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HomeAway is the world leader in vacation rentals. We offer the largest selection of properties for any travel occasion and every budget. We're committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together.

    #1 RENTAL VILLA & $10,000USD w/ travel insurance included* NO WORRIES 4 U!

    Valley, Anguilla
    • Castle7222 sqft
    • Bedrooms4
    • Sleeps10
    • Bathrooms4
    • 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

    Owner

    Elise & Paul

    Member Since 2004
    Response rate:
    100%
    Response time:
    within a few hours
    Speaks:
    english, french, german, spanish, portuguese, italian, English, Greek, Spanish, Italian, Portuguese & AMC
    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

    $885avg/night
    135 Reviews
    Exceptional 5/5
    Enter dates for accurate pricing
    For booking assistance, call 888-640-7927

    Property # 167080

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