Where to Buy a Vacation Rental in 2026: Cross-Referencing The Points Guy’s Picks with Local Market Data

Hook: Your listing is invisible. Here's how to make it the destination people actually book in 2026.

Short-term rental listings pile up in every marketplace. You know the pain: great photos, weak inquiries; a listing that never hits consistent occupancy; or a viral travel story that doesn’t translate into bookings. In 2026 the solution isn’t just “pick a hotspot.” It’s combining travel momentum—what travelers actually want this year—with hard local market data to find vacation rentals that deliver repeat demand and sustainable returns.

Topline: What this guide gives you

Cross-referencing The Points Guy’s 2026 travel hotlist with short-term rental metrics, this guide gives investors and agents:

• 7 actionable vacation-rental investment picks for 2026 (travel momentum + market metrics).
• Sample cap-rate math and seasonality notes so you can run quick triage on deals.
• A repeatable checklist to cross-reference travel coverage with local STR data sources (AirDNA, county TOT, property managers).
• Advanced 2026 strategies — regulatory, distribution, and marketing plays — to turn listings into market-leading revenue engines.

Why this matters in 2026

Late 2025–early 2026 travel trends show two big forces shaping profitable vacation rentals:

• Experience-first travel: Travelers prioritize unique stays and off-peak experiences after years of mass-market travel rebound. That drives demand to secondary markets and curated niche stays (eco-lodges, work-friendly retreats).
• Regulation and platform shifts: Cities continue to refine STR rules; platforms emphasize verification and longer stays, and commission structures are evolving. That increases the value of compliant, professionally managed listings.

Method: How we cross-reference TPG picks with market data

High-level travel buzz is a lead generator — not a buy signal by itself. Use this 5-step framework (applied to The Points Guy’s travel hotlist) before bidding:

1. Identify the travel momentum — Is the destination getting pushed as a 2026 must-visit by mainstream travel outlets? That indicates elevated demand for at least one to three seasons.
2. Pull STR metrics from AirDNA, Transparent/STR, or local property managers: Occupancy, ADR (average daily rate), RevPAR, and seasonal occupancy curve.
3. Check local receipts & regulation — TOT (transient occupancy tax) revenues, short-term rental permit counts, and recent city council actions. Rapid TOT growth + permissive rules = upside; frequent clampdowns = risk premium.
4. Estimate expenses and financing — Insurance, utilities, HOA, vacancy buffer, and realistic mortgage assumptions in 2026. Use conservative occupancy in off-seasons.
5. Calculate cap rate and cash flow scenarios — Run three cases: conservative, baseline, and upside (e.g., post-marketing or renovation uplift).

7 Vacation-Rental Investment Picks for 2026 (TPG-aligned + market-ready)

Below are curated picks where travel-hotlist momentum (early 2026 travel press) intersects with STR metrics that can produce attractive returns if you do the homework. Each has sample cap-rate estimates, seasonality, and risk notes.

1) Coastal Algarve / Lisbon Coast, Portugal — Urban + Coastal Combo

• Why now: Portugal continues to top European travel lists in 2026 for safe, experiential travel and easy intra-Europe access—perfect for short stays and shoulder-season demand.
• Property type: 1–2 bed apartments in Lisbon; 2–3 bed villas near the Algarve towns.
• Seasonality: Peak Apr–Oct; shoulder seasons Mar & Nov drive European weekenders.
• Sample metrics: ADR €160–€280; occupancy 55%–70% (annual).
• Sample cap-rate: 4.5%–7% (NOI after operating expenses). Example: ADR €200 x 0.62 occupancy = €45,260 annual revenue; 40% operating expense = €27,156 NOI; purchase price €450,000 => 6.0% cap.
• Risk: Local licensing and tourist tax compliance required; buy in neighborhoods with strong transport links for year-round demand.

2) Baja California Sur (Cabo & La Paz corridor), Mexico — Beach demand + rising luxury bookings

• Why now: Mexico remained a resilient travel winner in 2025 and early 2026. American and Canadian travelers are returning for beachfront villas and wellness retreats.
• Property type: Small villas, condo developments with resort facilities.
• Seasonality: Peak Nov–Mar (winter sun); shoulder Apr & Oct.
• Sample metrics: ADR $275–$600; occupancy 45%–65%.
• Sample cap-rate: 4%–6.5% for beachfront luxury; 6.5%–9% inland. Example: ADR $350 x 0.55 occupancy = $70,388 revenue; 45% expenses = $38,713 NOI; price $650,000 => 6.0% cap.
• Risk: Title diligence, foreign ownership structure, and management reliability. Use a reputable local manager and validate TOT compliance.

3) Mountain Resort Town (U.S.) — Think Bend, OR / Western resort markets

• Why now: The experience economy and remote work continue to boost longer winter and shoulder stays at mountain destinations.
• Property type: 2–4 bed cabins, turnkey condos close to trails/lifts.
• Seasonality: Winter peak (Dec–Mar) and summer peak (Jun–Aug) for outdoor towns; shoulder demand remains strong due to remote workers.
• Sample metrics: ADR $225–$475; occupancy 50%–75% (higher in dual-season towns).
• Sample cap-rate: 5%–9%. Example: ADR $300 x 0.65 occupancy = $71,175 revenue; 38% expenses = $44,188 NOI; price $525,000 => 8.4% cap.
• Risk: Short-term rental regulations in some mountain towns tighten quickly; check city ordinances and HOA rules before bidding.

4) Portuguese Islands & Eco-destinations (Azores / Madeira) — Off-grid + year-round niche

• Why now: Travelers seek nature-based, low-density escapes in 2026; islands with improved air links are seeing sustained growth.
• Property type: Small guesthouses, duplexes, converted farm stays.
• Seasonality: Peak Apr–Oct but with steadier year-round tourism than mainland rural spots.
• Sample metrics: ADR €120–€240; occupancy 45%–68%.
• Sample cap-rate: 5%–8% depending on tourism infrastructure and owner involvement.
• Risk: Management logistics and higher delivery costs; strong partnerships with local operators reduce friction.

5) Colonial & Cultural Cities in Latin America (e.g., Oaxaca, Cartagena) — Experiential travel hotspots

• Why now: Food, culture, and UNESCO sites remain powerful magnets post-2025. Longer stays for cultural immersion are a rising trend.
• Property type: Restored colonial homes, boutique apartments.
• Seasonality: Peak Dry Season (Dec–Apr); off-peak rainy months still draw lower-volume long-stay bookings.
• Sample metrics: ADR $95–$250; occupancy 50%–72%.
• Sample cap-rate: 6%–10% if purchase price is favorable and management is low-cost. Example: ADR $160 x 0.6 occupancy = $35,040 revenue; 35% expenses = $22,776 NOI; price $300,000 => 7.6% cap.
• Risk: Title clarity, neighborhood safety perception, and tourist season concentration. Strong local marketing drives repeat visitors.

6) Northern Japan (Hokkaido) — Nature, winter sports, and a rising off-season

• Why now: Japan’s inbound tourism has matured post-2022–25 recovery; Hokkaido offers both winter-sports crowds and summer nature tourism.
• Property type: Chalets, ryokan-style guesthouses, serviced apartments.
• Seasonality: Peak Dec–Mar (winter) and Jul–Aug (summer). Shoulder demand for fall foliage.
• Sample metrics: ADR ¥18,000–¥45,000; occupancy 48%–68%.
• Sample cap-rate: 4.5%–7%. Expect higher management costs for language/guest services.
• Risk: Operational complexity and reliance on inbound international travel patterns; partner with bilingual managers and tour operators.

7) Secondary U.S. Coastal Towns (e.g., Outer Banks-type markets) — Family-oriented rentals

• Why now: Families and larger groups prefer less-crowded coastal towns with good road access. These markets are less likely to face heavy urban STR regulation.
• Property type: 3–5 bed single-family homes with outdoor amenities.
• Seasonality: Peak May–Sep; shoulder demand from fall festivals and winter retreats in some areas.
• Sample metrics: ADR $275–$900 for large homes; occupancy 40%–75% depending on season.
• Sample cap-rate: 6%–10% for off-peak buys with strong summer ADR. Example: ADR $475 x 0.6 occupancy = $103,995 revenue; 42% expenses = $60,376 NOI; price $700,000 => 8.6% cap.
• Risk: Insurance and storm exposure in coastal markets; budget for higher property and backup power and flood insurance.

How to run the numbers quickly: a micro-model you can use on a phone

Use this quick formula to triage deals in 10 minutes:

1. Estimate Annual Revenue = ADR x 365 x Expected Occupancy Rate
2. Estimate Operating Expenses = Annual Revenue x Operating Expense Ratio (use 35%–45% for most STRs)
3. NOI = Annual Revenue - Operating Expenses
4. Cap Rate = NOI / Purchase Price

Example (coastal villa): ADR $350, Occupancy 55% => Revenue $70,388. Expenses 45% => NOI $38,713. Purchase $650,000 => Cap ≈ 6.0%.

Seasonality tactics: extract more revenue from each market

• Dynamic pricing with local event overlays: Use tools to lift ADR for high-demand weekends and local festivals tied to travel coverage.
• Shoulder-season packages: Add work-from-home week discounts (4+ week stays), adventure add-ons, or co-marketed experiences (chefs, guides) to increase length-of-stay during shoulder months. See a broader playbook for micro-events and pop-ups in the Micro-Events, Pop‑Ups and Resilient Backends.
• Target niches: Promote midweek stays to travelers seeking off-season experiences, remote workers, and digital nomads — higher yields in otherwise slow months. For slow-travel positioning and boutique stays, consult the Slow Travel & Boutique Stays playbook.

Regulation & compliance checklist for 2026 (don’t skip this)

• Confirm short-term rental permits and local caps.
• Validate TOT collection and remittance procedures; request historical TOT receipts if possible.
• Check HOA restrictions and insurance coverage for STR use.
• Understand platform-specific rules (e.g., local registration IDs required by Airbnb/VRBO in many jurisdictions).
• Plan a contingency: set aside a regulatory reserve (3–6 months of operating expenses) for sudden permit moratoriums or temporary suspensions.

Marketing & listing plays for 2026: make your property a travel story

TPG-style mentions drive demand — but you don’t need press to achieve high occupancy. Use these 2026-forward tactics:

• Experience-first listings: Lead with a short narrative on your listing page: what the stay feels like, not just the amenities. Use guest-focused photos showing experiences (sunrise surf, home-cooked dining, workspace views).
• Local partnerships: Partner with local experiences (guides, chefs, surf schools) and co-promote on socials. Bundled experiences boost ADR and create sharable content that travel publications notice.
• Video-first approach: Short reels and reels-optimized clips increase discovery on Instagram and TikTok — see best practices for short-form clipping and distribution in Short-Form Live Clips.
• Verified listings & trust signals: Use host verifications, local permit numbers, professional photography, and 3D tours & photography toolkits to increase conversions — especially post-pandemic when verification matters more.

Advanced 2026 strategies for scaling

• Portfolio diversification: Mix high-ADR, high-seasonality properties with steadier-income secondary-city stays to smooth cash flow.
• Professionalization: Use centralized PMS and channel managers to scale without losing quality. Consolidated reviews and consistent branding increase direct bookings (lower commission costs).
• Tax optimization: Plan for local tax regimes and consider cost segregation studies for U.S. properties to accelerate depreciation where legal.
• Exit thinking: Stage properties for broad appeal so they sell to both investors and owner-occupiers if rules change; keep capex attractive but not hyper-personalized.

Case study (quick): Turning a TPG-hotlist mention into bookings

“After a regional travel article named our coastal village a 2026 pick, we doubled shoulder-season demand by launching a curated surf-and-remote-work package.”

Scenario: A 3-bed coastal home with previously 40% annual occupancy averaged ADR $300. After targeted PR, video content, and a 3-night minimum remote-work package, occupancy rose to 60% and ADR to $325 on key weeks. That shifted a borderline 4.5% cap to ~6.5% within a year. The cost: $12k in marketing + minor upgrades — paid off in 10 months.

Deal-sourcing & negotiation tips for 2026

• Source off-market via local agents and hosts exiting due to regulation changes.
• Negotiate with contingency clauses tied to permit transferability and a short due-diligence window for TOT records.
• Bundle management: Offer sellers transition assistance (paying for next 3 months’ management) to secure better pricing and fast onboarding of the listing.

Final checklist before you write an offer

1. Run the 10-minute micro-model (ADR x occupancy -> NOI -> cap rate).
2. Confirm local STR permits and TOT history.
3. Budget for a conservative season (subtract 10–20% occupancy) and calculate break-even occupancy.
4. Get written estimates from two local managers for management fees and operational forecasts.
5. Plan marketing launch (photo + short-form video + one local partnership) before closing to capture demand momentum.

Closing: The best buys marry press momentum with realistic economics

In 2026, travel-hotlist mentions (like those in The Points Guy’s 2026 roundup) are a starting pistol — they signal attention. The winning investments take that signal and pair it with local STR metrics, regulatory clarity, and a marketing plan that turns interest into revenue. Use the frameworks and sample math in this guide to triage, underwrite, and scale vacation rentals that actually perform.

Call to action

Ready to vet a property? Download our 10-minute STR underwriting template and seasonal marketing checklist (free for subscribers) or book a 30-minute review with our investments desk to get a tailored cap-rate sketch for any listing on your short list. Act now — travel trends move fast in 2026, and the best windows close in a single convention season.

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