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

$15,000

5550 Heron Point Dr 704, NAPLES

2 Beds 2 Baths 1,514 SqFt Rental MLS® # 226025708

Berkshire Hathaway FL Realty

$15,000

3115 Gulf Shore Blvd N 203s, NAPLES

2 Beds 2 Baths 1,505 SqFt Rental MLS® # 226025132

Compass Florida LLC

$15,000

4001 Gulf Shore Blvd N 702, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226024507

Downing Frye Realty Inc.

$15,000

4031 Gulf Shore Blvd N 11-c, NAPLES

2 Beds 2 Baths 2,176 SqFt Rental MLS® # 226024347

Naples Homes and Rentals Inc

$15,000

3402 Tigris Ln, NAPLES

4 Beds 4 Baths 2,800 SqFt Rental MLS® # 226024051

Realty One Group MVP

$15,000

400 Flagship Dr 302, NAPLES

3 Beds 3 Baths 2,035 SqFt Rental MLS® # 226023578

SunStream Realty

$15,000

14831 Dockside Ln, NAPLES

4 Beds 4 Baths 2,942 SqFt Rental MLS® # 226022442

Coldwell Banker Realty

$15,000

1100 8th Ave S 123f, NAPLES

2 Beds 2 Baths 1,440 SqFt Rental MLS® # 226021935

John R Wood Properties

$15,000

↑ $11,000

1125 Central Ave 462, NAPLES

2 Beds 2 Baths 1,858 SqFt Rental MLS® # 226022022

Achieve Realty LLC

$15,000

914 Marble Dr, NAPLES

3 Beds 2 Baths 1,715 SqFt Rental MLS® # 226021936

Waterfront Realty Group Inc

$15,000

4901 Gulf Shore Blvd N 104, NAPLES

2 Beds 2 Baths 1,913 SqFt Rental MLS® # 226018191

William Raveis Real Estate

$15,000

530 108th Ave N, NAPLES

3 Beds 2 Baths 1,350 SqFt Rental MLS® # 226020932

Naples Vibe Realty, LLC

$15,000

295 Grande Way 1006, NAPLES

3 Beds 4 Baths 2,964 SqFt Rental MLS® # 226019060

William Raveis Real Estate

$15,000

295 Grande Way 1006, NAPLES

3 Beds 4 Baths 2,964 SqFt Rental MLS® # 226019053

William Raveis Real Estate

$15,000

13528 Mandarin Cir, NAPLES

5 Beds 4 Baths 3,359 SqFt Rental MLS® # 2026020290

Blue Lighthouse Realty Inc

$15,000

2950 Coach House Ln, NAPLES

4 Beds 2 Baths 2,292 SqFt Rental MLS® # 226018447

Staton Properties, LLC

$15,000

5550 Heron Point Dr 1804, NAPLES

3 Beds 2 Baths 1,514 SqFt Rental MLS® # 226009232

Compass Florida LLC

$15,000

↑ $2,500

2875 Coco Lakes Dr, NAPLES

5 Beds 6 Baths 4,470 SqFt Rental MLS® # 226018058

Premiere Plus Realty Company

$15,000

5964 Pelican Bay Blvd 434, NAPLES

2 Beds 2 Baths 1,436 SqFt Rental MLS® # 226018032

Royal Shell Real Estate, Inc.

$15,000

410 Flagship Dr 1105, NAPLES

3 Beds 3 Baths 1,860 SqFt Rental MLS® # 226017635

Downing Frye Realty Inc.

$15,000

10701 Gulf Shore Dr 1200, NAPLES

3 Beds 3 Baths 2,331 SqFt Rental MLS® # 226017544

WeichertRealtors-ParadiseHomes

$15,000

28864 Blaisdell Dr, NAPLES

4 Beds 5 Baths 3,238 SqFt Rental MLS® # 226017121

RMC REALTY INTERNATIONAL

$15,000

300 Dunes Blvd Ph-5, NAPLES

3 Beds 2 Baths 1,893 SqFt Rental MLS® # 226016133

William Raveis Real Estate

$15,000

4530 Gulf Shore Blvd N 2-122, NAPLES

3 Beds 3 Baths 1,786 SqFt Rental MLS® # 226014164

Premier Sotheby's Int'l Realty

$15,000

10701 Gulf Shore Dr 302, NAPLES

2 Beds 2 Baths 1,560 SqFt Rental MLS® # 226014821

WeichertRealtors-ParadiseHomes

$15,000

8229 Allendale Ct, NAPLES

3 Beds 3 Baths 2,930 SqFt Rental MLS® # 226013298

Realty One Group MVP

$15,000

513 96th Ave N, NAPLES

3 Beds 2 Baths 1,770 SqFt Rental MLS® # 226013438

ALL IN PROPERTY MANAGEMENT LLC

$15,000

711 91st Ave N, NAPLES

4 Beds 2 Baths 1,600 SqFt Rental MLS® # 226012215

Naples Vibe Realty, LLC

$15,000

2700 Lantern Ln, NAPLES

4 Beds 3 Baths 3,095 SqFt Rental MLS® # 226011146

Royal Shell Real Estate, Inc.

$15,000

6573 Marissa Loop 1902, NAPLES

2 Beds 2 Baths 1,341 SqFt Rental MLS® # 226009879

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$15,000

5550 Heron Point Dr 704, NAPLES

$15,000

3115 Gulf Shore Blvd N 203s, NAPLES

$15,000

4001 Gulf Shore Blvd N 702, NAPLES

$15,000

4031 Gulf Shore Blvd N 11-c, NAPLES

$15,000

3402 Tigris Ln, NAPLES

$15,000

400 Flagship Dr 302, NAPLES

$15,000

14831 Dockside Ln, NAPLES

$15,000

1100 8th Ave S 123f, NAPLES

$15,000

1125 Central Ave 462, NAPLES

$15,000

914 Marble Dr, NAPLES

$15,000

4901 Gulf Shore Blvd N 104, NAPLES

$15,000

530 108th Ave N, NAPLES

$15,000

295 Grande Way 1006, NAPLES

$15,000

295 Grande Way 1006, NAPLES

$15,000

13528 Mandarin Cir, NAPLES

$15,000

2950 Coach House Ln, NAPLES

$15,000

5550 Heron Point Dr 1804, NAPLES

$15,000

2875 Coco Lakes Dr, NAPLES

$15,000

5964 Pelican Bay Blvd 434, NAPLES

$15,000

410 Flagship Dr 1105, NAPLES

$15,000

10701 Gulf Shore Dr 1200, NAPLES

$15,000

28864 Blaisdell Dr, NAPLES

$15,000

300 Dunes Blvd Ph-5, NAPLES

$15,000

4530 Gulf Shore Blvd N 2-122, NAPLES

$15,000

10701 Gulf Shore Dr 302, NAPLES

$15,000

8229 Allendale Ct, NAPLES

$15,000

513 96th Ave N, NAPLES

$15,000

711 91st Ave N, NAPLES

$15,000

2700 Lantern Ln, NAPLES

$15,000

6573 Marissa Loop 1902, NAPLES