What is the best time of year to visit Naples, Florida?

Naples' peak season runs December through April when snowbirds arrive for warm weather and Naples' full social calendar. Shoulder seasons — November and May through early June — offer excellent weather at more accessible prices. Summer offers significantly lower rates with less crowded beaches. Golfers particularly benefit from summer visits with reduced course rates and exceptional course conditions.

What types of vacation rentals are available in Naples?

Naples vacation rentals range from studio condominiums to six-bedroom Gulf-front estates in Olde Naples and Port Royal. Options include Gulf-front condominiums in Pelican Bay and Vanderbilt Beach, waterfront homes with private boat docks in Aqualane Shores and Royal Harbor, golf community residences in Grey Oaks and Mediterra, and estate homes near 5th Avenue South.

What is the price range for Naples vacation rentals?

Naples vacation rental prices range from approximately $5,000 to $15,000 per month for condominiums during peak season, $8,000 to $30,000 for single-family homes, and $50,000 to over $125,000 per month for Gulf-front estates in Olde Naples and Port Royal. Off-season rates are typically 30-50% lower than peak season pricing.

Are pets allowed in Naples vacation rentals?

Pet policies vary by individual property. Some Naples vacation rentals are fully pet-friendly, others allow small dogs only, and others do not permit pets. Contact Alpizar & Company directly to identify which properties accommodate your specific pet. Pet deposits and fees are common even in pet-friendly properties.

Can I bring my boat to a Naples vacation rental?

Yes — many Naples vacation rentals include private boat docks. Our waterfront vacation category features properties with private dock access. Canal depths, bridge clearances, and Gulf access routes vary by location. Contact us with your vessel specifications and we can match you to properties that accommodate your boat.

How do I book a Naples vacation rental with Alpizar & Company?

Browse available listings on this page or use the experience category tiles to search by vacation type. Contact us at (239) 438-1102 or use the contact form to confirm availability and book. We offer complimentary, pressure-free assistance finding the right rental — and if you fall in love with Naples, our real estate team is ready to help you explore ownership options.

Naples Vacation Rentals | Beach, Golf, Waterfront & More

$1,850

1085 Forest Lakes Dr 8305, NAPLES

1 Bed 1 Bath 766 SqFt Rental MLS® # 226015333

Supreme Rental Solutions PM

$1,800

1315 Mainsail Dr 1113, NAPLES

2 Beds 2 Baths 815 SqFt Rental MLS® # 226031326

eXp Realty LLC

$1,800

573 Cape Florida Ln, NAPLES

3 Beds 2 Baths 1,488 SqFt Rental MLS® # 226018783

Realty One Group MVP

$1,800

↓ $200

2855 Cypress Trace Cir 102, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226020197

Prime Real Estate of Naples

$1,800

1075 Foxfire Ln 201, NAPLES

2 Beds 1 Bath 843 SqFt Rental MLS® # 226022672

Realty One Group MVP

$1,790

↓ $100

1180 Reserve Way 302, NAPLES

1 Bed 1 Bath 850 SqFt Rental MLS® # 226012943

Realty Hub

$1,780

4625 Bayshore Dr D8, NAPLES

2 Beds 2 Baths 886 SqFt Rental MLS® # 226020789

Ivanova Realty LLC

$1,700

↓ $100

1010 Manatee Rd B304, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226006279

MDM Naples Real Estate LLC

$1,690

↓ $210

9554 Trevi Ct 4715, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226008372

Downing Frye Realty Inc.

$1,650

332 Charlemagne Blvd H101, NAPLES

2 Beds 2 Baths 1,082 SqFt Rental MLS® # 226032169

Premiere Plus Realty Company

$1,600

5515 Rattlesnake Hammock Rd 205, NAPLES

2 Beds 2 Baths 1,060 SqFt Rental MLS® # 226031541

ERA Naples Realty Services

$1,600

↓ $150

N/A, NAPLES

2 Beds 2 Baths 1,308 SqFt Rental MLS® # 226013588

Sun Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$1,850

1085 Forest Lakes Dr 8305, NAPLES

$1,800

1315 Mainsail Dr 1113, NAPLES

$1,800

573 Cape Florida Ln, NAPLES

$1,800

2855 Cypress Trace Cir 102, NAPLES

$1,800

1075 Foxfire Ln 201, NAPLES

$1,790

1180 Reserve Way 302, NAPLES

$1,780

4625 Bayshore Dr D8, NAPLES

$1,700

1010 Manatee Rd B304, NAPLES

$1,690

9554 Trevi Ct 4715, NAPLES

$1,650

332 Charlemagne Blvd H101, NAPLES

$1,600

5515 Rattlesnake Hammock Rd 205, NAPLES

$1,600

N/A, NAPLES