Luxury Villas for Presidents’ Day 2027: Where to Go and When to Book
Presidents’ Day 2027 falls on Monday, February 15, and in New York and many other school districts the whole week is off. For that week, the warm choices are the Caribbean, from Turks and Caicos, St Barts and Anguilla to Barbados and the Dominican Republic, and Mexico’s Pacific coast in Los Cabos and Punta Mita; for families who ski, the Alps. Below are 23 houses from our collection for the week, what each one includes, and when to book: for the Caribbean and Mexico, that means October. The island houses are part of our Caribbean villa rentals.
Presidents’ Day 2027: the dates that matter
- The holiday: Monday, February 15, 2027. The long weekend runs Saturday 13 to Monday 15, and Valentine’s Day falls on the Sunday.
- The school week: New York City public schools are closed for midwinter recess from Monday, February 15 to Friday, February 19, and many districts in the Northeast take the same week.
- Canada: the same Monday is Family Day in Ontario, Alberta, British Columbia, Saskatchewan and New Brunswick, and a provincial holiday under other names in Manitoba, Nova Scotia and Prince Edward Island.
- England: most schools take their February half-term from February 15 to 19, so British families are looking at the same week, above all for ski chalets.
- The ski resorts: the Ikon Base Pass is blacked out on February 13 and 14, 2027, a sign of how full the mountains are that weekend.
- The week that covers it all: Saturday, February 13 to Saturday, February 20 takes in the long weekend, Valentine’s Day and the school week.
Why Presidents’ Day week books before Christmas
Three calendars land on the same seven nights. American, Canadian and British families are free in the same week, and the families who travel with grandparents and children ask for the same thing: one house, enough bedrooms, and staff to run it. There are only so many of those houses on each island.
Luxury travelers are booking further ahead. At its Travel Week in Las Vegas in August 2026, Virtuoso, the luxury travel network, reported that 42 percent of its advisers see clients booking further ahead to secure their preferred options, that multigenerational and family travel led the trips clients are asking for more of, cited by 69 percent, and that sales for trips one and two years out were up 50 percent on a year earlier.
Most people start looking in January. In the US search data we track, searches for St Barts villa rentals more than triple between September and January, and searches for Turks and Caicos villas peak in January. By the time most families search for February, the largest houses, and those with a full staff, are usually the first ones gone.
How we plan the winter
We work through the winter in order. In September, the February dates and the last Christmas and New Year villas; in October, Presidents’ Day week and spring break; in November, what is left. If you are reading this in October, you are on time for Presidents’ Day: the houses below can still be compared side by side, and the choice is yours rather than whatever remains.
Our advice: hold the house first, then book the flights around it.
Where to go for Presidents’ Day, at a glance
| Destination | From New York | Best for |
|---|---|---|
| Turks and Caicos | Nonstop to Providenciales, about 3 hr 45 min | The shortest flight to the Caribbean; large beachfront houses on Grace Bay |
| St Barts | Nonstop to St Maarten, then a short flight or ferry | Restaurants, beach clubs and a French harbor town |
| Anguilla | Nonstop to St Maarten, then a short boat crossing | Quiet beaches and fully staffed estates for 20 |
| Barbados | Nonstop to Bridgetown | Sandy Lane, golf and houses with a cook and a butler |
| Dominican Republic | Nonstop to Punta Cana | Gated resorts with golf, and private resorts for 20 to 28 |
| Los Cabos | Nonstop to San José del Cabo | Whale season on the Pacific and beachfront houses in Palmilla |
| Punta Mita | Nonstop to Puerto Vallarta, then about an hour by road | A gated peninsula with beach clubs and golf |
| The Alps | Overnight nonstop to Geneva or Zurich, then by road or rail | Ski weeks in a catered chalet |
| Miami | About 3 hr nonstop | The long weekend on its own |
Scheduled nonstops change with the season; we confirm the current flight when we plan your week. For more on the shortest hops, see our guide to short flights from NYC to the beach.
Turks and Caicos
The shortest nonstop from New York to the Caribbean, and second in our Billionaire Villa Index 2026. February is the dry season, and Grace Bay is where the large beachfront houses are. See all our Turks and Caicos villas.
Villa Hawksbill
Grace Bay, Providenciales · 11 bedrooms · sleeps 22
An eight-bedroom main villa and the three-bedroom Beach House, set directly on Grace Bay, with a tennis court, a gym, a heated pool and a private dock. It can be taken with six, eight or all eleven bedrooms, so it suits anything from one family to three generations together.
Staff and service: fully staffed, with a private chef and butler service.
Villa Awa
Grace Bay, Providenciales · 6 bedrooms
A modern beachfront house entered by a bridge over a reflecting pool, with a heated infinity pool facing the bay. For a larger group it can be rented with neighboring Villa Sentosa, for up to 28 guests between the two.
Staff and service: a private chef, a butler and a pool attendant are included.
Villa Kailoa
Long Bay Beach, Providenciales · 4 bedrooms
A two-story house above Long Bay, with an infinity lap pool that has a shallow area for small children, a hot tub and a tennis court. The right size for one family, about nine miles from the airport.
Staff and service: daily housekeeping and an evening security guard are included.
Dream Estate at Ambergris Cay
Ambergris Cay, a private island · 11 bedrooms
Two connected villas, two oceanfront bungalows and two courtyard cottages, with four heated pools, on a private island at the quiet end of the archipelago. Everything beyond the gate is included: meals in the island’s restaurants, drinks, the spa, the watersports, golf carts and the transfers, twenty minutes by air from Providenciales or ten minutes from South Caicos.
Staff and service: fully staffed and all-inclusive.
St Barts
February is high season on the island. Fly to St Maarten, then take the short hop by air or the ferry. See all our St Barts villa rentals.
Villa Lagon Vert
Petit Cul-de-Sac · 7 bedrooms
A recently built single-level house in the Domaine du Levant, with two pools, one on the front terrace facing the ocean and one in the garden, and an air-conditioned TV room for the children’s movie nights.
Villa Antares
Mont Jean · 5 bedrooms · sleeps 10
Five suites, two of them facing the sea, around a heated infinity pool. It can also be taken with three or four bedrooms for a smaller family.
Staff and service: daily housekeeping, with a private chef on request.
Villa Lao
Above Corossol · 3 bedrooms · sleeps 6
Three bedrooms on three floors, each with its own terrace, a heated infinity pool facing the sunset, a gym and a jacuzzi. Gustavia is five to seven minutes by car and the airport fifteen to twenty. Seven-night minimum, which fits the school week exactly.
Anguilla
Quieter than St Barts, with long, empty beaches and some of the largest staffed estates in the Caribbean. Fly to St Maarten, then cross by boat. See all our Anguilla villas.
Villa Le Bleu
Little Harbour · 11 bedrooms · sleeps 20
Lawns run down to two private beaches. There are two pools, a floodlit tennis court, a private cinema and a games room, and the two Garden Suites across the lawn have their own pool: families give them to the older children.
Staff and service: a full staff, including a private chef.
ÀNI Anguilla
Little Bay, on the north shore · 10 bedrooms · sleeps 20
A private resort on a clifftop above Little Bay, taken by one group at a time: two villas, each with its own pool, hot tubs, a gym and a tennis court, four minutes on foot from the beach.
Staff and service: fully staffed, with a private chef.
Kishti West
Meads Bay · 5 bedrooms
Directly on Meads Bay, a mile of beach with restaurants and beach cafes within walking distance. A heated infinity pool, a beachside hot tub, a home theater and two kitchens.
Staff and service: a private chef and a property manager.
Barbados
A nonstop from New York to Bridgetown, and February is in the dry season. See all our Barbados villas.
Casablanca
Sandy Lane area, St James · 7 bedrooms
Set in wide grounds overlooking the Sandy Lane golf course, with an infinity-edge pool, a gazebo for dinner outdoors and its own tennis and pickleball court.
Staff and service: a cook, a butler, housekeepers and a laundress.
Jamoon Sandy Lane
Sandy Lane Estate, St James · 7 bedrooms · sleeps 14
Inside Sandy Lane Estate, with two master suites on private terraces, a piano room, a tennis court and covered terraces for long lunches.
Staff and service: a chef, a butler, a housekeeper and a laundress, with a welcome basket on arrival.
Dominican Republic
A nonstop to Punta Cana, gated resorts with golf for families who like a little structure, and on the north coast, private resorts for the whole extended family. See our Punta Cana villas and all our Dominican Republic villas.
Ananda
Punta Cana Resort · 8 bedrooms · sleeps 16
Inside the gated Punta Cana Resort, under three miles from the airport, with golf on site, a large pool and an outdoor kitchen for barbecues. Children are welcome. Three-night minimum.
Staff and service: fully staffed, with a private chef and butler service.
Corales 114
Corales, Puntacana Resort & Club · 6 bedrooms · sleeps 14
Three pavilions around a French-style courtyard on the Corales championship golf course, with a pool on the lower terrace and galleries that look over the fairways.
Staff and service: a full staff, with a private chef and butler service.
ÀNI Dominican Republic
Rio San Juan, on the north coast · 14 bedrooms · sleeps 28
An all-inclusive private resort on its own peninsula, for one group at a time, with two villas facing infinity pools, a water slide and a tennis court, and direct access to the bay known as La Piscina Natural.
Staff and service: fully staffed and all-inclusive.
Los Cabos
On the Pacific side, February is whale season: humpback whales pass the coast from December to April. Fly nonstop to San José del Cabo. See all our Los Cabos villas.
Villas Del Mar 461
Palmilla, on the beach · 5 bedrooms · sleeps 10
Directly on the sand in the gated Villas del Mar community, facing the Sea of Cortez, with a pool, a hot tub and a gym.
Staff and service: a personal butler and a private chef for breakfast and lunch, daily housekeeping and a dedicated concierge.
Casa Roca De Pajaro
Caleta Palmilla · 5 bedrooms · sleeps 10
Four ocean-view suites in the main house and a separate casita for grandparents, older teenagers or another couple, with direct access to a private beach and a heated pool.
Punta Mita
A gated peninsula on the Pacific north of Puerto Vallarta, with beach clubs, golf and villas where the staff and the meal plan come with the house. See all our Punta Mita villas.
Casa Palmasola
Punta Mita, on the beach · 9 bedrooms · sleeps 22 with children
A beachfront compound with a 200-foot pool, a gym, a massage room and a family room for movies and foosball. It sleeps up to 18 adults, or 22 guests with children.
Staff and service: a full-time staff of seventeen and a complete meal plan, with the food and drinks included.
Estate la Sierra
Kupuri, Punta Mita · 5 bedrooms
Inside the gates of Punta Mita, with a courtyard and water feature, a fire pit and a pool, and a golf membership that includes the Punta Mita beach clubs.
Staff and service: a chef for breakfast and lunch (the food is extra), daily housekeeping and a house manager.
The Alps: the ski week
For a family that skis, this is the most contested week of the winter, because the British half-term falls on the same dates. Catered chalets for this week are best booked twelve months ahead. See our Swiss Alps chalets and Courchevel chalets.
Chalet Zermatt Peak
Zermatt · 5 suites · up to 10 adults and 3 children
A four- to five-minute walk from the village, with a spa of its own: Finnish and Swedish saunas, a hammam, a jacuzzi and treatments by ESPA.
Staff and service: fully staffed and fully catered, with a private chef and an open bar.
Chalet La Vigne
Verbier · 4 bedrooms · sleeps 8
Above Verbier in the Patier area, facing south-east, with an indoor pool, a hammam, a gym, a cinema and an outdoor hot tub on the terrace.
Staff and service: chalet staff and a private chef.
Chalet Courchevel
Courchevel 1850 · 7 bedrooms · sleeps 14
In the Nogentil district, 50 meters from the Bellecôte piste, with five levels joined by an elevator and a spa with a heated pool, a hammam and a gym.
Staff and service: a private chef and butler service.
Miami: the long weekend
About three hours from New York, and the only place on this list that works for the long weekend alone. See all our Miami villa rentals.
Venetian Star
Venetian Islands, Miami Beach · 5 bedrooms
Bay views from the east end of Venetian Island, with a pool and a dock; Lincoln Road and the beach are within walking distance. Two-night minimum.
Staff and service: 24/7 concierge service.
Booking the week: what to settle first
- The nights. Saturday, February 13 to Saturday, February 20 covers the long weekend, Valentine’s Day and the school week. Shorter stays are possible where the minimum allows.
- The minimum stay. It varies by house: on their listings, Villa Lao asks for seven nights, Ananda three and Venetian Star two, and owners can set longer minimums for holiday weeks. We confirm it in writing before you book.
- Which meals the staff cover. “Chef included” can mean breakfast and lunch, as at Villas Del Mar 461 and Estate la Sierra, or every meal with the food included, as at Casa Palmasola and Chalet Zermatt Peak. Ask which meals, and whether the food is in the rate.
- Valentine’s Day. It falls on the Sunday. Our concierge books the table, or arranges a private dinner at the villa.
- Flights and transfers. Hold the house first, then the nonstop; the concierge arranges the transfer from the airport.
After Presidents’ Day: spring break and Easter 2027
Easter Sunday 2027 falls on March 28, the earliest since 2016, so many spring breaks and Easter weeks will fall in March; New York City public schools’ spring recess runs from April 22 to 30. The same houses serve both, and in our calendar they are placed in October too. For March, see the best Caribbean islands to visit in March.
Frequently asked questions
When is Presidents’ Day 2027?
Monday, February 15, 2027. Valentine’s Day falls the day before, on Sunday the 14th, and New York City public schools are closed all week for midwinter recess, from February 15 to 19.
Where is warm for Presidents’ Day weekend?
The Caribbean and Mexico are in their dry season in February: Turks and Caicos, St Barts, Anguilla, Barbados, Punta Cana, Los Cabos and Punta Mita. From New York, Miami is about three hours and Turks and Caicos about three hours and forty-five minutes nonstop.
How far ahead should we book a villa for Presidents’ Day week?
Four to six months ahead is the usual window for the Caribbean and Mexico in high season, so October is the month to book, and the largest houses go earlier. For a ski chalet that week, plan twelve months ahead.
Is February hurricane season in the Caribbean?
No. The Atlantic hurricane season runs from June 1 to November 30, and February is in the dry season across the Caribbean.
Is Presidents’ Day week busy in the Alps?
Yes. It is also the February half-term in most of England and Family Day in much of Canada, and in the US the Ikon Base Pass is blacked out on February 13 and 14, 2027. Book a catered chalet for that week twelve months ahead.
Which villas suit a large family group for Presidents’ Day?
Villa Hawksbill in Turks and Caicos sleeps 22, Casa Palmasola in Punta Mita 22 with children, ÀNI Dominican Republic 28, and Villa Le Bleu and ÀNI Anguilla 20 each.
Do villas have a minimum stay for Presidents’ Day week?
It depends on the house. On their listings, Villa Lao asks for seven nights, Ananda three and Venetian Star two, and owners can set longer minimums for holiday weeks. We confirm the minimum in writing before you book.
How much does a villa cost for Presidents’ Day week?
It depends on the house, the size of the group and how much staff and food you want included. We quote the villas open for your dates, with what is included set out in writing.
Hold your Presidents’ Day week
Tell us your dates, your group and the kind of week you want. A specialist replies within 24 hours with a private shortlist of villas open for February 13 to 20, with the staff and the minimum stay confirmed in writing.
Request a Tailored SelectionWhatsApp +1 305 432 1731
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