About the property
- Castle7222 sq. ft.
- Half Baths1
- Minimum Stay5 - 7 nights
"it is ALWAYS Summer on Anguilla!!!"
Dear True Paradise Researcher,
Elise & I are very pleased AND HONORED to have your most kind interest in our version of True Paradise!
* FREE up to $10,000 in Travel Guard travel insurance. Coverage for flight delays or cancellations, emergency evacuation AND if there is almost any reason the castle or Anguilla does not meet your fully justified standards. Please request to book your dates HERE and we will arrange for your "NO WORRIES!" insurance ... HAPPY TO HELP YOU HELP ANGUILLA RECOVER FURTHER FROM IRMA...The rest is very easy! Details will be given upon acceptance of your booking request!
PLUS! Anguilla has always been and remains a very safe and relaxing island...
JUST BACK AFTER TWO GLORIOUS WEEKS ON ANGUILLA!
1.) Flew onto Anguilla from San Juan right on time!
MANY Restaurants are open and the airport and docks are operating so guests can come and go directly from Anguilla. All of Anguilla has electricity.
OH... the golf is open and not crowded.
The large resorts are coming back with ZEMI BEACH opening on FEB 15th and the FOUR SEASONS ON MARCH 1ST. They are opening because Anguilla is back but needs you back with... "NO WORRIES!"
ANDY of Vero Beach Florida wrote!; ...
"We arrived on Saturday October 21st at The Grand Outlook Castle for a two week stay for my wife's 50th Birthday.
We are fortunate to have a castle with a full house generator, power is scarce* but we had no trouble arriving through San Juan airport then flew into Anguilla. ( *Grand Outlook Castle and most of Anguilla has had full power for three weeks now) HURRAY!
Andy's car rental was great and we have had a blast, the people are fantastic and the food at Roy's and Tasty's and Ocean Echo, and Madeiraman has been great! I'm so happy to be here helping these great people heal from this awful storm, the beaches are so beautiful, the water incredible, if you are thinking of coming to Anguilla please do so, it is beautiful and they need to have our support!"
As Andy so well and kindly notated, the island is easy to get to, it is safe and the folks here love you!
The island is calm and the beaches are still as beautiful as before IRMA.
There may be a somewhat limited choice for outside dinning BUT both Blanchards' restaurants, many island restaurants will be open and Zemi resort may open for FEB 1 if the demand ramps up. U can follow us on Facebook Grand Outlook Castle-Anguilla
IF you have thought about visiting Anguilla in the past, this may be a most special and unique time with the island recovering quickly..
Grand Outlook Castle STILL IS the #1 Rental Option in the entire Caribbean with 132 ALL 5-STAR ACTUAL guest reviews. Our testimonials are penned by ACTUAL folks who have paid for and enjoyed the full Anguilla/Grand Outlook Castle experience . ALL agree "WE will return!"
Our ACTUAL prior guests' words tell the story you need to know to make the best decision for your retreat to True Paradise and your worthy efforts you have made to have found The Grand Outlook Castle.
Grand Outlook Castle IS located on a truly amazing site and our infinity edge pool faces each amazing sunset as does each separate bed chambers. ALL 4 bedroom suites are Master Bedrooms with private verandas and private 2 person hammocks... No drawing straws for that tricky 4th "bedroom" that was really a closet and no one wants
Grand Outlook Castle WILL exceed you and your party's expectations. No image or description can ever replicate the experience of entering the castle's gated & flowered compound of bold oleander & bougainvillea with hummingbirds and distracting turquoise sea views. You will be drawn into the stunning castle designed specifically to expose you gradually to ever expanding sea views.
With each step, you move closer to a massive view of 'Mother Nature's' finest works. Guests are thoroughly captivated by the experience... your expectations will have already been exceeded!
Grand Outlook Castle IS EASY! Our rates include ALL fees & tax
Grand Outlook Castle is a truly amazing structure, on an amazing site and one of the best if not the best islands in all the Caribbean.
As we say most sincerely, 'Come… & Just Exhale! ” tm
Please read a few of our 79 oops 97 oops 100-ALL 5 STAR guest reviews; you too will absolutely agree! AND... 100% of ALL prior Grand Outlook Castle's guests happily confirm 'they WANT to return'. You will also!
Grand Outlook Castle is an AWARD WINNING, modern and stunning oceanfront estate. Grand Outlook Castle is a truly compelling venue for 2 to10 guests. Whether a family-friend reunion, anniversary-birthday celebration OR an intimate honeymoon for just 2, Grand Outlook Castle accomodates you ALL in grand fashion.
Our rates include all taxes/fees, are adjusted to accommodate your vision of spectacular Anguilla and the total number of guests within a very reasonable budget for true Paradise. Our castle's 1-4 bed chambers are ALL spacious MASTERS w/ BIG ensuite baths, A/C, very private balconies and amazing views.
Two bed chambers have stunning double headed outdoor showers and ALL are most accommodating to even the most discriminating of guests. Everyone in your group receives a most wonderful private space with complete privacy and stunning views from every window with large sliding glass doors onto private terraces.
Rent one, two, three OR all four bedrooms and regardless of that number, the entire castle and staff is your's alone. No rooms are locked out to you. Grand Outlook Castle will truly be your private castle and your most memorable vacation home!
After being open just six seasons, our same guests have returned for 3, 4 & even 5 consecutive visits AND some have already booked again for 2017... so if you are interested in our very unique Anguilla experience, feel totally at ease in contacting us right away. We are licensed to offer Travel Guard trip insurance so you can be totally comfortable booking the castle well in advance.
Once you arrive at Grand Outlook Castle, you will find it hard to leave! Children and adults have been know to shed a tear when having to leave for home.
Performance granite kitchen w/ GE Monogram appliances & 5 seat bar for perfect entertaining. Hiking access to Crocus, Limestone and Famous Little Bay Beaches. Grand Outlook Castle has 99 ALL 5 STAR Guest Reviews MOST of any villa on Anguilla. Take 5 minutes & read a few. They will educate & entertain you & then ask us ANY ?'s.
The castle's views South include St Barts & St. Kitts which are 27 & 64 miles away. Grand Outlook Castle's views are amazing in virtually any direction. ALSO, you will receive the personal concierge services of Elise & Paul Grand Outlook Castle's 'Envisioners', builders and owners. They will insure your transition to Paradise is flawless. Most importantly, even if your first visit to Anguilla, you can easily and FINALLY... Come & Just EXHALE! sm This will be a simple and very relaxing VACATION!
Your BEST airfare prices? Fly into St. Martin (SXM). JetBlue flies direct from JFK, BOS & San Juan (SJU). USAirways from Charlotte (CLT) & Philadephia (PHL). American direct from Miami (MIA) and Delta direct from Atlanta (ALT)
Good local food shopping and the ability to bring frozen meat onto Anguilla from home for your personal use save hundreds of dollars... We will show you how.
1.) * Rental rates include all island fees & taxes, NO ADD-ONS and NO departure surprises!
2.) * Rental rates adjusted to the size of your group. From 2-10 guests. Regardless of you size group, you will have the castle soley for your group or family.
Safe, private & comfortably secluded. True relaxation in Paradise! OH, those views? They are 'AMAZING!'.
* Rental rates are very reasonable with the group size & seasonal adjustments.
* Staff is at your direction. Want to sleep in a couple mornings? Just let Ms. Rolyn know and she'll come by whenever you desire.
Our staff loves YOU!
You will love our staff too.
* All Grand Outlook Castle's extraordinary concierge services provided for you are at our 'COST'. Do we book vehicles for you? YES! Our best cost is your cost. Desire a pool deck massages? Do it! Our best cost is your cost.
We not only have some of the very best villa rental rates but many other ways to save you money on food, services & shopping. (Some are personal 'secrets' so you must speak with us to learn them ALL) We do like to share them with any potential guest. We make our version of True Paradise very budget friendly for you. When you and your family or group rent GOC, your nightly room cost ranges between $249 to $499 including all taxes and all fees which makes these rates the BEST!
* Washer & Dryer at the castle for your use... you do NOT need to over pack.
* Your chosen vehicles are delivered to the castle for your arrival EASY!
* Full pre-departure Anguilla information package sent to your home including a hand notated island map, recommendations and EASY castle instructions.
ALL your questions answered before you leave for Anguilla and Grand Outlook Castle. We want to answer every one of your questions so you can enjoy and explore Paradise on your own immediately UPON your arrival.
* Never rented a castle over the Internet before? *A little uneasy with the whole idea? Understandable! CALL US! *Your total peace of mind is what our goal is during you entire Grand Outlook Castle experience.
Conde Nast Traveler wrote in 2012, 'Many Caribbean islands would be grateful for just one of Anguilla’s estimated 33 powder white beaches'
Book With Confidence!! We are licensed to offer Travel Guard Insurance since 2007. A villa MUST be trustworthy to have such an approval
Elise & Paul
- Response rate:
- Response time:
- within a few hours
- Spanish, English, Italian, French, Portuguese, Greek, Italian, Portuguese & AMC, German, Spanish
- Calendar last updated:
- May 23, 2018
About Elise & Paul
In February 2003, Elise and Paul found 'Anguilla' on their very FIRST visit and knew immediately Anguilla was a very special island. ... Elise & Paul had been 'touring' the Caribbean for the 20 years' prior looking for their special Paradise. Anguilla was that True Paradise. Anugilla has the very best beaches, warmest people and numerous wonderful restaurants in all price ranges. ... Elise & Paul found the castle's site on that very first visit and actually put a deposit on the land while drinking a 'Jim & tonic' at Roy's restaurant when it was down in Crocus Bay. Elise and Paul would not have built Grand Outlook Castle anywhere else on Anguilla... Elise has sincerely noted... 'It is the grandest site we could find on Anguilla.' We bought the site in 2003 and started building Grand Outlook Castle in 2004. The Castle was completed late in 2007. OVER three years of very excellent planning and very hard labor but well worth the outcome. We have now have had over 2,500 guests in just 7 seasons and have received 87! all 5 star reviews; THANK YOU! We love it when guests say they find it very hard to leave what we were blessed in having created for your enjoyment... & ours too! Grand Outlook Castle Anguilla! As we say & sincerely mean @ Grand Outlook Castle 'COME... & Just EXHALE!' tm
Elise & Paul purchased this Castle in 2003
Why Elise & Paul chose Anguilla
Best views on Anguilla period! Serene & secluded. Plenty of room and privacy for 2-8 adults or possibly 10 with younger children. Private and safe with an actual castle tower with nearly 300* views. If unlimited views soothe you, Grand Outlook Castle is one of your best choices. Large ensuite bedrooms are spacious and comfortable. TWO with double headed OUTDOOR shower. Save time and have double the fun by showering in tandem. Large pool deck with simply massive views. A sense of being somewhere special, unique and relaxing. ALSO, as of 3/17/2015, Grand Outlook Castle Anguilla has 7.055'likes' on Facebook. When you visit, you will really 'Like' GOC ALSO! GOC always exceeds our guests expectations. Why? Because with all the pictures and all the 5 STAR reviews one MUST be at Grand Outlook Castle to understand and 'feel' the actual experience. as we say and sincerely mean... 'COME... & Just EXHALE!' tm
What makes this Castle unique
Grand Outlook Castle is so very comfortable with both large communal spaces, quiet alone places and amazing views that make it simply hard to leave. Grand Outlook Castle is located in the middle of Anguilla so getting to any beach, all major shopping and any restaurant quite easy. We are on the second highest point on Anguilla so you can see both the Atlantic Ocean and Caribbean Sea at the same time. You can see St. Barths which is 24 miles to the southeast AND on a really clear day, you can see St. Kitts which is almost 60 miles away. Being 180 feet above the sea gives viewing a truly panoramic quality. Grand Outlook Castle is a photographer's dream come true. Come and bring your camera. Anguilla is a sleepy little island named after an eel due to its shape. Twenty years ago, it began to open its eyes and realized it had no industry to promote and less to do. Locals could barely grow any crops. They had beaches and blue water, but they always had that and took it for granted. Not until outside interests were searching for virgin beaches, did Anguillans discover what was right under their noses: unrivaled beaches and ocean that surpassed any in the world. Resorts soon began to invade the shoreline: Cap Juluca, Cuisinart, Malliouhana, all five star resorts. Meanwhile, the rest of the Caribbean was building on every square inch of land with no limitations and became very commercialized. Fortunately, Anguilla has remained a sleepy island, but now the locals have jobs, employed by the resorts and their friendly demeanor reflects their gratitude for tourism. It is the ideal place for a quiet retreat, tranquil, serene, and private.Although the general dictum for an island hotelier is 'don't leave the beach', Paul Alegria followed his heart and built the newest villa on the top of a mountain in the form of a castle. Although the island is only 16 miles long and 3 miles wide, GRAND OUTLOOK CASTLE is a secret. Ask anyone on the island where it is and nearly all will
Pool / Spa
Local Services & Businesses
Sports & Adventure Activities
Check-in: 3:00 PM
Check-out: 11:00 AM
100% refund if canceled at least 60 days before arrival date. You must contact the owner directly to request cancellation.
Must return to Anguilla and the Grand Outlook Castle!
Having spent over 25 years touring Mexico and 15 islands in the Caribbean, this castle and this island are both very unique and very desirable... How many islands can one explore without having to climb over BIG mountains or around them? On Anguilla there are no mountains yet there are always stunning views? Where can you lay you head and know there is no other residence you would rather be at than Grand Outlook Castle? The castle has soul inspiring views and so many special and unique amenties that one never feels compelled to leave. Just LOVED the large private hamocks at each spectacular ensuites each providing stunning views while you are rocked to sleep by the soothing breezes... On more than one occasion, I kindly asked everyone else go out while I napped away then when I chose to awaken, I just jumped into this beautiful blue pool of perfect water sans bathing costume... There to be the only man in the world. Do visit and only then YOU can you appreciate this spectacular all senses experience!
A Magical Place on a Magical Island!
As is the case with so many beautiful homes, the pictures of Grand Outlook Castle do not do this gorgeous home justice. Driving through the gate, the Castle seems to blend seamlessly into the hill on which she sits. Lush gardens flank the driveway, and flags fly from multiple areas of the house, seeming to pay tribute to the Castle herself. Walking through the front door, one is captivated by the infinity pool and the expanse of the ocean beyond it. The only thing more impressive than the Castle herself is the vista onto which she opens. The pool deck runs the length of the house, and is appointed with loungers, umbrellas, a large patio table, and even a grille area with its own sink. One could easily spend the entirety of the vacation at the pool area! The pool itself is equally magical, with a long bench area on one side if one wishes to sit in the pool and watch the boats come in and out of Crocus Bay, below. It is also a spectacular place to watch the sun set, which we did every chance we got. The magic that is Anguilla even delivered a Green Flash to us, and the Castle was the perfect vantage point to watch the sun perform as she set. Three stories, the Castle has room for all. Each bedroom is gorgeous and gorgeously appointed, and has its own bathroom and deck. Every detail was attended to, from soap in the showers to walk in closets to each bedroom’s patio and hammock. Our room even had a small fan, which we loved because we like to fall asleep to the sound of a fan. Because each bedroom has its own air conditioning, we were able to regulate the room to the exact temperature we liked. The bathroom of the bedroom where we were, which was not the master, had two sinks (which my husband loved), a walk-in shower, plenty of light, and it even had a hair dryer. I also really appreciated the mirror that was behind the door to the bathroom – I could actually see what the back of my hair looked like! Two of the bedrooms have outdoor showers, and the master is breathtaking. The first two floors are open to the living and kitchen areas below, while the third floor boasts a very private deck which provides an incredible vista. The living room is also beautifully appointed, has a tv (who needs that though?!), and there are even paperback books with which to unwind should one wish. The kitchen is giant, and is a true chef’s kitchen. I loved sitting at the island, watching my husband (the chef of our family) do his thing. BOOK IT!
Gorgeous and relaxing
We have just returned from our 3rd stay at Grand Outlook Castle. It is a beautiful property that withstood Hurricane Irma with no issues. The grounds are more beautiful than ever and the house itself is so relaxing and accommodating, you could just stay there all day and relax with a good book! Paul and Elise took very good care of us, as usual, one call or email and they will have you on your way. Airport/ferry transport, car rental etc.
The Island has made a remarkable recovery and the Anguillan People are warmer and friendlier than ever. The beaches are beautiful, some are even larger than before and the flora and fauna are back in full bloom. We had internet and cell service everywhere we went.
Please don't hesitate to get to Anguilla this season as it is a very special season for them,
and don't hesitate to call Paul and Elise, they will make everything simple.
We had no problem getting to Anguilla. We flew in through SJU/AXA and home through SXM
Both getting there and back were flawless, no problems. The SXM airport is an experience but very efficient and all flights were getting out on time.
Sunsets, Rainbows, and Butterflys
From booking to checkout Paul and Elise made our trip carefree. The Castle really does make you feel like a King and Queen of the Caribbean. We love the massive home and expansive patio with the best infinity pool I have ever seen. Romance exudes from every corner of this place, which is unfazed by the likes of Irma. Gated and private. 4G LTE is restored island wide. Most all the great restaurants have re opened. Castle is centrally located on the island and easy to find. Daily rainbows complimented the heavenly sunsets over Crocus Bay and the mega yachts anchored below. Can not wait to return
Elise & I are so pleased to have these kind words and to have had your return to Grand Outlook Castle
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.
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!!
Dear. 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!
Elise & Paul, Katie & Gifford, Rolyn & Sue and the entire staff of Grand Outlook Castle and the people of Anguilla.
Grand Outlook Castle has been AWARDED both 'EXCELLENT RENTAL' & 'TOP ANGUILLA VACATION RENTAL' ratings for BOTH 2011, 2012 & 2013. We are blessed and so will you! NOW RANKED the #1 Villa Rental on Anguilla!!! At VRBO and HomeAway... Come and learn why... We will exceed your expectations! ***** Thank You! prior guests for having made Grand Outlook Castle such a recognized unique accomodation. ***** Grand Outlook Castle has spectacular views is very safe and very secluded with easy access to THE World's Best Beaches, great restaurants & best local stores. Nestled on the side of the 2ND highest point on Anguilla, you will be entertained by turquoise sea, beaches, sea turtles & nature. Best SUNSETS & embracing VIEWS are YOURS! **** 4 huge ensuite bedrooms provide privacy w/ large baths & each with big balconies. Grand Outlook Castle uniquely provides you with constant awe. Guests seldom need or want to leave. Cook in our SPACIOUS kitchen, grill by the pool or schedule our chef for a luxurious evening. ***** At GOC, your hardest decision IS when to break from its embrace. We arrange adventures, spa and dining so you won't have to make those decisions. Our staff is available to answer all questions whether it's your 1st or 10th stay. Guests exclaim... ''Best Vacation Ever!'' & A 'MUST return'. Our Castle is amazing! You will BE a HERO for booking Grand Outlook Castle. We NOW have 48 5-STAR REVIEWS! Most on AXA! Other Activities: RELAX! on the World's Best Beaches from one of the World's Best Views!!! Beaches are either a walking hike away or a short ride. Driving on Anguilla is easy as the island is quite flat... Grand Outlook Castle is within walking distance to the NEW! Pelican Trail & Water Sports at Little Bay. Serving food & drink, breakfast, lunch & dinner. Glass bottom kayak rentals, sea trampoline and guided tours of the coastline. Also, very easy access to famous Little Bay Beach by Calvin's boat down at Crocus Bay Beach. You can also walk to both Koal Keel and beachfront DaVida restaurants and enjoy wonderful views the entire way. Golf: JUST 10 minutes from Grand Outlook castle, the Cusinart Golf Course has been rated the #3 course in all of the Caribbean. Greg Norman designed course with beautiful views during your entire round with many exciting and challenging holes. Five t-boxes per hole allows you to play the course at a variety of different skill levels. EVERYONE can play on this beautiful BUT very low key golf course. There is no rushed t-times and no marshalls unless they are bringing you refreshments. It's a wonderful course to bring friends or family to play and truly enjoy a round of golf together even if their games is a challenge. 18 holes Driving Range Putting Green Carts Caddies Par 72 slope 75.6/134 Black Tees play 7,063 yards Gold Tees play 6,673 yards Silver Tees play 6,243 yards Copper Tees play 5,772 yards Jade Tees play 5,317 yards *** This golf course was designed so ALL levels of players can enjoy a relaxed and stress free round of golf TOGETHER in PARADISE! Come play great golf on a great course from a great castle... Grand Outlook Castle
Rates & Availability
Additional information about rental rates
Grand Outlook Castle's rates include all fees and taxes. There are no additional charges from the rates you are quoted by the owners. Quotes here are only estimates and require owner verification. Services from chefs to massages or fresh fish to fresh herb are available on an ala carte basis. Most Grand Outlook Castle base rates are for 2 bedroom use and four guests with a minor charge of