Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

$10,000USD in FREE! travel insurance coverage* NO WORRIES!-RATES NEGOTIABLE-EASY

Bedrooms 4
Half Baths1
Space 7,222 sq. ft.
Property type castle
Minimum Stay 5 - 7 nights


About the property

"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...


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

More Details

Elise & Paul
Member since: 2004
Speaks: english, french, german, spanish, portuguese, italian, English, Greek, Spanish, Italian, Portuguese & AMC
Response time:
Within a few hours
Response rate:
Calendar last updated:
February 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 The Valley

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

Guestbook comments from the owner

We, at Grand Outlook Castle, just received this e-mail from Judy who stayed at the castle during November 2013. Her words speak for themselves. THANKS Judy!

Hi Paul,

Just wanted to drop you a quick note. Just returned from Mexico, even though

it is so easy to get there and there is no cooking, we all agreed our time at GOC was absolutely our favorite vacation ever!

Nov 2013
  • 1 of 8


The Valley Castle Accommodation and Amenities

Property Type:
  • castle
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 7222 sq. ft.
House Rules:
  • Check-in: 3:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 10
  • Events Allowed
  • children welcome ...
  • pets not allowed
  • non smoking only ...
Location Type:
  • Beach ...
  • Beach View ...
  • Beachfront ...
  • Downtown ...
  • Near The Ocean ...
  • Ocean View ...
  • Oceanfront ...
  • Rural ...
  • Water View ...
  • Waterfront ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning ...
  • Alarm Clock
  • Broadband Access ...
  • Ceiling Fans
  • Clothes Dryer ...
  • Filtered Water
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Mobile Phone ...
  • Parking
  • Parking Off Street ...
  • Safe
  • Security System
  • Telephone ...
  • Thermos Bottle
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • 4 Ring Stove
  • Blender
  • Catering Available ...
  • Coffee Grinder
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils
  • Dishwasher ...
  • Freezer ...
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 10 people
  • 4 Bathrooms
  • 1 Half Bath
  • Main Floor - toilet , HALF BATH OFF KITCHEN
    2nd South - toilet , shower , Huge bath & LARGE indoor shower with no door or curtain OPEN
    Master - toilet , shower , outdoor shower , double headed OUTDOOR shower with beautiful ocean views.
    1st South - toilet , shower , outdoor shower , double headed OUTDOOR shower with Great views! A favorite
    1st West - toilet , shower , Huge bath & indoor shower with window onto bananna trees
  • This unique bathroom flows directly from the bedroom area and allows easterly breezes to sweep through the bedroom. Double headed outdoor shower can truly double your fun. Double vanity allows each guest to have plenty of work and storage space. Plenty of light in this and all our bathrooms as we designed the lighting to be cool during the day but like a Broadway Opening at night. Most of our light fixtures are on dimmers. 'How can you get your mascara correct unless you have enough light?' Elise lamented when we rented elsewhere on Anguilla. Electricity is so expensive on the island that many location keep lighting to a minimum but not at Grand Outlook Castle. ***Photo Credit... Main sunset photo by Mr. Michel Istaphanous
  • 4 Bedrooms, Sleeps 10
  • 1st West - 1 king , 1 child bed , Another Very Large ROOM 11' CEILINGS & private deck hammock!
    1st South - 1 queen , 1 twin/ single , Very Large w/11' CEILINGS & 2 sliders to pool and hammock!
    Master - 1 king , 1 baby crib , Very Large ROOM w/ 15' CEILINGS and private deck & hammock
    2nd South - 1 queen , 1 twin/ single , Very Large ROOM 15' CEILINGS best views to the sea
  • ALL 4 Master Bedrooms with both sunrise and sunset patios. One for morning sun the other for the evening sunsets. Views from ALL bedrooms are breathtaking and you can see well about the island. Ceiling fan and fully air conditioned for your comfort as all our bedrooms are. This bedroom is actually is 78 feet in length from the end of one patio to the other; you could walk laps in this room! King size bed with chair and a chair with ottoman. A great bedroom to read and relax! Outdoor shower has two separate heads and water controls. No one gets cold and you can comfortably entertain while watching the sunset, expansive view or stars. Two large walk-in closets for plenty of storage space during your stay. Armoire has 26' Plasma TV and extensive DVD library. The TV is there but... you don't have to be exposed. Our staff can create any configuration you choose; full TV & Video, Video only OR neither at all. PLEASE CALL FOR YOUR SPECIAL DATES!!!
  • Books
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Video Game Console ...
  • Video Library ...
  • Balcony ...
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Binoculars
  • Crow's Nest
  • Deck / Patio ...
  • Gated Community
  • Golf
  • Lanai / Gazebo ...
  • Large Cooler
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Screen Porch / Veranda
  • Small Cooler
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • 14 garden chairs
  • 8 beach chairs
  • Groups
  • Long-term Renters Welcome
  • Low Allergen Environment
  • alternative lifestyle
  • suitable for elderly or infirm
  • wheelchair accessible ...
Pool / Spa:
  • Outdoor Pool
  • Private Pool ...
Onsite Services:
  • Car Available
  • Car Optional
  • Chauffeur
  • Concierge
  • Massage
  • Private Chef
  • Staff
  • bay/sound
  • botanical garden
  • caves
  • churches
  • duty free shops
  • festivals
  • forests
  • health/beauty spa
  • marina
  • museums
  • nude beach
  • playground
  • pond
  • recreation center
  • reefs
  • restaurants
  • ruins
  • synagogues
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • gambling casinos
  • horseback riding
  • paddle boating
  • scenic drives
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • kayaking
  • mountain biking
  • paragliding
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • spelunking
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Grand Outlook Castle comes with everything you will need and those items you don't are available. Children are welcome and we provide a Safety Turtle pool alarm and a secure play area just off the main deck. First floor living is easy for the elderly members. First floor bedrooms have level access to the pool, outdoor grille/dining areas, living room with three steps to the kitchen/dining areas. Communication! Very important when you are a distance from home. You have castle wide WI-FI access. Plus, The Castle comes with an international cell phone. You can receive and make calls anywhere on the island. Rates per minute to the US are very reasonable at $.336 day, $.299 evenings & $.261 on weekends. It's a pay as you go phone so you can easily manage your cost by only adding the money you want to spend. Money runs out, no calls go out but all incoming calls are Free! It's saved us hundreds of dollars!! We do ask and require ALL smoking MUST be conducted outdoors. PLEASE CALL FOR DATES!


Exceptional! 5/5 -
(132 traveler reviews)

100% Complete
0% Complete
0% Complete
0% Complete
0% Complete
$10,000USD in FREE! travel insurance coverage* NO WORRIES!-RATES NEGOTIABLE-EASY
average rating of 5.0 based on 140 reviews

Grand Outlook Castle amazes again!!

  • 5 of 5

Even on our 3rd trip The Castle must be seen and visited in person to understand the beauty. The ocean views and watching sea turtles surface below never gets old. The villa has everything to make this your home away from home. The kids kept saying 'when we come next time...." let's you know this is a forever vacation place. All of the staff go above and beyond to make your stay fantastic. Paul and Elise give you so much information, insider tips and deals to make it so easy for you. We feel like locals when we are here. And we definitely will be back again!!

  • Submitted: Sep 26, 2017
  • Stayed: August 2017
  • Source: HomeAway
Owner's Response: WOW!!! Donna... Elise and I are both crying. You are so kind and we hope your message of optimism and connection to Anguilla gets out for all of Anguilla. THANK YOU!!! is truly not enough. Elise & Paul The staff, neighbors and colleagues on Anguilla at Grand Outlook Castle! Treat other as you would want to be treated yourself! TGYC!
Did you find this review helpful?
3 0

Sunsets, Rainbows, and Butterflys

  • 5 of 5

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

  • Submitted: Jan 26, 2018
  • Stayed: January 2018
  • Source: HomeAway
Owner's Response: Hello Bobby, Elise & I are so pleased to have these kind words and to have had your return to Grand Outlook Castle
Did you find this review helpful?
0 0


  • 5 of 5

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.

  • Submitted: Dec 26, 2017
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 0


  • 5 of 5

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!!

  • Submitted: Nov 20, 2017
  • Stayed: October 2017
  • Source: HomeAway
Owner's Response: 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! TGYC! Elise & Paul, Katie & Gifford, Rolyn & Sue and the entire staff of Grand Outlook Castle and the people of Anguilla.
Did you find this review helpful?
1 0

Awesome Memories Made at the Castle!

  • 5 of 5

My wife and I have stayed at many villas throughout the Caribbean over the past 30 years and we have stayed at other properties on Anquilla. This was the first time for us to stay in the Castle. We had an awesome time with another couple celebrating our 36th wedding anniversary and 60th birthdays for 3 of us! It was an incredible experience that gave us many lasting fun memories that we will not soon forget.

The Castle is an incredible property, with spacious living areas, bedrooms, kitchen, and pool deck areas. The views are spectacular! The kitchen is so well equipped that we ended up canceling most of our dinner reservations and preparing our meals at the Castle so we could continue to enjoy the views. The Best Buy Grocery had everything we needed to prepare some fabulous meals. Two of the bedrooms have awesome double outdoor showers, and those are the rooms we utilized during our stay. We loved them!

The internet worked better than my internet back home in the US, and we had no problem using our iPhones for several important calls back home using the wifi internet phone capability on our iPhones. The sound system provided great sound out by the pool, where we spent most of our time, watching the boats come in and out of Crocus Bay.

We used Calypso boat charters for a day trip to Sandy Island for lunch, and we had a blast. We also used Calvin who sits under a tree at Crocus Bay to take us over to Little Bay for some great snorkeling one afternoon. We went for walks almost every morning which was a great way to start the day!

Rolyn, the housekeeper, was very friendly and helpful. Paul and Elise were delightful to work with, even assisting with arrival and departure forms, ferries, and car rentals. Everything was fantastic, and we would not hesitate to recommend this property to our family and friends. We look forward to our return visit to the Castle!!

  • Submitted: May 2, 2017
  • Stayed: April 2017
  • Source: HomeAway
Did you find this review helpful?
3 0


  • 5 of 5

We dad a fantastic week at GOC.the villa and kitchen was very well equipped ,and we spent ️️lovely evenings dining at the poolside.the staff were most helpful ,making sure that we had everything that we needed to have a perfect holiday.the pool was lovely to relax in ,looking down onto the beach below .i especially loved the outdoor showers.

  • Submitted: Apr 19, 2017
  • Stayed: March 2017
  • Source: HomeAway
Owner's Response: Hello Jayne, Happy to have your most kind words on your group of 8's retreat to our version of True Paradise, Grand Outlook Castle. Yes, we did design the castle to accommodate multiple chefs in a large performance styled area. AND we leave many spices and some beverages behind for easy assimilation to your castle culinary fun. We have an idea why you "especially loved the outdoor showers. When we designed the outdoor showers Elise and I wanted it to be a "performance style area" like the kitchen but a tad more intimate. So, each of the castle's outdoor showers has TWO shower heads... See what I mean? As we like to say at the castle, "save time, have fun and shower together" comfortably AND isn't that what vacation is all about??? CHEERS & THANKS! Elise & Paul The Grand Outlook Castle TGYC!
Did you find this review helpful?
3 0


Nearest Airport
1.6 Miles
NEW Clayton International Airport on Anguilla
Nearest Barpub
1000 Metres
DaVida on the beach just below GOC
Nearest Ferry
3.2 Miles
Blowing Point Ferry
Nearest Golf
3.5 Miles
Cuisinart Golf, Rated 3rd best in Caribbean! OPEN
Nearest Motorway
150 Miles
No such thing on Anguilla... Fortunately!
Nearest Restaurant
1000 Metres
DaVida restaurant, walking distance free loungers
Nearest Beach
1000 Metres
World Famous Little Bay short hike-Calvin's boat
Car: recommended

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




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

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.