Long Stays
Long Stay Escapes for Canadian Snowbirds
When the temperatures drop, many Canadians head south in search of sunshine, relaxation, and a slower pace of life. Our Long Stay options are designed with Snowbirds in mind—offering links to learn more about extended getaways to warm, welcoming destinations with all the comforts of home. Whether you’re looking to settle in for a month or an entire season, discover affordable accommodations, rich local culture, and the peace of mind that comes with thoughtfully planned travel.
For information on entry requirements for longer stays, banking information, currency, driver’s licenses, weather, phone and internet companies, where to buy groceries and even medical information, please check each country’s own page (click on their logo below), then look under the Quick Facts section as well as the Travel Essentials section at the bottom of each destination page.
Shoal Bay Villas
Length of Stay: 30 day room rate; on a month-to-month basis
For questions and reservations, please email for details: Send Email to Shoal Bay
There are a range of properties that are appropriate for longer stays, and these can be booked through platforms such as AirBnB and Vrbo.
How to Make Payments: Credit and debit cards are widely accepted thorough platforms like Airbnb, Vrbo, and Booking.com. Online payment platforms such as PayPal, and Stripe are commonly used for direct bookings, offering secure transactions and are user-friendly for international guests. Long-term bookings may require bank or wire transfers. Cheques and money orders are accepted by some rental companies but less common.
Link to Antigua and Barbuda’s website for longer stay properties: Learn More
There are a range of properties that are appropriate for longer stays.
How to Make Payments: Deposits and final payments are usually made through credit cards.
Link to Aruba’s website for longer stay properties: Learn More
There are a range of properties that are appropriate for longer stays in Barbados
Room Categories: Guest Houses & Apartments, Intimate Hotels and Villas
How to Make Payments: Credit and debit cards are widely accepted through platforms like AirBnB and Booking.com. Long-term bookings may require bank or wire transfers. Security deposits may be required.
Learn More: Guest Houses & Apartments | Intimate Hotels | Villas
There are a range of properties that are appropriate for longer stays in Bonaire.
Companies to contact for long stays: Sunbelt Realty; Caribbean Homes Bonaire; Remax; Bonaire Realty; Harbourtown Real Estate; SunRentals Bonaire; Sunwise
There are a range of properties that are appropriate for longer stays in the British Virgin Islands.
Companies to contact for long stays: Villa Virgin Gorda; BVI Luxury Villas; Columbus Sunset Vacation Apartments; Virgin Gorda Villa Rentals, and St. Bernard’s Hill House.
Long Bay Beach Resort welcomes extended Caribbean stays of 28 nights or longer between October and May (on request), subject to availability and seasonal blackout periods. Spacious beachfront villas and suites, high-speed Wi-Fi, wellness facilities, dining, watersports and the relaxed pace of Tortola make Long Bay an appealing winter alternative for Canadian travellers seeking an extended stay in the Caribbean.
There are a range of properties that are appropriate for longer stays.
Room Categories: Apartments, Condos, Villas, and Guesthouses.
How to Make Payments: Credit and debit cards are widely accepted. Long-term bookings may require bank or wire transfers. Cheques and money orders are accepted by some rental companies but less common. For long-term rentals, you’ll need to pay a security deposit, usually the equivalent of one month’s rent. Like in other places, this is refundable at the end of your lease, provided there are no damages or outstanding bills. We always recommend checking and documenting the property’s condition when you move in and out.
Link for more information on Where To Stay/Long Term Rentals
There are a range of properties that are appropriate for longer stays.
Room Categories: Guesthouses, Vacation Rental Properties
How to Make Payments: Credit and debit cards are widely accepted thorough platforms like Airbnb, Vrbo, and booking.com. Online payment platforms such as PayPal, and Stripe are commonly used for direct bookings, offering secure transactions and user-friendly for international guests. Long-term bookings may require bank or wire transfers . Cheques and money orders are accepted by some rental companies but less common.
Link for more information on Guesthouses | Vacation Rentals
There are a range of properties that are appropriate for longer stays.
Room Categories: Apartments, Guesthouses, Villas
How to Make Payments: Credit and debit cards are widely accepted. Long-term bookings may require bank or wire transfers. Security deposits may be required.
Link for more information on Apartments | Guest Houses | Villas
La Créole Beach Hôtel & Spa AND Mahogany Hôtel Residence & Spa offer special rates for guests staying 28 nights or more.
Black out dates: From December 22, 2026 to January 2, 2027 and from February 1 to 8, 2027
Room Categories: Apartments, Hotels
How to Make Payments: Credit and debit cards are widely accepted. Long-term bookings may require bank or wire transfers. Security deposits may be required.
For more information: Send an email to Cassandre: info@deshotelsetdesiles.com
Jamaica Inn – Snowbird Extended Stay – Stays of 28 Nights or More
Ideal for remote workers, retirees, or those ready to fully embrace island life.
- 5 Nights Free, when staying 28 consecutive nights
- 10% off all Food & Beverage and Gift Shop purchases
- 20% off Spa Treatments plus 2 free massages
- Continental Breakfast; Daily Delights; Bespoke Activities
- Travel Period: November 1, 2026 – May 31, 2027
- Booking Window: October 1, 2026 – April 30, 2027
For more information: Email Elaine Carnegie, The Canlink Collection or Call 905-235-9091
There are a range of cozy accommodations in Montserrat that are well-suited for longer stays.
Room Categories: Apartments, Villas
How to Make Payments: Most apartment and villa rentals accept bank or wire transfers, credit and debit cards, and many work through online platforms such as Airbnb and VRBO. These platforms offer secure, user-friendly booking options ideal for international guests. All villas are well equipped and are surrounded by mountain and sea views.
How to Book: Please contact our local real estate agents who are responsible for booking rental properties. Click here for a list of Vacation Rentals
The best recommendation for Canadian Snowbirds or digital nomads is to book a local Air BnB for long term stays. If you are looking for a long-term stay hotel, we recommend La Santa Maria Resort in San Juan del Sur.
How to Make Payments: Most apartment and villa rentals accept bank or wire transfers, credit and debit cards, and many work through online platforms such as Airbnb and VRBO. These platforms offer secure, user-friendly booking options ideal for international guests. All villas are well equipped and are surrounded by mountain and sea views.
Golden Rock Resort
Make Golden Rock Resort your home base for an extended Caribbean escape. Our One-Bedroom Cottages and Villas come equipped with full kitchen facilities, offering guests the flexibility of self-catering — ideal for longer stays. St. Eustatius’ central location makes it easy to explore neighbouring islands on day trips, then return each evening to the peace and tranquility that only Golden Rock Resort provides. For guests planning an extended visit, contact us directly for customised long-stay offers tailored to your travel plans.
Length of Stay: 30 day room rates available; on a month-to-month basis
For questions and reservations, please email for details: Send Email to Golden Rock