The Snowbird's Guide to Wintering on Points

Extended stays in Florida, Arizona, or the Caribbean don't have to drain your savings. Here's how to use points, loyalty perks, and a few lesser-known strategies to make your warm-weather escape more affordable than you think.

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Category: Educational (Lifestyle / Points Strategy)
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Meta Title: The Snowbird's Guide to Wintering on Points | WanderWise
Meta Description: Escape winter without draining your savings. How to use hotel loyalty points, credit card rewards, and extended-stay strategies for snowbird travel to Florida, Arizona, and the Caribbean.
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Every November, the same quiet migration begins. Millions of Americans start packing bags, forwarding mail, and pointing their cars — or their flights — toward warmer climates. Florida. Arizona. The Gulf Coast. The Caribbean. Wherever the thermostat doesn't require a parka.

If you're one of them, or you've been thinking about becoming one, you already know the biggest question isn't where — it's how much.

A winter away from the cold might sound like a luxury, but for many people in our audience, it's closer to a necessity. Cold weather isn't just uncomfortable after a certain point — it limits mobility, impacts health, and makes the simple act of getting out of the house feel like an expedition.

The problem is cost. A typical snowbird stay of two to four months can easily run $5,000 to $15,000 or more, depending on where you go and how you stay. That's a significant line item on any budget — especially a fixed one.

But here's what most snowbirds don't realize: the credit card points you've been accumulating through everyday spending can offset a meaningful portion of that cost. In some cases, a very large portion. It just requires a slightly different strategy than booking a three-night vacation.

The Snowbird Math: Why Points Work Differently for Long Stays

When most people think about using credit card points for travel, they picture booking a round-trip flight or a few nights at a hotel. Short stays. Quick redemptions.

Snowbird travel is a different animal. You're not booking five nights — you're booking five weeks. Or ten. Or sixteen. That changes the equation in ways that can work both for you and against you, depending on your approach.

Where points work beautifully for extended stays:

  • Flights. Whether you're flying one-way down in November and one-way back in April, or making a round trip, airline points and transferable credit card points can eliminate $400 to $1,200 in airfare per person.
  • The first week or two. Using hotel points to cover the opening stretch of your stay — while you settle in, explore neighborhoods, and finalize longer-term arrangements — is one of the smartest hybrid strategies available.
  • Breaks and side trips. A long winter in one place benefits from occasional variety. A weekend in Key West, a few nights in Sedona, a quick trip to the Bahamas — these short excursions are perfectly suited to point redemptions.

Where points require more thought:

  • Full-duration hotel stays. Booking 60 or 90 consecutive nights at a hotel entirely on points is technically possible but requires an enormous point balance. A more practical approach combines points with other strategies.

Let's walk through the options.

Strategy 1: Use Points for Flights, Save Cash for the Stay

This is the simplest approach and the one we recommend for most snowbirds who are new to points.

A one-way flight from a northern hub to Florida, Arizona, or the Caribbean typically costs $150 to $400 in cash. Two people, round trip, and you're looking at $600 to $1,600. That's real money — and it's exactly the kind of predictable expense that credit card points handle well.

If you have Chase Ultimate Rewards, American Express Membership Rewards, or Capital One miles, you can transfer those points to airline partners or book directly through your card's travel portal. A domestic one-way flight for 12,500 to 15,000 points is common through airline partners, or you can use the portal at a flat rate.

The result: your transportation to and from your winter home costs you points instead of cash, freeing up that cash for your actual stay.

For a refresher on how to book flights with points, our beginner's guide to credit card points covers the fundamentals.

Strategy 2: Points for the First Two Weeks, Then Transition

This is the strategy our WanderWise readers use most successfully.

The idea is straightforward: use hotel loyalty points to cover the first portion of your stay — typically 7 to 14 nights — while you settle into your snowbird destination and arrange longer-term accommodations. Monthly rentals, extended-stay apartments, and short-term leases all become easier to evaluate and negotiate once you're on the ground.

Here's how each major hotel program handles extended stays:

Marriott Bonvoy

Marriott operates the largest hotel network in the world, with roughly 8,800 properties. For snowbirds, the most relevant brands are:

  • Residence Inn by Marriott — studio and one-bedroom suites with full kitchens. Designed specifically for extended stays. Complimentary breakfast and evening socials at many locations.
  • TownePlace Suites — similar to Residence Inn, slightly more budget-friendly.
  • Marriott's branded residences and timeshare properties in Florida and Arizona.

Marriott points are worth approximately 0.7 to 0.9 cents each. A free night at a Residence Inn typically costs 20,000 to 35,000 points, depending on the market. Ten nights would require 200,000 to 350,000 points — a substantial balance, but achievable over time with strategic credit card spending.

The fifth-night-free benefit: Marriott offers a free fifth night on award stays of five consecutive nights. That means five nights for the price of four in points — an automatic 20% discount.

Hilton Honors

Hilton's extended-stay brands include:

  • Home2 Suites — modern, apartment-style suites with kitchens. Strong presence in Florida and Arizona.
  • Homewood Suites — spacious suites with full kitchens and complimentary evening receptions.
  • Embassy Suites — two-room suites with complimentary cooked-to-order breakfast.

Hilton points are worth approximately 0.5 to 0.6 cents each, meaning you need more of them — but Hilton also tends to be more generous with earning opportunities and credit card sign-up bonuses. A free night at a Homewood Suites might cost 30,000 to 50,000 points.

Hilton also offers a fifth-night-free benefit for award stays, identical to Marriott's.

Hyatt

Hyatt's extended-stay brand is Hyatt House, which offers suites with full kitchens, complimentary breakfast, and evening social hours. There are also Hyatt Place properties that work well for medium-term stays.

Hyatt points are worth considerably more — 2 to 2.5 cents each — so a free night at a Hyatt House for 8,000 to 15,000 points delivers excellent value. If you have Chase Ultimate Rewards points, the Chase-to-Hyatt transfer is one of the best moves available.

Hyatt's fifth-night-free benefit makes a five-night Hyatt House stay cost just 32,000 to 60,000 points — covering what might be $700 to $1,500 in cash. That's a strong opening salvo for your winter escape.

For a full comparison of these programs, our hotel loyalty program guide breaks down the strengths and weaknesses of each.

Strategy 3: The Monthly Rental Hybrid

Here's where snowbird travel gets genuinely strategic.

The most cost-effective approach for stays of 30 days or longer is typically a monthly rental — a furnished apartment, condo, or house booked through platforms like VRBO, Furnished Finder, Airbnb (for stays of 28+ days), or local property management companies.

Monthly rentals in popular snowbird destinations range from $1,500 to $4,000 per month, depending on the market and the property. That's often 40% to 60% less expensive per night than a hotel.

The points strategy here isn't about paying for the rental with points (most platforms don't accept them directly). Instead, it's about using your credit card strategically:

Earn points on the rental payment. A $2,500 monthly rental paid on a card that earns 2x or 3x points on travel (like the Chase Sapphire Preferred at 2x or the Capital One Venture at 2x) generates 5,000 to 7,500 transferable points per month. Over a four-month winter, that's 20,000 to 30,000 points earned — enough for several free hotel nights on your next trip.

Use points for the gaps. Monthly rentals often have minimum stays and fixed start dates. Points cover the nights before your rental begins, after it ends, or during any gaps if you're moving between properties.

Use points for side trips. One of the great pleasures of wintering somewhere warm is taking short trips from your base. Points are perfect for a weekend in the Caribbean, a few nights at a Gulf Coast resort, or a jaunt to a new city.

Strategy 4: The Credit Card Annual Fee Offset

Several premium travel credit cards include benefits that directly reduce snowbird costs:

Free night certificates. The Marriott Bonvoy Boundless card ($95 annual fee) includes a free night certificate each year for properties costing up to 35,000 points per night. The World of Hyatt card ($95 annual fee) includes a free night at Category 1–4 properties. The Hilton Honors American Express Surpass ($150 annual fee) includes a free night certificate after spending $15,000 in a year.

These certificates work beautifully for snowbird travel — use them at the beginning or end of your stay to extend your time without extending your budget.

Statement credits. Cards like the Chase Sapphire Reserve and the Amex Platinum include travel credits ($300 and $200, respectively) that can offset flight costs or certain travel purchases.

For more on how annual fees pay for themselves, our guide to credit card annual fees walks through the math in detail.

Best Snowbird Destinations by Points Value

Not all warm-weather destinations offer equal value on points. Here's where the math works best:

Florida

  • Fort Lauderdale / Miami area. Strong presence of all major hotel brands. Competition keeps award rates reasonable. Excellent for Hyatt House and Residence Inn extended stays.
  • Sarasota / Naples. Slightly more upscale, with fewer budget chain options — but beautiful and warm. Monthly rentals are the better play here for full-winter stays.
  • Tampa / Clearwater. Outstanding value. Lower cost of living than South Florida with similar weather. Good hotel point redemption options.

Arizona

  • Phoenix / Scottsdale. Abundant hotel options across all major brands. Winter is peak season, so cash rates are high — which actually makes points more valuable. A $350/night hotel that costs 15,000 points in January is a better deal than the same hotel for $150 and 15,000 points in July.
  • Tucson. More affordable than Scottsdale, with a calmer pace. Excellent monthly rental options.

The Caribbean

  • Cancún / Riviera Maya. The Hyatt Zilara and Hyatt Ziva all-inclusive resorts are some of the best point redemptions anywhere. For a two-week escape mid-winter, this is hard to beat.
  • Turks and Caicos. Premium destination with a strong Marriott presence (The Ritz-Carlton and a Marriott Autograph Collection property). Higher point costs, but extraordinary value compared to cash rates that frequently exceed $800 per night.
  • Puerto Rico. No passport required. Several strong hotel options in San Juan and along the coast. Monthly rentals in areas like Rincón offer remarkable value.

The Snowbird Points Calendar: When to Do What

Timing matters. Here's a month-by-month approach:

July–August (5–6 months before departure): Book award flights. Winter routes from northern cities to Florida, Arizona, and the Caribbean book up quickly on points. The earlier you search, the better availability you'll find.

September (3 months before): Book hotel award nights for your arrival window. Transfer points from Chase, Amex, or Capital One to hotel partners as needed. Confirm monthly rental arrangements.

October (1–2 months before): Use credit card sign-up bonuses earned throughout the year. Double-check all reservations. Consider booking a few strategic hotel nights for holiday periods (Thanksgiving, Christmas) when rental check-in/check-out dates may not align.

November–March (during your stay): Earn points on every purchase — groceries, dining, gas, utilities. Every dollar you spend in your winter location is a dollar that can earn points toward next year's escape. Use a card that earns at least 2x on the categories you spend most in.

April (return): Book your return flight on points if you haven't already. Evaluate the past season: what worked, what didn't, and how many points you have for next year.

Common Questions

Can I really save thousands of dollars as a snowbird using points?

Yes — but the savings come from multiple smaller wins rather than one big redemption. Flights on points ($600–$1,600 saved), two weeks of hotel on points ($1,500–$3,000 saved), free night certificates ($200–$500 saved), and points earned on winter spending (building your balance for next year). Combined, it's realistic to offset $3,000 to $6,000 of annual snowbird costs through a thoughtful points strategy.

What if I've never used points before?

Start simple. Our beginner's guide walks you through everything from zero. The most important first step is knowing what you already have. Our Travel Score Quiz can help you take stock in about 60 seconds.

I rent the same place every winter. Can points still help?

Absolutely. Even if your primary accommodation is a monthly rental, points cover flights, side trips, hotel stays during transition periods, and dining rewards throughout your stay. And by putting your rental payment on a rewards credit card, you're building your points balance for the following year.

The Bottom Line

Wintering somewhere warm isn't a luxury reserved for people with unlimited budgets. It's a practical decision that millions of Americans make every year — and credit card points can make it meaningfully more affordable.

You don't need a million points or a complex strategy. You need a plan: use points for flights, cover your arrival period with hotel awards, transition to a cost-effective monthly rental, and earn points on everything you spend while you're there. Repeat annually, and the system gets stronger each year.

The cold isn't going anywhere. But with the right approach, you don't have to be there for it.

Not sure which cards or points programs fit your snowbird plans? Take our Travel Score Quiz — it takes about 60 seconds and gives you a personalized starting point.

WanderWise helps adults 55+ travel smarter using credit card points and travel rewards. Our recommendations are based on independent research. If you apply for a credit card through one of our links, WanderWise may receive a referral commission — but our recommendations are never influenced by compensation. Read our full editorial policy.