Anguilla Villa Rental

Everything you want to know about an Anguilla luxury villa for rent! Below is what what we have learned over the years about villa rentals. Now that we’re owners, we have an inside knowledge of how it works and can offer suggestions, for what to look for as you search for an Anguilla villa rental or for a villa rental with chef, and how to get the best price. When you decide to search for villas in Anguilla, perhaps keep some of these thoughts in mind….


Jon and I have visited many islands and villa rentals and have been disappointed. When we built the Bird of Paradise, we knew exactly what we wanted the architect to include in his design with the most important feature being “no one is cheated”. Everyone has a master suite with an equal view of the beach and the Caribbean. As you look at Anguilla villa rentals, check out whether there’s only one master suite. Do the guest rooms have a view? Does everyone have a veranda? How do the bathrooms compare? This is especially important when couples are traveling together and are sharing in the cost of the villa.

There are a lot of villas which are put together with second-hand furniture. Usually, you can tell from photos the quality of the interior design, bedding, amount of clutter, etc. Are you just looking for a roof over your head or do you want that ‘WOW” factor for a special vacation or celebration? The Bird of Paradise design firm has also designed Armani and Ritz Carlton resorts. The Bird of Paradise has won awards and been featured on the cover of magazines for its design and ambiance.


There are villas in Anguilla which say they are beach front, but they have only a spit of man-made beach or a rocky, un-swimmable waterfront property. Worse is when they show photos of an Anguilla beach making you think it’s near the villa when it isn’t. Bird of Paradise is at Sandy Hill Bay, which is a long crescent beach with no resorts or restaurants, so very private. As you’ll see at our link, “beach hopping” is one of our favorite activities on Anguilla, so we encourage our guests to explore. Anguilla is only 30 square miles with 32 beaches. We hope you have the time to find them all!

Note, there are quite a number of villas on Anguilla which are at the ends of long, unpaved dirt roads. You don’t want to spend your vacation changing tires. We appreciate the fact that Bird of Paradise is easily accessible, but very private and secure.

What's Included in an Anguilla Villa Rental? 

Be sure to compare apples to apples when you’re comparison shopping.The villa website should have a list of exactly what's included as far as staff, technology (TVs, WiFi), A/C, DVD library, kitchen equipment, beach toys, picnic baskets, games, etc. We had a friend who had an Anguilla villa rental for the summer and arrived to discover there was no A/C in the bedrooms! See the link below for a complete list of staff, services and amenities available at the Bird of Paradise. Depending on your budget, we can add chef, butler, car and driver, rental car and more.

Services and amenities

More information follows below regarding chef services, but beware of “breakfast included” as you compare Anguilla villa rentals. Usually this means nothing more than the housekeeper starts the coffee pot and puts out rolls. At the Bird of Paradise our packages include a proper chef with a full American-style breakfast.

Is the Pool Heated? 

Are you like me and you don’t want to get in water unless it’s 85+ degrees? Don’t assume a pool is heated. Electricity for a four-bedroom house can run $4,000+ US per month on Anguilla and water can cost another $1,000+. There are very few villas that heat their pools. They may say they have solar heating, but are they talking about just the sun or solar panels? Bird of Paradise has two pools and more than 30,000 gallons of gas-heated water. A warm pool is especially nice when traveling with young children.

With Whom are you Talking? 

One of our greatest sales points, I've been told by guests and travel agents, is that when they book the Bird of Paradise they are talking directly with me, the owner. Who knows the property better than the owner? Who has the power to adjust rates? We have four sample packages as described below, but as the owner I can customize a package for your Anguilla villa rental based on your budget.

When to Travel to Anguilla?

The cost of our Anguilla villa rental varies depending on the time of year/season. You can definitely save big bucks by coming May 1 to November 14. The weather is great, but most Anguilla villas have pricing close to their cost of operation. 

The most expensive time to visit Anguilla is over Christmas/New Year’s. We turn away dozens of people, and I always encourage them to celebrate the holidays early or late and save tens of thousands of dollars.

Cost for an Anguilla Villa Rental

You can rent a summer home in the Hamptons for $250,000 and not even get a roll of paper towels, and definitely no staff. Anguilla's Bird of Paradise in contrast offers all the staff and amenities of a 5 star hotel, including access to a chef, for a far lower price, which we can do because there’s no middle man, and you’re dealing directly with the owner. The villa has all the comforts and spaciousness of an executive home, but amenities such as Bulgari, Italian linens and bathrobes, concierge, daily housekeeping and a beach attendant. 

The most expensive all-inclusive villa on Anguilla is 9 bedrooms and it rents for $25,000/day plus 10% tax and 10% service charge. There’s a list of luxury villas with 4-6 bedrooms in the range of $5 to $6,000/night in high season plus the tax and service charge. Most have no chef included in these prices. Based on location, ambiance and services, this is our competition, but at the Bird of Paradise our prices are considerably lower.

We believe the Bird of Paradise offers the best value for a 5 star villa, the reason being that, again, Jon and I are doing our marketing and there’s no middleman. Our daily rates vary from $1,480/night for two people in low season with our “basic” 5 star package to $4,100/night for 10 guests and our “platinum” package in high season, which includes a full-time chef, butler, rental cars and more. Pricing for this Anguilla villa rental depends on the time of year as mentioned above, but, also, number of guests. If it’s a small group, we give back our savings in housekeeping and utilities. Some villas have one price no matter how many guests.

We’re unusual in offering options to guests. We do not have a “take it or leave it” attitude. We can customize services to fit your budget. One guest told us about a former Anguilla villa rental which included a chef for breakfast and one meal per day. They were irked that they had to pay for this chef and staff even though they chose to go to beach bars for lunch or enjoy fine dining atlocal restaurants on a night or two. As you comparison shop, check the flexibility of the villa as it pertains to staff.

For Bird of Paradise pricing, scroll down for more information on packages and a discussion about how to get the best price…

Your Best Chance to Negotiate Price

Many villas will only take a 7 night booking. At Christmas/New Year’s, it’s not unusual for an Anguilla villa rental to require 10 to 14 day minimum. We have flexibility at the Bird of Paradise, but note that most guests come Saturday to Saturday, so if your vacation straddles a weekend (Thursday - Monday) and/or you only want an Anguilla villa rental for 3-5 days, the villa owner is going to most likely not be able to fill those other days of the week. They could lose two separate week bookings, because you want a long weekend.  Your chance of wheeling and dealing and negotiating a better price goes way down with less than 7 nights.

When you have more than 7 nights, your chances for negotiating a better price go up considerably with two weeks or even a month.

HINT: If you’re thinking of chef services, the same thinking applies. A chef wants a week-long booking. If you only want a single dinner, you’re going to pay a dear price as your reservation may cause him to lose work for an entire week at a villa.

What’s the budget you have in mind for an Anguilla villa rental? 

At the Bird of Paradise we adjust the services and amenities to fit our guests’ budget. In the luxury villa market in Anguilla, some villas, like the Bird of Paradise, include a lot of services and amenities in the published rate. If I know the budget, as the owner, I'm willing to reduce services or amenities to meet the guest's price expectations. They will still have a 5 star Anguilla villa rental, but maybe they want to cook their own breakfast to keep the price down. Maybe they don't need daily housekeeping or the welcome cocktail party. 

If I know the budget, I can make suggestions as to how we can achieve it. Don’t be coy. Come right out and tell us your budget, so we can tailor something especially for you. I’ve put together sample packages with look like this:

Sample options at Bird of Paradise Villa

  • Basic Package: No car and driver for arrival/departure. No chef or butler. No welcome cocktail party.

  • Silver Package: Car and driver for arrival and departure. Chef, food and beverage for welcome cocktail party. Chef and butler for one meal daily. We’re flexible. If you stay for a week, you’ll have 7 meals. Feel free to have 3 meals in one day and no meals on other days.

  • Gold Package: Silver package plus chef for daily breakfast, so two chef services daily.

  • Platinum Package: Silver package plus chef on-demand for whatever meal you want, or tapas, cocktail parties, etc.

Caribbean Villa Rentals with Chef

On Anguilla there are only 7 villas that indicate they have a chef on retainer. This will be the least expensive way for you to receive chef services. Otherwise... if you rent a villa that doesn't have a chef on retainer, expect to pay $300 to $450 for chef service for a lunch and $450 to $650 for a single dinner, depending on number of courses and guests. This does not include an additional $12 an hour for the server and does not include food and beverage. 

As mentioned above, beware of “breakfast included”. This is usually a housekeeper bringing store-bought rolls. Do you really want all those carbs every day? Our breakfasts are prepared by a chef and are eggs made to order, omelettes, fresh fruit, yogurt, fresh croissants, and whatever else you want!

If you rent one of the 7 villas with a chef, ask about your options. Do you pay for services you don’t use? If you want to go to one of the fun beach bars for lunch or enjoy fine dining on the island, are you still paying for that chef and server? If you're not using the full-time chef, do you get a discount or refund?

At the Bird of Paradise we offer a "no chef rate,” as you saw above, but if you have an interest in chef services, we are the only villa we know of with a chef in residence that offers options. You choose how many meals and only pay for what you use. Again, since our chef is on retainer, we can offer pricing considerably lower than quoted above.

Cost of Food and Beverage: 

Check out the fine print. Many villas will charge 10-20% service fee for purveying the food and beverage. At the Bird of Paradise, you only pay what's on the grocery receipts with no up-charge. This saves our guests hundreds of dollars.


We offer it, but we don't recommend it. It's in the guests' best interest to pay only for the food and beverage they order. All-inclusive rates are high because the owner has to assume the guests are eating and drinking lobster and champagne three times a day. 

Questions about Anguilla villa rentals? 

Feel free to email ( or call me on my cell (1.414.791.9461). Jon and I have visited Anguilla for 30+ years. We came as newlyweds, returned with a baby and have entertained teenagers and college students. I'm happy to help with answering your questions and help with the planning!