Good — here’s a practical, step-by-step plan to find a small specialist (not a multinational) that has proven hospitality experience and can redesign your boutique Caribbean hotel website, plus tools, questions, and negotiation tips you can use immediately.

1. Define exactly what you need (so you can compare apples-to-apples)

• Scope: full redesign or visual + copy refresh? New booking engine integration? Channel manager/OTA connectivity? Multilingual? Mobile-first/responsive? Accessibility (WCAG)? SEO migration? CMS preference (WordPress, Webflow, headless)?
• Deliverables & success metrics: pages, templates, booking funnel conversion target, page-speed threshold, SEO traffic retention, launch date.
• Tech constraints: current PMS/booking provider, analytics, any proprietary systems.
• Budget range and timeline (give a realistic window, eg “target launch 12–16 weeks” or “high season in Q2 — must be live by X date”).

2. Where to find the right small, hospitality-focused agencies

• Niche agency directories: search for “hotel website agency,” “hospitality web design agency,” or “boutique hotel website design” + region. Look for portfolio case studies with hotels.
• Design networks and directories: Awwwards, CSS Design Awards, Dribbble, Behance — filter for hospitality projects and check agency profiles.
• Industry channels: hotel tech conferences (Speakers/Partners lists), hospitality trade publications and blogs often list agencies; also LinkedIn groups for hotel owners/operators.
• Marketplaces for vetted specialists: Upwork (top-rated agencies/freelancers), Toptal (for senior freelancers), and Clutch.co (filter by company size, location, industry focus and read verified reviews).
• Local/regional options: look for small agencies based in the Caribbean, Central or South America — they often have lower rates and hospitality experience in the region. Search terms: “hotel website design [Caribbean island name]” or “hospitality web design Latin America.”
• Referrals: Ask peers — other boutique hotels, local tourism boards, or hotelier Facebook/Slack groups for recommendations. A referral from another hotel is high-value.

3. How to screen / shortlist candidates quickly

• Portfolio: only consider firms with 3–5 hotel websites in their portfolio (not just hospitality-themed visuals). Check for booking funnels, mobile experience, and evidence of performance (before/after conversion, speed, SEO).
• Case studies: prefer agencies that can show measurable results — increased direct bookings, reduced bounce, improved load times, or SEO recovery after migration.
• Size & culture fit: choose agencies with team size matching your needs (small hotel — small/specialist agency often works best). Ask who will do the work (founder, senior PM, or outsourced juniors).
• Hospitality integrations: confirm experience integrating with your PMS, booking engine, channel manager, payment gateway, and OTA-driven promos.
• References: ask for 2 client references from hotels (similar size / market).

4. What to put in your RFP / Brief (short, copy-pasteable) Include:

• Hotel overview: boutique positioning, number of rooms, markets, target guests.
• Project goals: e.g., “Increase direct bookings by X%,” “improve mobile conversion,” “lower booking abandonment,” or “modernize brand presentation.”
• Scope: number of pages, blog, languages, booking engine integration, analytics, SEO migration, CMS access, training.
• Current stack: CMS, booking engine, PMS, analytics, existing hosting, domain, SSL.
• Timeline & budget range.
• Deliverables & acceptance criteria: staging site, QA checklist, SEO checklist, migration plan, 30–90 day post-launch support.
• Ask for: team bios, project timeline & milestones, fixed or phased pricing, payment schedule, two client case studies with contact info, post-launch support costs.

5. Interview / vetting questions to ask shortlisted agencies

• “Which 3 hotel sites in your portfolio are most similar to ours and why?”
• “Describe a hotel project where you improved direct bookings — what did you change and what were results?”
• “How do you handle booking engine and PMS integrations? Which systems have you worked with?”
• “Who will be our day-to-day contact? Who does the design, front-end, back-end, SEO, and QA?”
• “How do you handle SEO migration to avoid traffic loss?”
• “What’s included in post-launch support, and how do you handle urgent fixes?”
• “Can you provide a staging URL and walkthrough of a recent hotel launch?”
• “What are the typical payment terms and what’s required upfront?”
• “How do you measure success and which KPIs will you track?”

6. Evaluation scorecard (simple, objective) Score each candidate 1–5 on:

• Hospitality experience & relevant portfolio
• Integrations & technical capability (booking engine, PMS)
• UX & mobile design quality
• Evidence of measurable results
• Communication & cultural fit
• Price vs scope & transparency
• Post-launch support & training

7. Negotiation and price-saving strategies

• Ask for phased approach: phase 1 (critical booking funnel + homepage + booking integration), phase 2 (content pages, blog, extras). This reduces upfront cost.
• Fixed-price milestones tied to deliverables to avoid ongoing open-ended fees.
• Provide content (copy, photos) yourself to reduce scope — but offer to buy photography package as an add-on.
• Use existing CMS templates or a lightweight solution (Webflow or WordPress with a hospitality theme) to cut dev hours.
• Offer a case-study/marketing testimonial in exchange for a lower rate (agencies value hotel success stories).
• Consider nearshore firms (Latin America/Caribbean) for lower rates but overlapping hours, or hire a senior freelance web designer + specialist developer instead of a full agency.

8. Red flags to avoid

• No hospitality case studies or only design mockups without live sites.
• Vague answers on SEO migration or booking integration.
• No clear ownership of post-launch bugs/support.
• Extremely low bid with no detail — likely to add costs later.
• Agency promises guaranteed search rankings or impossible conversion numbers.

9. Timeline & costs (guideline — not exact)

• Typical small agency redesign with booking integration: 8–16 weeks depending on scope.
• Cost ballpark (varies widely): for boutique/specialist small agencies you might see anywhere from low five-figures to high five-figures (USD). Freelancers or nearshore teams can be notably less. Use your budget range in the RFP to filter out unrealistic bids.

10. After selection — contract & launch checklist

• Contract: scope, timeline, milestones, IP ownership, payment schedule, warranties, and post-launch support terms.
• Pre-launch QA: cross-browser, device testing, booking flow end-to-end, analytics & goals, 301 redirect map for SEO, speed optimization.
• Analytics & tracking: ensure GA4, Search Console, booking conversion goals, and UTM strategy are set before launch.
• Rollback plan: how to revert if critical issues appear.
• 30–90 day support: ask for a fixed support period for bug fixes and performance tweaks.

11. Quick practical next steps (today)

• Draft a short RFP using the template above and post it on Clutch, Upwork, and email to 8–10 targeted agencies (mix of small US, nearshore, and regional Caribbean firms).
• Share 3 hotel websites you like and the biggest problems you face (slow conversions? high bounce?) — this helps agencies bid accurately.
• Ask for proposals within 7–10 days and schedule interviews with top 3.

If you want, I can:

• Draft a one-page RFP based on your hotel (I’ll need name, current CMS, booking engine, and high-level goals).
• Or search and shortlist 6–8 small hospitality-focused agencies/freelancers (include Caribbean/nearshore options) — I’ll need permission to browse the web for up-to-date recommendations.

Which would you prefer?