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

$4,000

↓ $1,000

975 Tarpon Cove Dr 204, NAPLES

3 Beds 2 Baths 1,340 SqFt Rental MLS® # 226019379

Hovland Realty, LLC

$4,000

5 High Point Cir W 104, NAPLES

2 Beds 2 Baths 871 SqFt Rental MLS® # 226029947

Downing Frye Realty Inc.

$4,000

290 Naples Cove Dr 2602, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226012248

Grice Realty Inc

$4,000

3029 Driftwood Way 3303, NAPLES

2 Beds 2 Baths 1,248 SqFt Rental MLS® # 226028283

Century 21 AllPoints Realty

$4,000

7794 Emerald Cir A-102, NAPLES

2 Beds 2 Baths 1,022 SqFt Rental MLS® # 226028289

Premier Property Management

$3,995

6075 Pelican Bay Blvd 1204, NAPLES

2 Beds 3 Baths 1,800 SqFt Rental MLS® # 226021246

Premier Property Management

$3,975

↓ $225

4082 Belair Ln 9, NAPLES

3 Beds 2 Baths 1,525 SqFt Rental MLS® # 226007848

DomainRealty.com LLC

$3,950

↓ $150

9418 Greyhawk Trl, NAPLES

3 Beds 2 Baths 2,107 SqFt Rental MLS® # 226014316

Compass Florida LLC

$3,950

410 Broad Ave S H410, NAPLES

2 Beds 2 Baths 890 SqFt Rental MLS® # 226025390

John R Wood Properties

$3,900

↓ $300

771 94th Ave N, NAPLES

3 Beds 2 Baths 1,430 SqFt Rental MLS® # 226000751

A Plus Realty

$3,900

1896 Crestview Way A47, NAPLES

2 Beds 2 Baths 1,723 SqFt Rental MLS® # 2026018669

Weichert Realtors Capella Estates

$3,900

41 High Point Cir S 104, NAPLES

2 Beds 2 Baths 1,015 SqFt Rental MLS® # 225078050

John R Wood Properties

$3,900

5792 Deauville Cir A103, NAPLES

2 Beds 2 Baths 1,209 SqFt Rental MLS® # 226019720

Coldwell Banker Realty

$3,895

N/A, NAPLES

2 Beds 2 Baths 1,647 SqFt Rental MLS® # 226024811

Fast Action Realty Inc

$3,850

465 Robin Hood Cir 101, NAPLES

3 Beds 2 Baths 1,630 SqFt Rental MLS® # 225080399

Waterfront Realty Group Inc

$3,850

7754 Emerald Cir T202, NAPLES

2 Beds 2 Baths 1,022 SqFt Rental MLS® # 226026919

Downing Frye Realty Inc.

$3,800

↓ $450

401 Bayfront Pl 3207, NAPLES

2 Beds 2 Baths 1,344 SqFt Rental MLS® # 226005333

Serhant-Naples

$3,800

8110 Calle Canovas St S, NAPLES

2 Beds 2 Baths 1,558 SqFt Rental MLS® # 226025720

REMAX Affinity Mercato

$3,800

717 Landover Cir 103, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226020001

Berkshire Hathaway FL Realty

$3,800

7719 Jewel Ln 103, NAPLES

2 Beds 2 Baths 1,022 SqFt Rental MLS® # 226019996

Berkshire Hathaway FL Realty

$3,800

320 14th Ave S 320e, NAPLES

2 Beds 2 Baths 1,090 SqFt Rental MLS® # 226024825

Waterfront Realty Group Inc

$3,800

↓ $200

850 29th St Sw, NAPLES

4 Beds 2 Baths 2,179 SqFt Rental MLS® # 226015859

Waterfront Realty Group Inc

$3,800

1130 Partridge Cir 102, NAPLES

2 Beds 2 Baths 1,191 SqFt Rental MLS® # 226005236

Grice Realty Inc

$3,800

↑ $300

15616 Marcello Cir, NAPLES

3 Beds 3 Baths 1,580 SqFt Rental MLS® # 226026177

Premiere Plus Realty Company

$3,800

↑ $300

1455 Tiffany Ln 107, NAPLES

2 Beds 2 Baths 1,536 SqFt Rental MLS® # 226010652

Grice Realty Inc

$3,800

218 Gabriel Cir 3809, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 225078082

Downing Frye Realty Inc.

$3,800

8098 Tauren Ct, NAPLES

3 Beds 2 Baths 2,000 SqFt Rental MLS® # 226011051

John R Wood Properties

$3,800

↓ $90

552 97th Ave N, NAPLES

3 Beds 2 Baths 1,612 SqFt Rental MLS® # 226019230

Starlink Realty, Inc

$3,800

↓ $200

5954 Pelican Bay Blvd 222, NAPLES

2 Beds 2 Baths 1,436 SqFt Rental MLS® # 226016163

William Raveis Real Estate

$3,800

3563 Antarctic Cir 2102, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226017918

KW Elevate Luxury

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$4,000

975 Tarpon Cove Dr 204, NAPLES

$4,000

5 High Point Cir W 104, NAPLES

$4,000

290 Naples Cove Dr 2602, NAPLES

$4,000

3029 Driftwood Way 3303, NAPLES

$4,000

7794 Emerald Cir A-102, NAPLES

$3,995

6075 Pelican Bay Blvd 1204, NAPLES

$3,975

4082 Belair Ln 9, NAPLES

$3,950

9418 Greyhawk Trl, NAPLES

$3,950

410 Broad Ave S H410, NAPLES

$3,900

771 94th Ave N, NAPLES

$3,900

1896 Crestview Way A47, NAPLES

$3,900

41 High Point Cir S 104, NAPLES

$3,900

5792 Deauville Cir A103, NAPLES

$3,895

N/A, NAPLES

$3,850

465 Robin Hood Cir 101, NAPLES

$3,850

7754 Emerald Cir T202, NAPLES

$3,800

401 Bayfront Pl 3207, NAPLES

$3,800

8110 Calle Canovas St S, NAPLES

$3,800

717 Landover Cir 103, NAPLES

$3,800

7719 Jewel Ln 103, NAPLES

$3,800

320 14th Ave S 320e, NAPLES

$3,800

850 29th St Sw, NAPLES

$3,800

1130 Partridge Cir 102, NAPLES

$3,800

15616 Marcello Cir, NAPLES

$3,800

1455 Tiffany Ln 107, NAPLES

$3,800

218 Gabriel Cir 3809, NAPLES

$3,800

8098 Tauren Ct, NAPLES

$3,800

552 97th Ave N, NAPLES

$3,800

5954 Pelican Bay Blvd 222, NAPLES

$3,800

3563 Antarctic Cir 2102, NAPLES