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

$14,000

10562 Gulf Shore Dr 202, NAPLES

2 Beds 2 Baths 1,227 SqFt Rental MLS® # 226013613

William Raveis Real Estate

$14,000

450 Launch Cir 602, NAPLES

3 Beds 2 Baths 1,480 SqFt Rental MLS® # 226028551

John R Wood Properties

$14,000

9387 Vercelli Ct, NAPLES

4 Beds 2 Baths 2,242 SqFt Rental MLS® # 226018663

WeichertRealtors-ParadiseHomes

$14,000

2830 Tiburon Blvd E 103, NAPLES

3 Beds 2 Baths 2,508 SqFt Rental MLS® # 226025141

William Raveis Real Estate

$14,000

700 Bentwater Cir 104, NAPLES

3 Beds 3 Baths 1,831 SqFt Rental MLS® # 226026639

John R Wood Properties

$14,000

300 Dunes Blvd 105, NAPLES

3 Beds 2 Baths 1,893 SqFt Rental MLS® # 226024333

Naples Homes and Rentals Inc

$14,000

9215 Veneto Ln, NAPLES

2 Beds 3 Baths 1,854 SqFt Rental MLS® # 226023505

WeichertRealtors-ParadiseHomes

$14,000

9200 Mercato Way, NAPLES

3 Beds 4 Baths 2,708 SqFt Rental MLS® # 226022638

Premier Sotheby's Int'l Realty

$14,000

712 Shadow Lake Ln, NAPLES

3 Beds 3 Baths 2,768 SqFt Rental MLS® # 226021881

John R Wood Properties

$14,000

400 Flagship Dr 905, NAPLES

3 Beds 3 Baths 1,750 SqFt Rental MLS® # 226018453

William Raveis Real Estate

$14,000

837 Sailaway Ln 204, NAPLES

3 Beds 3 Baths 1,831 SqFt Rental MLS® # 226018155

Compass Florida LLC

$14,000

7112 Falcons Glen Blvd, NAPLES

3 Beds 2 Baths 1,786 SqFt Rental MLS® # 226015289

Coldwell Banker Realty

$14,000

7771 Cottesmore Dr, NAPLES

3 Beds 3 Baths 2,481 SqFt Rental MLS® # 226015867

Premier Sotheby's Int'l Realty

$14,000

3443 Gulf Shore Blvd N 809, NAPLES

2 Beds 2 Baths 1,164 SqFt Rental MLS® # 226011646

Downing Frye Realty Inc.

$14,000

400 Flagship Dr 501, NAPLES

3 Beds 2 Baths 1,734 SqFt Rental MLS® # 226010504

Downing Frye Realty Inc.

$14,000

1125 Central Ave 373, NAPLES

2 Beds 3 Baths 1,787 SqFt Rental MLS® # 226011039

WeichertRealtors-ParadiseHomes

$14,000

7638 Pebble Creek Cir 204, NAPLES

3 Beds 2 Baths 1,526 SqFt Rental MLS® # 226007350

Downing Frye Realty Inc.

$14,000

8924 Ventura Way, NAPLES

3 Beds 3 Baths 2,098 SqFt Rental MLS® # 226007272

Downing Frye Realty Inc.

$14,000

3215 Gulf Shore Blvd N 704n, NAPLES

2 Beds 3 Baths 1,505 SqFt Rental MLS® # 226005679

William Raveis Real Estate

$14,000

10851 Gulf Shore Dr 301, NAPLES

3 Beds 2 Baths 2,003 SqFt Rental MLS® # 2026004273

Coldwell Banker Realty

$14,000

↑ $6,500

16907 Fairgrove Way 201, NAPLES

3 Beds 2 Baths 2,376 SqFt Rental MLS® # 225084679

Real Broker, LLC

$14,000

6101 Pelican Bay Blvd 1805, NAPLES

2 Beds 2 Baths 1,337 SqFt Rental MLS® # 226001359

John R Wood Properties

$14,000

↓ $3,000

9675 Moonflower Ct, NAPLES

4 Beds 4 Baths 3,033 SqFt Rental MLS® # 225083939

John R Wood Properties

$14,000

1901 Winding Oaks Way, NAPLES

3 Beds 3 Baths 2,976 SqFt Rental MLS® # 225082862

Royal Shell Real Estate, Inc.

$14,000

↑ $5,000

7128 Lemuria Cir 702, NAPLES

3 Beds 4 Baths 2,408 SqFt Rental MLS® # 225080143

John R Wood Properties

$14,000

9446 Piacere Way, NAPLES

3 Beds 2 Baths 2,249 SqFt Rental MLS® # 225079549

Safe Harbor Real Estate Servic

$14,000

5897 Chanteclair Dr 313, NAPLES

2 Beds 2 Baths 1,506 SqFt Rental MLS® # 225077832

William Raveis Real Estate

$14,000

↑ $2,000

7671 Pebble Creek Cir 303, NAPLES

3 Beds 2 Baths 1,641 SqFt Rental MLS® # 225074250

Premier Sotheby's Int'l Realty

$14,000

4155 Crayton Rd 203, NAPLES

3 Beds 3 Baths 1,940 SqFt Rental MLS® # 225074233

Premier Sotheby's Int'l Realty

$14,000

4005 Gulf Shore Blvd N 607, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225074195

Premier Sotheby's Int'l Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$14,000

10562 Gulf Shore Dr 202, NAPLES

$14,000

450 Launch Cir 602, NAPLES

$14,000

9387 Vercelli Ct, NAPLES

$14,000

2830 Tiburon Blvd E 103, NAPLES

$14,000

700 Bentwater Cir 104, NAPLES

$14,000

300 Dunes Blvd 105, NAPLES

$14,000

9215 Veneto Ln, NAPLES

$14,000

9200 Mercato Way, NAPLES

$14,000

712 Shadow Lake Ln, NAPLES

$14,000

400 Flagship Dr 905, NAPLES

$14,000

837 Sailaway Ln 204, NAPLES

$14,000

7112 Falcons Glen Blvd, NAPLES

$14,000

7771 Cottesmore Dr, NAPLES

$14,000

3443 Gulf Shore Blvd N 809, NAPLES

$14,000

400 Flagship Dr 501, NAPLES

$14,000

1125 Central Ave 373, NAPLES

$14,000

7638 Pebble Creek Cir 204, NAPLES

$14,000

8924 Ventura Way, NAPLES

$14,000

3215 Gulf Shore Blvd N 704n, NAPLES

$14,000

10851 Gulf Shore Dr 301, NAPLES

$14,000

16907 Fairgrove Way 201, NAPLES

$14,000

6101 Pelican Bay Blvd 1805, NAPLES

$14,000

9675 Moonflower Ct, NAPLES

$14,000

1901 Winding Oaks Way, NAPLES

$14,000

7128 Lemuria Cir 702, NAPLES

$14,000

9446 Piacere Way, NAPLES

$14,000

5897 Chanteclair Dr 313, NAPLES

$14,000

7671 Pebble Creek Cir 303, NAPLES

$14,000

4155 Crayton Rd 203, NAPLES

$14,000

4005 Gulf Shore Blvd N 607, NAPLES