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.

Spyglass Hill Villa

Save
Want exclusive deal alerts, booking reminders, and quicker checkout?
Log in now
Spyglass pool deck
Overview
Reviews
Amenities
Availability
Map
Policies
Overview
4 bedrooms
5 bathrooms
8 guests
Min stay varies
The minimum stay for this property changes depending on the dates selected
Villa
Spyglass Hill Villa - A private four-bedroom luxury villa overlooking the Caribbean Sea on the idyllic island of Anguilla. Perfect for a couple, family or group of friends. Perfect for a couple, family or group of friends. Spyglass Hill Villa offers all of today's modern conveniences in a traditional West Indian setting. We invite you to rediscover your senses in Anguilla in the tranquillity and seclusion of our intimate tropical setting and breath-taking vistas. The four bedroom Anguilla villa is perched on the ridge at North Hill overlooking Road Bay harbour and offers stunning views of the Caribbean Sea, the surrounding islands, nightly tropical sunsets and the quaint village of Sandy Ground below. Spyglass Hill Villa captures the essence of Caribbean style and design with i...Spyglass Hill Villa - A private four-bedroom luxury villa overlooking the Caribbean Sea on the idyllic island of Anguilla. Perfect for a couple, family or group of friends. Perfect for a couple, family or group of friends. Spyglass Hill Villa offers all of today's modern conveniences in a traditional West Indian setting. We invite you to rediscover your senses in Anguilla in the tranquillity and seclusion of our intimate tropical setting and breath-taking vistas. The four bedroom Anguilla villa is perched on the ridge at North Hill overlooking Road Bay harbour and offers stunning views of the Caribbean Sea, the surrounding islands, nightly tropical sunsets and the quaint village of Sandy Ground below. Spyglass Hill Villa captures the essence of Caribbean style and design with its relaxed and rejuvenating indoor-outdoor living spaces. This residence is inspired by a large indoor atrium and features the natural warmth of wood throughout, from our authentic bamboo floors to our round log roofs and our beach driftwood decor. Outdoor living options abound at Spyglass Hill Villa. The open-air courtyard offers a warm welcome to the villa and brings the refreshing outdoors inside. Travertine brick pavers and the hand-carved Anguilla stone walls add to the elegant but cozy ambience. An infinity-edge pool gives the illusion of cascading water into the Caribbean Sea while the large pool deck provides several options for lounging by the pool, entertaining or dining under the stars.More
House Rules
Pets Allowed: No
Smoking Allowed: No
Kid Friendly: Yes
Bathrooms
4 Full baths, 1 Half bath
Show more
Meet the host
Janine E
Hosting since November 2009
Languages spoken: English, Spanish
Response Time: Within a few hours
Contribute
Reviews (14)
Number9of9
Number9of9
2 contributions
We arrived just in time to catch a magnificent sunset and enjoy a beautiful breezy evening on the patio with friends. The villa is set up with every comfort for a carefree vacation; fully stocked kitchen, airy bedrooms and plenty of comfortable spaces to sit and take in the views. Our kids especially appreciated the WiFi(!), the great sound system and the infinity pool. The staff took wonderful care of us from the initial booking throughout our stay and made sure that we had everything we needed. Spyglass Hill Villa, Anguilla is the perfect spot to get away from it all, and we're already planning to return!
Visited March 2019
Written 29 March 2019. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Greetings Trish, The Spyglass Hill Villa team were delighted to host your wonderful family and we are happy that you had a memorable time in Anguilla. Warm wishes across the seas…hope to welcome you back again soon!
Written 4 April 2019. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Findlay Q
Findlay Q
Vancouver, Canada32 contributions
We rented spyglass for a month starting nov 8 to dec 10 2018 . We had 3 adult couples for the first 2 weeks and 3 adult children and 3 grandkids for the second 2 weeks. We have travelled extensively in the Carribean renting homes on other islands . Anguilla and Spyhill were by far our best experience. The home is everything it is represented to be . Beautiful views . Perfectly equipped from kitchen to entertainment ( the little gym is a great bonus).the way the home is designed allows complete privacy for everyone . Bedrooms are large with well appointed bathrooms and spectacular decks . Beds and linens are perfect . There are 4 separate common areas where you can gather or hide depending on your mood all wonderfully furnished . The pools is everything the photos show it to be . We partied with adults late night in the pool and 2 weeks later were in the pools with our grandkids . The most enjoyable part of this property however is the service.thw owner Janine is a smart ,attentive hospitality pro . Any communications are responded to immediately and any issues resolved within the half hour(literally). She actually sends you daily ideas of what is happening on the island! The daily cleaning service provided by Shelly and Onika is beyond any expectation. On the day before our grandkids arrived they stayed and extra 3 hours polishing the place though it was already spotless. From arranging transport from st martin airport , to greeting us at the ferry ,to arriving to a fully stocked fridge and bar ,to having rental cars delivered to the house .... this place is dialed in A few other thoughts: Anguilla is a complex place for such a small island . The home is located on north hill and feels remote when you arrive . Your first thought is that it is too isolated . However after a couple of days of driving around the island ( and you need a car in Anguilla if you are really going to enjoy it)you realize the location is perfect .every morning we got up, had breakfast , went for a swim or the gym or both then headed out on an adventure . Spy hill is literally less than 20 minutes from everywhere:shoal bay east beach and the spectacular madearimans beach restaurant; rendezvous bay and coconuts and bankys (especially Sunday) ;meads bay and waves beach shack ; Saturday night in the valley at KEN’s bbbq; sandbar in sandy ground.... just to name a few . Anguilla is not a place you want to go and sit in one place .
Visited November 2018
Written 10 December 2018. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Guvnors
Guvnors
Mill Neck, NY5 contributions
My family and I returned to Spyglass for the Holidays. We had the most wonderful time. Anguilla is back !! Spyglass Villa even more beautiful! New furniture in dining room, living room and bedrooms. The gardens very well manicured and amazing views from every area! Anguilla beaches are beyond stunning but sometimes my family of six adults and I wanted to relax at the villa to swim in the infinity pool and gaze at the stunning views. Spyglass is set high on a hill with spectacular views of the ocean and Sandy Ground. The housekeeping by Shelley is to the highest standard. Nothing too much trouble for Shelley, who goes beyond the call of duty to make everything perfect for us. Mrs. White catered dinner on arrivals day, which was greatly appreciated. Delicious fish and the cheese and potato pie was incredible!! Such a special place to stay, we can’t wait to go back!!
Visited December 2017
Written 23 January 2018. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Guvnors
Guvnors
Mill Neck, NY5 contributions
My husband and I travelled Anguilla for the first time with our sons (20, 22)and a friend for spring break. Spyglass Hill Villa was highly recommended by a family member and did not disappoint. We flew to St Maarten and hired Calypso Charters to take us to Blowing Point Ferry Terminal. Captain Tony and Zeek were friendly and offered us refreshments and we immediately relaxed and felt our vacation had begun. Zeek gave us information about Anguilla and told us about the famous Moonsplash Music Festival. We were met at the ferry terminal by Mrs. White who took us to Spyglass and showed us around the beautiful villa and gave us valuable details about restaurants ,beaches and fun excursions. We were all blown away by the breathtaking views from every room. Everything was exceptionally clean and tidy. The kitchen was well stocked with all our recquests and a delicious lunch prepared for us. A generous bar stocked with everything you could possibly want for vacation cocktails. Shelly did an outstanding job housekeeping. Everyone extremely friendly,helpful and kind. We hired a car for the week and visited many beaches and restaurants. We loved all the beaches! Blanchards Beach Shack was great for lunch. Dinner at the restaurant next door was amazing too. Tropical Sunset at Shoal Beach was delightful for lunch, delicious food beautiful beach, snorkeling and bird watching. The pelicans diving for fish was mesmerizing. Junior was there too, great guy who will take you out in his glass bottom boat for a fun snorkeling plus excursion. Sunshine Shack, Rendezvous Beach was great. A day out on Sandy Island is amazing, probably our best day. Not to be missed. At the end of every beach day we all loved to walk into Spyglass villa and hang out there with cocktails. We loved the courtyard, the central part of the house and the lovely patio with comfy chairs/sun beds and hammock. We loved our experience in Anguilla so much we plan to go back soon. We have more to discover.
Visited March 2017
Written 21 March 2017. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Bdub
Bdub
Cornelius, NC35 contributions
We stayed at Spyglass Hill Villa the week of New Years. It exceeded all of our expectations. Ms Janine was fantastic in communicating with us all the way up to the trip. She answered every question that we had and was extremely accommodating and helpful. The villa was more than we expected. Ms Erlene was so helpful once we got there and met us at the port. She showed us the house and made sure we were well taken care of the entire stay. Ms Shelly was an amazing housekeeper. Service as better than any resort! They go out of their way to make you feel at home and to be sure you have all the comforts that you could possibly need. If you are considering a villa for your stay, this is the one. Reasonably priced, great location, incredible views, and the house is extremely nice.
Visited January 2017
Written 6 January 2017. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Dear Brian, Thank you again for choosing Spyglass Hill for your vacation. We are happy that your time was well spent on Anguilla and your stay with us exceeded your expectations. Reviews like these makes our day and Shelley and Erlene was happy to read. We do take pride in providing that warm hospitality for our guests. Grateful for your kind sentiments and would be our pleasure to host you again.
Written 22 March 2017. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Alexandra O
Alexandra O
New York City, NY14 contributions
How do I sum up the most perfect week away? I'll start by saying that from the moment we first contacted the Spyglass Hill team, we knew we would be in great hands... but we never could have imagined the extent of it. Upon arriving at the Blowing Point ferry, we were met by Erline who coordinated our transport to the villa. Once at the villa, we were immediately blown away. Photos just can't do this house justice. The views are amazing. The bedrooms are large and beautifully decorated with incredible outdoor showers on the 2nd floor, Our grocery shopping had already been completed. The car rentals were in the driveway. And a Christmas corner had been set up in response to our request for some lights on a tree. What's more, Shelley was there to greet us with rum punch and assorted sandwiches. For eight wonderful days, we were treated with such warmth and hospitality -- anything we needed, they were quick to provide or address -- including recommendations, reservations, and even a surprise birthday cake for my dad. Plus, the house is located in the center of the island, making it a 7 minute drive to Sandy Ground, and a max of 15-20 minutes to most anywhere you want to go (33 white sand beaches to choose from, each with clear, turquoise waters!). Janine, Erline, Shelley - thank you for making this the most perfect vacation! We look forward to visiting again soon.
Visited December 2016
Written 29 December 2016. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Dear Happy Guests, I believe you've summed it up well and thank you again for choosing to stay with us for your vacation. We are happy that you enjoyed Anguilla and your stay with us and it was a pleasure hosting you. We are really grateful for your kind sentiments and feedback and hope to have the pleasure of hosting you again soon.
Written 22 March 2017. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

CJTheJetsetter
CJTheJetsetter
St Martin / St Maarten7 contributions
My stay at spyglass with my team back in June 2015, has been an amazing experience. The breathtaking views, the modern approach to vacation luxury and so much more is wrapped up in this property. I will always recommend it to the travelers i am in contact with as well as i look forward to returning in the near future! Thank you Spyglass team!
Visited June 2015
Written 18 October 2016. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Hello CJTheJetsetter, you're very welcome and thank you for sharing your experience at Spyglass Hill. Happy that you enjoyed the villa that much. We'd love to have you again.
Written 22 March 2017. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Ryan H
Ryan H
1 contribution
We stayed at Spyglass Hill Villa in May 2016. The house and the view are both gorgeous. Even better than the pictures online. When we arrived in Anguilla a representative for the house was waiting for you us at blowing point ferry terminal who escorted us to the villa. When we arrived they had lunch in the oven keeping warm that they picked up for us from a restaurant included in the price of our stay. They had also stocked up the pantry and fridge with way more than expected free groceries. They had asked when we booked for a list of snacks we liked. Not only did they have all the snacks we listed, but they had dozens of other unopened groceries. Also when we arrived we found our rental car waiting for us in the driveway. The villa comes with a cell phone that you are allowed to take with you around the island to make calls from. The villa also has two landline phones: one for free local calls and one for free calls to the US. In the garage we found rafts and pool toys that could be used pool. The kitchen is fully stocked with all plate and glassware you could need as well as pots, pans, cooking utensils. Etc. All 4 rooms in the house could all be considered master bedrooms since all four rooms are large and come with their own full bathroom. We found all the rooms to be very clean. The 4th bedroom which is underneath the main floor of the villa is more like an apartment than a bedrooms. It's also has a pool table, small gym, kitchenette, and living room. The house also has an automatic gate that you will get a clicker to so you can feel safe that no one is getting in at night. There is air conditioning in each bedroom that works very well but you may not even need it depending on the time of year. Due to the house being up on a hill, you get a wonderful cross breeze when the doors are opening that surprisingly cooled us off even when the AC was off. We really could not come up with one complaint about our stay here. We were blown away by every aspect of Spyglass from the time we arrived till the time we left
Visited May 2016
Written 8 June 2016. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Thank you again for choosing to stay with us. We appreciate you taking the time to provide us with such detailed feedback about the property and experience. It makes us here at Spyglass very proud of our vacation offerings, and we look forward to continuing to offer luxury, comfort and warm hospitality. We would love to host you again. Until then. Take care.
Written 9 June 2016. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Kevin A
Kevin A
8 contributions
Beautiful spot above Sandy Ground. House was delightfully laid out for 4 couples. Enjoyed watching the activity in the harbor. Great location for hopping around to different resorts but better than all of them. Shelly was terrific supporting the house and was a great source of info on restaurants snorkeling etc. Would absolutely choose the same house.
Visited March 2016
Written 19 March 2016. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
NorthStar540873
NorthStar540873
Greetings from sunny Anguilla. Thank you for choosing Spyglass Hill for your vacation and really appreciate your feedback. Happy that you enjoyed your stay here and Shelly would be pleased to know that her service to you was well accepted. Looking forward to seeing you again.
Written 9 June 2016. This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Carla A
Carla A
Portsmouth, Dominica1 contribution
Oh my Gosh, a girlfriend and I recently escaped to Anguilla and Spyglass Hill Villa on a moment's notice to rest and relax and enjoy great food. From the moment we arrived at the airport we felt like royalty, Ian the owner greeted us and took us to Spyglass. Being handed fresh chilled almond scented facecloths to wipe away our days travels was just the beginning, with the sun just set the sky glimpsed through from the entrance gate was ablaze and the twinkle of the lights in the bay below were already dancing in the distance. Settled in each of our Master suites and shown around including the intro to a fully stocked bar and fridge was enough to make us want to just lose ourselves then and there, little did we know, as we were ushered to get changed and back in out that the first dinner Ian had reserved for us at Cuisinart was a taste of the next 4 days. Daily meditation, long runs along craggy hillsides, beaches and village roads, daily Pilates on the deck next to the infinity pool and every little detail seen to, I honestly had a hard time tearing myself away to return to reality. All in all it was really an amazing experience that I dream about too often and think,... who needs a royal title when you're in Janine & Ian's care at Spyglass Hill Villa anyway?
Visited November 2014
Written 18 December 2014. This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Showing results 1-10 of 14
Amenities
Pets Allowed: No
Smoking Allowed: No
Kid Friendly: Yes
DVD Player
Air Conditioning
Balcony
Grill
Ceiling Fans
Deck
Dishwasher
Dryer
Refrigerator
Gym
Internet Access
Hot Tub
Microwave
Mountain Views
Patio
Private Outdoor Pool (Unheated)
Private Garden
Safe
Cable/satellite TV
Secure Parking
Stereo System
Cooker
Terrace
Toaster
TV
Washer
Water Views
Wi-Fi
Fishing Nearby
There Is A Golf Course Within 30 Mins Drive
Horse Riding Nearby
There Are Tennis Courts Nearby
Watersports Nearby
See more amenities
Availability
M
T
W
T
F
S
S

February 2023

M
T
W
T
F
S
S
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
1
2
3
4
5

March 2023

M
T
W
T
F
S
S
27
28
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
Map
+
Access
Car advised
Activities nearby
Fishing Nearby, There Is A Golf Course Within 30 Mins Drive, Horse Riding Nearby, There Are Tennis Courts Nearby, Watersports Nearby
Cancellation Policy
  • 100% refund within 24 hours after booking (provided the stay is at least 60 days away).
  • 100% refund* if you cancel at least 2 weeks before check-in
  • No refund available if you cancel thereafter

Enter your trip dates to see an exact cancellation policy.

*Booking fee is excluded from refund amount

About this property

First, check the Availability tab on this page to see if your dates are available. If they are, contact the owner via the Tripadvisor Rental Inbox to confirm availability.

Initially, you may contact the owner via the Tripadvisor Rental Inbox. This inbox is created after you send your first message or booking request to the owner. After you've made your first payment, you'll be able to see the owner's contact information.

This owner will contact you via the Tripadvisor Rental Inbox.

You can send another message via the Tripadvisor Rental Inbox to ask if the property is still available.

For this property, please use a credit card to pay via the Tripadvisor Rental Inbox. Once the owner approves your stay, he or she will send you a quote, which will include payment instructions.

Yes. Payments made via the Tripadvisor inbox are covered by our Peace of Mind Protection.

Still can't find what you're looking for?
Do you own a holiday home? 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
#FKN2224301010
Frequently Asked Questions about Spyglass Hill Villa

Spyglass Hill Villa is able to accommodate up to 8 guests. See all property details.

Spyglass Hill Villa has 5 bathrooms available. See all property details.

Spyglass Hill Villa has 4 bedrooms available. See all property details.