
'Ducky' pointing to the view and taking the water's temperature,
Another Stunning view from Grand Outlook Castle over the island know as Prickly Pear
Always! A relaxing event at Grand Outlook Castle. NOW, where else would you want to be?
Intimate dinning at sunset. Dine and be entertained at the same time... Very easy!
Another stunning morning image at Grand Outlook Castle... Bring CAMERAS. Constant photo ops.
Another stunning Grand Outlook Castle sunset. Each a true work of art.
Crocus Bay Beach during the Queen's Birthday Celebration and sailboat race.
Junior's glass bottom boat tours... He'll come pick you up down in Crocus Bay Beach
Sunrises at Grand Outlook Castle are very vivid also. Beauty is all around you all the time
YES! We have some banana trees at Grand Outlook Castle AND organic bananas for you.
Another stunning & unique sunset...
Views that truly promote wonderful mutual feelings of awe...
Water skiing at dusk below Grand Outlook Castle. Can arrange for YOU to waterski for your 'fans'
Crocus Bay Beach from Grand Outlook Castle with the highest cliffs on Anguilla just above.
Did we say pink sunsets? Yes we have pink sunsets AND green flashes at Grand Outlook Castle
Gas grille area with 2 burner stove and shade sail... be a 'chef' and NEVER miss the great views
Snorkling & dive trips just a short ride from Grand Outlook Castle
Two in the infinity edge pool at Grand Outlook Castle
Private massages on the north west deck... very private!
Private massages on the south west deck... very private with spectacular views.
Sailboat race from Grand Outlook Castle's living room ... Who needs television when this is reality?
The British are coming... British warship just off Grand Outlook Castle
Did we mention the relaxing views?
Outside dinning at sunset by candle light... where else would you want to be?
Did we mention the unrivalled, spectaular and unique sunsets? With these views U can't be redundant
Pink sunsets? At Grand Outlook Castle
British warship in Sandy Ground for R&R
On of the most romantic locations anywhere AND we offer the entire castle to a single couple often
A ray of sunshine cast onto Crocus Bay appears nearly Bibilical
There IS an art collection at Grand Outlook Castle... SHHHHHH!
Rainbow from GOC pool deck morning of 2-7-12 last week
NOW choose a favorite sunset
This one?
Or This one? The pool lights are on... neat!
This one Maybe? Do you see the 3 masted schooner?
Could the Blues be most appealing?
Maybe the pinks? What color speaks to you?
the sunset from 2-2-12
Sunset from GOC pool deck 2-9-12 this month
The view on the morning of March 12th
The view of a ship powering away from Grand Outlook Castle... AMAZING VIEWS!!!
Grand Outlook Castle is this relaxing. So easy  to just take a nap!
OUR WISH TO YOU FOR A 'HAPPY NEW YEAR'!
This property is not available for these dates.
Don't give up! Enquire about other rentals just like this one that are available -
Show all rentals available
Overview
Castle -
4 Bedrooms, 5 Bathrooms, Sleeps 10
Sandy Ground, Anguilla

Reviews from our community

Excellent - based on 93 reviews
Write a Review

Reviews from our community

Date | Rating
  • English first
  • Any
English first
English first
Any
English first
Terri M
West Chester, PA
Level 2 Contributor
5 reviews
common_n_hotel_reviews_1bd8 4 helpful votes
“Fantastic”
Reviewed 26 December 2017 for a stay in December 2017

We stayed at Grand Outlook Castle December 12 - 18, 2017. There really are not words to describe how beautiful it is. The house is gorgeous, and the view is amazing. It is hard to stop looking at it. Pictures do not do it justice. Paul and Elise did a great job getting the house up and running after the Hurricane.
About eight years ago my husband and I looked up at the house from daVita and joked about staying there for my 60th birthday. Paul and Elise helped him pull off the surprise, along with our kids, even with the uncertainty with Irma. Everything was taken care of to make our transition smooth from St. Maartin to the Castle and back to the airport. We were met at the airport and transferred to the Calypso crew for the boat over to Anguilla. Wendell Connors met us at the Blowing Point Ferry Terminal with our rental van and took us to the Castle - we even stopped at a store to get some initial supplies. We were greeted at the Castle by Catherine who gave us a tour and got us settled. Ms. Rolyn and her staff made sure we had everything we needed. I know I missed someone - but thanks to all. We are so glad we did not cancel.
The staff are so nice and made the stay even more special taking care of all the little details.
The island is slowly recovering, and it is amazing to see their resiliency. They are warm, welcoming and genuine.
Some of the beaches still have debris but Shoal Bay East is gorgeous, and Hank's is open and serving with a smile.
At Sandy Ground, a number of restaurants are open. We went to Elvis', Roys, and Johonnos. daVita opened while we were there with full menu and bar selections.
Rendevous bay still has some needed work but Coconuts was open for drinks and getting ready to start food.
It was a great birthday celebration with family in paradise. Again -thanks to all.

Your age range 50-64
Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
27 Dec 2017
Dear Terri & Dale,

Your most kind and most honest words put tears in both Elise and my eyes. It has not been an easy task for anyone on Anguilla since Irma. HOWEVER, we can still share with guests to Anguilla " a great birthday celebration with family".
We and our staff are thrilled to have accomplished that for you and we TOO are happy you did not cancel. Thank you again for caring, trusting us, your sincere support of Anguilla and honest bravery!

CHEERS!
Elise & Paul
Catherine & Gifford
Ms. Rolyn and her staff
The Grand Outlook Castle

TGYC!
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
4awallace
Sebastian, Florida
1 review
“Absolutely incredible!”
Reviewed 20 November 2017 for a stay in October 2017

We just returned from a two week stay at the Grand Outlook Castle for my wife's 50th Birthday and we absolutely loved the island and the accommodations!!!
Elise & Paul went above and beyond our expectations in getting the GOC ready for us so soon after Irma.
They had a whole house generator installed and must have worked their tails off cleaning up and getting things ready for our arrival.
Obviously there was massive damage on the island from Irma but the people were so friendly and made us feel so welcome it was amazing!
This island is truly something special and we made many new friends, ate incredible food(too much!) and swam and played on the most beautiful beaches I've ever seen, and we have travelled to many many islands!
The GOC is absolutely beautiful and the pool and outside area are perfect for entertaining, we had two couples join us and there is plenty of room for all!
If you are thinking of going to Anguilla they are open for business, groceries, booze, and great restaurants ready to show you a great time, it was a trip of a lifetime and we will definitely return soon!!

Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
22 Nov 2017
Dear Heidi, Andy, Becky, Brad & Martha, You folks are heroes to us on Anguilla. When relief flights were still the main method of air transportation, you came to Anguilla. When there was no electricity on much of the island, you came to Anguilla. When most Americans were afraid of coming to most anywhere in the Caribbean, you came to Anguilla... AND really helped everyone out of a mess as best you folks could. Know I speak for all Anguillians when I write, THANK YOU! Will never forget our first day shopping spree and how you made Anna nearly cry when her credit card machine was not working and THEN! Heidi came up with the cash... Anna said JUST before that miracle, I hope I don't have to put all that back!" What a special MOMENT! KNOW there were many more such memories and that is what has made the effort to have you come in spite of all the trepidations and concern... You gave Anguilla a lot more HOPE when we all had little! TGYC! Elise & Paul, Katie & Gifford, Rolyn & Sue and the entire staff of Grand Outlook Castle and the people of Anguilla.
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Josh S
1 review
“Breathtaking perection”
Reviewed 27 June 2017 for a stay in June 2017

This was our second stay in beautiful Anguilla with Paul and his fantastic team. This time we had the pleasure of staying at the G.O.C. and it certainly did not disappoint. From setting up island transfers, boat rentals or recommendations the team left nothing to be desired. Anguilla and the G.O.C. has defiantly become our home away from home and we cannot wait to return next summer

Your age range 35-49
Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
29 Jun 2017
WOW Josh!

We love your sentiments and are thrilled to have you, your family and friends return to Anguilla and Grand Outlook Castle AGAIN in 2018...

Have a great summer and let's chat in September.

Gratefully,
Elise & Paul AND "the fantastic GOC team"

TGYC!
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Jayne L
Aberdeen, United Kingdom
2 reviews
“Paradise”
Reviewed 17 April 2017 for a stay in March 2017

Beautiful well equipped villa ,spacious and had everything you need to have a perfect holiday.we ate in most of the time as the kitchen was excellent and the barbecue area very pleasant to relax in.the staff were most helpful and ensured everything was good.i especially enjoyed the outdoor showers and swimming pool
Jayne

Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
18 Apr 2017
THANK YOU JANE...

It was just a wonder to have you and the "crew" with us at Grand Outlook Castle.

AND after you 8 folks had been bareboating for a week prior. You kids know how to live!!!!

Elise and I are THRILLED!... You enjoyed both the infinity edge pool and outdoor showers.

We are certain that you and your groom appreciated that the outdoor showers at Grand Outlook Castle which ARE with two separate heads... one for each! HAHAHA!

CHEERS & THANKS!
Elise & Paul with Katie & Gifford, Rolyn, Sue, Junior, Ron, Wendell and all our other staff.

TGYC
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
513travel...
Cincinnati, Ohio
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
“Beautiful setting and view but no 1st floor AC - living area uncomfortable”
Reviewed 10 April 2017 for a stay in March 2017
1
person found this review helpful

Beautiful grounds, bedrooms spacious with beautiful balcony views. Kitchen well equipped but too uncomfortable to cook because NO 1ST FLOOR AIR CONDITIONING for living room, dining area and kitchen. Our group of 8 only cooked in one night because it was so unpleasant. There are fans but they didn't cool it off and only increased the noise level. Instead of gathering together in the evening we found everyone going to their separate bedrooms where it was more comfortable. The advertised concierge service was unrealiable. Would not have booked if we knew there was no AC as mentioned above.

Would you recommend this hotel to a friend?   No.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
18 Apr 2017
THESE COMMENTS ARE APPRECIATED AND THE AUTHOR IS CONTEMPLATING A MORE ROUNDED REVIEW REVISION.

*** Grand Outlook Castle has over 200 all 5 star guests reviews on three separate sites... which do tell MANY different experience.

TGYC
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Mcsimpson...
Level 2 Contributor
6 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
“Fabulous villa! Exceeded our Expectations!”
Reviewed 7 April 2017 for a stay in March 2017

Spent a fantastic week here celebrating my husbands 60th, with 3 other couples from Scotland. From the booking, our arrival and stay, everything was well organised and straightforward. The owners sent us an information pack before we arrived, which was very helpful. GOC exceeded our expectations, providing us with spacious, luxurious accommodation, and amazing views over the ocean from the pool deck and infinity pool. The villa was extremely well equipped - all we needed were our clothes. The staff were helpful, and quick to respond to a minor issue we had. Would highly recommend this villa, and would love to be able to stay again.

Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
9 Apr 2017
Dear Muriel, we would look forward to your return to Grand Outlook Castle AND True Paradise.

PLEASE send our best wishes to "Captain Jack" on his successful mission and 60th Birthday...
CHEERS!
Elise & Paul
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Thomas S
Lincoln, Massachusetts
Level 1 Contributor
3 reviews
“Our best vacation, nicest location, Ever!”
Reviewed 13 February 2017 for a stay in January 2017

I would like to share a few words that describe our 2 week vacation in Paradise. Peaceful, beautiful, amazing, blissful, fun, warm, quaint, casual, comfortable, outstanding sunsets, extremely safe and a ton more. This romantic home is very conveniently located at the top of the hill in highest section of Crocus. The Castel is extremely spacious, very nicely decorated, very well appointed, private and quiet. The beaches are never crowded and amazing, the food outstanding and the locals couldn't have been nicer. We cant wait to visit Anguilla island again and share our experience with the rest of our family.
Thank you Paul and Elise for allowing us to share your paradise!
Tom & Denna

Would you recommend this hotel to a friend?   Yes.
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Management Response
15 Feb 2017
Dear Tom & Denna,

We are so happy that we were able to deliver to you two your "best vacation... Ever!" WOW!
That is exactly what our sincerest mission is!

"To exceed the highest expectations of our honored guests!

We can't wait for your return... which you have already booked; THANK YOU!!!

When we finally find True Paradise, as we all have on Anguilla, the future becomes much easier because you know where you love to go AND what you will receive in return; "Peaceful, beautiful, amazing, blissful, fun, warm, quaint, casual, comfortable, outstanding sunsets, extremely safe and a ton more"... Tom & Denna, we just LOVE your words.

Gratefully,
Elise & Paul with Katie & Gifford, Rolyn, Ron, Junior, Wilson, Wendell et al
Grand Outlook Castle #1 guest rated rental in the Caribbean...

TGYC!
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Enter dates for more accurate prices
2 guests
Adults2
Children0
Apply
Do you own a holiday rental? List it here.
Extra income
Earn money by renting out your home. With no up-front fees and no contract, you keep more for yourself.
Easy to manage
Confirm bookings in one click and track everything from enquiry to check-out – even while you're on the go.
Trusted by travellers
With millions of reviews and protected online payments, TripAdvisor helps travellers book your home with confidence.
Set up your free listing