Flamands · St. Barts
Villa Wake Up
- Listed as beachfront
- Heated pool
- Hot tub
- Sleeps
- 12
- Bedrooms
- 6
- Baths
- 6
Butler · housekeeper · chef on the listing
$237,455$33,922 / night
7 nights, Feb 6 to 13, 2027, fees and taxes included
Luxury Caribbean villa rentals
Five destinations for US travelers, compared by flights and entry rules. Each listing names the company you book with.
5 destinations608 homesfrom $6,634 · 7 nights, May 8 to 15, 2027
Caribbean villas
Showing 6 of 608 homes
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Leeward Settlement · Turks and Caicos
Sole e Mare
- Listed as beachfront
- Infinity pool
- Hot tub
- Sleeps
- 20
- Bedrooms
- 10
- Baths
- 10.5
Staff on site
$452,620$64,660 / night
7 nights, Feb 6 to 13, 2027, fees and taxes included
Treasure Beach · Jamaica
Out of the Blue on the Beach
- Listed as beachfront
- Private pool
- Sleeps
- 8
- Bedrooms
- 4
- Baths
- 4
Staff on site
$6,634$948 / night
7 nights, May 8 to 15, 2027, fees and taxes included
Mullins Bay · Barbados
The Great House
- Listed as beachfront
- Infinity pool
- Gym
- Sleeps
- 30
- Bedrooms
- 12
- Baths
- 12
Staff on site
$185,640$26,520 / night
7 nights, Mar 13 to 20, 2027, fees and taxes included
Totals are the company’s quote, with the fees and taxes it lists.
Long Bay Village · Anguilla
Nevaeh
- Listed as beachfront
- Infinity pool
- Hot tub
- Sleeps
- 20
- Bedrooms
- 9
- Baths
- 8
Staff on site
$119,249$17,036 / night
7 nights, Mar 13 to 20, 2027, fees and taxes included
Totals are the company’s quote, with the fees and taxes it lists.
St Jean · St. Barts
Villa BDM
- Listed as beachfront
- Infinity pool
- Sea view
- Sleeps
- 18
- Bedrooms
- 7
- Baths
- 7
$207,006$29,572 / night
7 nights, May 8 to 15, 2027, fees and taxes included
Home photos: Top Villas
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Caribbean villa destinations
Caribbean
St. Barts
French Caribbean island with a runway of about 2,100 ft (650 m). Dry season December to May.
Caribbean
Turks and Caicos
British Overseas Territory of eight main islands, with nonstop flights from at least nine US cities and a 9,200 ft (2,800 m) runway on Providenciales.
Caribbean
Jamaica
Half of Jamaica’s villa guests stayed around Montego Bay in 2024, a short drive from Sangster International Airport.
Caribbean
Barbados
Island of 166 square miles (430 km²) with calm Caribbean water on the west coast and Atlantic surf on the east.
Caribbean
Anguilla
Homes around Long Bay Village and The Valley.
Compare Caribbean destinations
| Destination | From the US | US passport | Driving | Tax on the rent |
|---|---|---|---|---|
| St. Barts | Connect through St. Maarten, San Juan or Antigua, then small plane or ferry | Needed, valid for more than six months on arrival | Right | 5% |
| Turks and Caicos | Nonstop to Providenciales from at least nine US cities | Needed; six months’ validity covers both official rules | Left | 12% |
| Jamaica | American, Delta, JetBlue, Southwest and United fly to Montego Bay | Needed, valid on entry and exit, plus the online C5 form | Left | US$1 per room per night. GCT of 10% on tourism services, due to cover short-term rentals from April 1, 2027 |
| Barbados | Daily nonstops from New York and Miami | Needed, valid for the whole trip | Left | 10% Shared Economy Levy on short-term rentals |
Each total on Gladori is the company’s quote, with the fees and taxes it lists. Rules checked November 5, 2026; flights change by season.
Services in the Caribbean
Arranged by the company named on your listing or by independent providers on each island.
- Concierge in the CaribbeanRestaurant tables and a car waiting at the airport.Quotes per request
- Household staff in the CaribbeanDaily housekeeping and nannies.Quotes per night
- Private chef in the CaribbeanSome dinners or every meal.Quotes per request
- Yacht charter in the CaribbeanBoats by the day or the week.Quotes per request
- Charter flights in the CaribbeanSmall planes between the islands.Quotes per flight
- Private jet charter to the CaribbeanFrom US airports to the runway nearest the house.Quotes per route
Ask about a service
Services are provided by independent companies, which may pay Gladori a commission. How we’re paid
Why book through Gladori
Why book a Caribbean villa through Gladori
You book with the company named on the listing, at the price it sets. Each listing shows that company, what’s included and when the price was checked.
Who you book with
Each listing names the company you book with and where you sign the booking.
What’s included
Each listing separates what’s included from what you can request, and what you pay for separately.
Prices with a date
Rates are the company’s published prices, shown with the date they were checked.
How we’re paid
The company you book with pays us a commission when you book through our links, and some companies pay us for requests sent from this site. It’s stated next to every button and form.
Caribbean villa rentals: questions
What does a Caribbean villa cost?
Each total is the company’s quote, with the fees and taxes it lists. Optional staff and extras are on top, and each listing shows them.
Are Caribbean villas on the beach?
Some are. On Gladori, a beachfront villa has sand at the end of its garden, with no public road in between.
Do Caribbean villas have private pools?
Each listing says so. Use the Private pool filter to see the ones that do.
Can I rent a Caribbean villa directly from the owner?
On Gladori you book with the company named on the listing. It may manage the house itself or list it for the owner.
When is the best time to rent a villa in the Caribbean?
Most of these destinations are driest from about December to April. The Atlantic hurricane season runs June 1 to November 30, and each destination page has its own months.
Shortlist
Tell us about your Caribbean trip
We send your request to the companies with matching homes. You get their options by email and book with the company you choose.
- You send dates, group size and what matters most.
- The companies reply with available homes and prices.
- You book with the company you choose.