Local guides, from Central Virginia to the country’s top vacation-rental markets
Start at home: the Central Virginia guides help everyone, whether you’re buying a home to live in or a place to rent. Then explore 25 of the country’s most popular vacation-rental markets, each with short-term rental rules from official sources.
Central Virginia
Buying your first home, your next home, a lake place or a rental? These guides cover the towns, counties and rules that matter most around Charlottesville.
Buying a home to live in
First-time and move-up buyers in Charlottesville, Albemarle, Crozet and nearby counties: loan options and Virginia Housing assistance in plain English.
Home buyer guide →Down payment assistance
Virginia Housing loans and grants (DPA Grant, CCA Grant, Plus Second) plus our own lender-specific down payment assistance. Register to learn more.
Down payment assistance →Charlottesville & Albemarle County
The 185-day homestay rule in the city, and Albemarle’s hosted-stay, 5-acre and 45-day limits.
Read the rules →Lake Anna
Buying a lake house at Lake Anna? Andy Zemon, voted Best of Lake Anna Best Mortgage Agent (Gold, 2025 & 2026), explains second-home vs. investment classification and Louisa County short-term rental rules.
Read the Lake Anna guide →Wintergreen
Buying a mountain home or condo at Wintergreen? Learn how lenders classify it, how WPOA rental registration and Nelson County licensing work, and why resort rental programs matter for your loan.
Read the Wintergreen guide →Smith Mountain Lake
Buying a vacation home or rental at Smith Mountain Lake? Check the county before you buy: Franklin, Bedford and Pittsylvania each regulate short-term rentals differently.
Read the Smith Mountain Lake guide →Massanutten
Buying at Massanutten? Rockingham County now requires an annual short-term rental permit. Here is how that interacts with second-home and investment-property financing.
Read the Massanutten guide →Top U.S. vacation-rental markets
25 markets chosen for traveler demand and investor interest in 2026 reports from AirDNA and Vrbo, plus my two featured favorites. Each guide summarizes the local short-term rental rules from official city, county or state sources (checked November 2026), HOA and insurance issues, and how the financing usually works.
Legend: Permit / registration Zoning or caps limit where Heavily restricted
Florida & the Gulf Coast
Destin & Fort Walton Beach, FL
Permit / registration
Emerald Coast beaches, family summer travel and a deep rental-management market make Destin and Fort Walton Beach a perennial second-home and vacation-rental favorite.
Read the guide →30A & Santa Rosa Beach (Walton County), FL
Permit / registration
The 30A corridor (Santa Rosa Beach, Seaside, Rosemary Beach and neighboring communities) pairs walkable beach towns with strong family-vacation demand.
Read the guide →Panama City Beach, FL
Permit / registration
Miles of Gulf beaches and a broad mix of condos and houses keep Panama City Beach among Vrbo’s trending summer beach destinations.
Read the guide →Fort Myers Beach & Southwest Florida, FL
Permit / registration
Fort Myers Beach, Sanibel and Captiva draw winter visitors and summer families alike, and Fort Myers was among Vrbo’s trending 2026 holiday searches.
Read the guide →Fort Lauderdale, FL
Permit / registration
Beaches, the cruise port and year-round sunshine give Fort Lauderdale steady leisure demand, and AirDNA’s 2026 report highlighted it among higher-budget leisure markets.
Read the guide →Orlando, Kissimmee & Celebration (Disney area), FL
Zoning or caps limit where
Orange County limits STRs to certain zones; Osceola County uses zoning plus state and county registration.
Read the guide →Southeast Coast
Savannah, GA
Heavily restricted
Historic squares, food and a walkable downtown make Savannah a strong leisure market, though AirDNA itself notes regulation makes the city center harder to enter.
Read the guide →Charleston, SC
Heavily restricted
Charleston’s history, dining and nearby beaches keep it on Vrbo’s trending beach-destination list, but the City’s residential STR rules are among the strictest in the Southeast.
Read the guide →Appalachians & Ozarks
Gatlinburg & Pigeon Forge (Smoky Mountains), TN
Permit / registration
The gateway to Great Smoky Mountains National Park, with cabins built for groups and families; AirDNA’s 2026 report called Gatlinburg/Pigeon Forge one of the most competitive investment markets, with yields helped by softer home prices.
Read the guide →Asheville & Western North Carolina, NC
Heavily restricted
Blue Ridge views, breweries and the Great Smoky Mountains nearby (Vrbo flagged Cherokee, NC among 2026’s fastest-growing holiday searches) keep Western North Carolina in demand.
Read the guide →Lake Norman, NC
Permit / registration
North Carolina’s largest man-made lake, just north of Charlotte, combines lake living with metro demand; AirDNA highlighted Lake Norman as a high-ADR mid-budget market.
Read the guide →Branson & the Ozark Mountains, MO
Zoning or caps limit where
Shows, lakes (Table Rock and Taneycomo) and family attractions drive Ozarks travel; AirDNA’s 2026 report named the Ozark Mountains a top leisure market in its sub-$1M tier.
Read the guide →Northeast
Pocono Mountains, PA
Zoning or caps limit where
A drive-to getaway for New York and Philadelphia with ski resorts, lakes and resort communities; AirDNA’s 2026 report cited the Poconos for strong yields at moderate prices.
Read the guide →Hudson Valley, NY
Zoning or caps limit where
Farm towns, Catskills hiking and a short trip from New York City; AirDNA’s 2026 report highlighted the Lower Hudson Valley among mid-budget markets.
Read the guide →Finger Lakes, NY
Zoning or caps limit where
Wineries, lakes and college towns (Ithaca, Geneva, Canandaigua) make the Finger Lakes a classic summer and fall getaway; AirDNA’s 2026 report listed it among its budget-tier markets.
Read the guide →The Hamptons (Long Island), NY
Heavily restricted
Ocean beaches and summer-season demand make the Hamptons one of the country’s highest-priced vacation markets; AirDNA’s 2026 report cited Long Island toward the Hamptons in its upper budget tier.
Read the guide →Cape Cod, MA
Permit / registration
Beaches, bay towns and summer tradition keep Cape Cod among Vrbo’s trending beach destinations.
Read the guide →Nantucket, MA
Permit / registration
An island classic with a short, intense summer season and premium pricing; Vrbo listed Nantucket among its trending beach destinations.
Read the guide →Mountain West & Southwest
Breckenridge, CO
Heavily restricted
A historic ski town with summer trails; a Breckenridge home was among Vrbo’s 2026 Vacation Rentals of the Year.
Read the guide →Estes Park (Rocky Mountain National Park), CO
Heavily restricted
The main gateway to Rocky Mountain National Park, which AirDNA’s 2026 report singled out as a favorite national-park market.
Read the guide →Big Sky, MT
Zoning or caps limit where
Big Sky Resort and the Yellowstone region; Big Sky was named to Vrbo’s Unpack ’26 Destinations of the Year.
Read the guide →Scottsdale & Phoenix, AZ
Permit / registration
Golf, spring training and winter sunshine; Vrbo’s 2026 holiday trends highlighted Phoenix and Old Town Scottsdale.
Read the guide →Pacific
Maui, HI
Heavily restricted
One of the most iconic U.S. vacation islands and on Vrbo’s trending beach list, but also the market with the most significant recent STR restrictions.
Read the guide →Seaside & the Oregon Coast, OR
Zoning or caps limit where
A family beach town within a drive of Portland; Vrbo reported Seaside searches up more than 30% for summer 2026.
Read the guide →Caribbean
St. John, USVI
Permit / registration
USVI hotel room tax and business licensing; cisterns and island insurance.
Read the guide →How these markets were chosen: AirDNA, “Best Places to Invest in Short-Term Rentals in 2026” (Jan 27, 2026) incl. budget-tier & demand-driver breakouts · Expedia Group / Vrbo, Unpack ’26 trends (Destinations of the Year) · Vrbo, “Beach Readaways” summer 2026 trending destinations · Vrbo, trending Fourth of July 2026 destinations (search growth) · Vrbo, 2026 Vacation Rentals of the Year. Orlando/Kissimmee and St. John are Andy’s featured markets. Inclusion isn’t a recommendation to buy; some of these markets restrict short-term rentals heavily, and the guides say so.
Talk through your purchase with Andy
Tell me the town, the property and how you plan to use it. I’ll tell you how a lender is likely to classify it, which local rules to check and what to gather before you make an offer.