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

$4,500

581 Teryl Rd 5, NAPLES

2 Beds 2 Baths 1,403 SqFt Rental MLS® # 226017459

WeichertRealtors-ParadiseHomes

$4,500

3062 Sandpiper Bay Cir K302, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226009702

Coldwell Banker Realty

$4,500

4713 Arboretum Cir 202, NAPLES

2 Beds 2 Baths 1,480 SqFt Rental MLS® # 226025547

Royal Shell Real Estate, Inc.

$4,500

7896 Founders Cir, NAPLES

3 Beds 2 Baths 1,939 SqFt Rental MLS® # 226028470

REMAX Affinity Mercato

$4,500

7065 Dennis Cir F103, NAPLES

2 Beds 2 Baths 1,097 SqFt Rental MLS® # 226025549

Royal Shell Real Estate, Inc.

$4,500

6854 Sterling Greens Dr 201, NAPLES

3 Beds 2 Baths 1,727 SqFt Rental MLS® # 226023594

Berkshire Hathaway FL Realty

$4,500

6590 Beach Resort Dr 305, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 226023596

Berkshire Hathaway FL Realty

$4,500

7832 Meridan Ct, NAPLES

2 Beds 2 Baths 1,567 SqFt Rental MLS® # 226024759

EXIT Realty of Naples

$4,500

201 Albi Rd 2, NAPLES

2 Beds 2 Baths 1,542 SqFt Rental MLS® # 226023650

Napoli Realty Services, LLC

$4,500

6478 Waverly Green Way, NAPLES

3 Beds 3 Baths 1,711 SqFt Rental MLS® # 226004355

Woodruff Property Management

$4,500

900 L Ambiance Cir 9-106, NAPLES

2 Beds 2 Baths 1,389 SqFt Rental MLS® # 226026450

Waterfront Realty Group Inc

$4,500

2711 Citrus Lake Dr F302, NAPLES

2 Beds 2 Baths 1,272 SqFt Rental MLS® # 226000293

My Florida Real Estate, LLC

$4,500

↓ $300

228 Belina Dr 606, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226010590

William Raveis Real Estate

$4,400

229 Palm Dr 229-2, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 226028054

Bluewater Signature Realty LLC

$4,300

↓ $200

7310 Salerno Ct, NAPLES

3 Beds 2 Baths 1,540 SqFt Rental MLS® # 226005630

Naples Flat Fee Realty LLC

$4,300

↓ $700

4706 West Blvd W3, NAPLES

3 Beds 3 Baths 1,933 SqFt Rental MLS® # 226000557

DomainRealty.com LLC

$4,250

480 Bermuda Cove Way 1-104, NAPLES

2 Beds 2 Baths 1,372 SqFt Rental MLS® # 225083571

Star Rental & Property Mngt

$4,250

↓ $750

6954 Avalon Cir 707, NAPLES

3 Beds 2 Baths 1,725 SqFt Rental MLS® # 226014183

WeichertRealtors-ParadiseHomes

$4,250

3830 Sawgrass Way 2934, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226022329

Bluewater Signature Realty LLC

$4,250

4960 Deerfield Way E102, NAPLES

2 Beds 2 Baths 1,202 SqFt Rental MLS® # 226013996

Bluewater Signature Realty LLC

$4,250

3013 Futuna Ln, NAPLES

2 Beds 2 Baths 1,540 SqFt Rental MLS® # 2026012082

MAKS Realty Inc

$4,200

3950 Loblolly Bay Dr 3-402, NAPLES

2 Beds 2 Baths 1,185 SqFt Rental MLS® # 226016810

Premier Property Management

New New

$4,200

6960 Avalon Cir 807, NAPLES

3 Beds 2 Baths 1,725 SqFt Rental MLS® # 226030961

WeichertRealtors-ParadiseHomes

$4,200

↓ $300

7103 Lily Way, NAPLES

4 Beds 3 Baths 2,461 SqFt Rental MLS® # 226019856

Downing Frye Realty Inc.

$4,200

1299 Verde Dr 1503, NAPLES

3 Beds 2 Baths 1,744 SqFt Rental MLS® # 226019780

Downing Frye Realty Inc.

$4,200

↓ $100

1911 Morning Sun Lane, NAPLES

2 Beds 2 Baths 1,360 SqFt Rental MLS® # 225069690

Select Real Estate

$4,200

↓ $50

1910 Gulf Shore Blvd N 112, NAPLES

2 Beds 2 Baths 1,256 SqFt Rental MLS® # 225084242

REMAX Affinity Mercato

$4,200

2050 W Crown Pointe Blvd C214, NAPLES

3 Beds 2 Baths 1,267 SqFt Rental MLS® # 226017951

Coldwell Banker Realty

$4,200

613 Serendipity Dr 613, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226024742

William Raveis Real Estate

$4,200

3032 Woodside Ave, NAPLES

3 Beds 3 Baths 1,998 SqFt Rental MLS® # 226023598

Downing Frye Realty Inc.

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$4,500

581 Teryl Rd 5, NAPLES

$4,500

3062 Sandpiper Bay Cir K302, NAPLES

$4,500

4713 Arboretum Cir 202, NAPLES

$4,500

7896 Founders Cir, NAPLES

$4,500

7065 Dennis Cir F103, NAPLES

$4,500

6854 Sterling Greens Dr 201, NAPLES

$4,500

6590 Beach Resort Dr 305, NAPLES

$4,500

7832 Meridan Ct, NAPLES

$4,500

201 Albi Rd 2, NAPLES

$4,500

6478 Waverly Green Way, NAPLES

$4,500

900 L Ambiance Cir 9-106, NAPLES

$4,500

2711 Citrus Lake Dr F302, NAPLES

$4,500

228 Belina Dr 606, NAPLES

$4,400

229 Palm Dr 229-2, NAPLES

$4,300

7310 Salerno Ct, NAPLES

$4,300

4706 West Blvd W3, NAPLES

$4,250

480 Bermuda Cove Way 1-104, NAPLES

$4,250

6954 Avalon Cir 707, NAPLES

$4,250

3830 Sawgrass Way 2934, NAPLES

$4,250

4960 Deerfield Way E102, NAPLES

$4,250

3013 Futuna Ln, NAPLES

$4,200

3950 Loblolly Bay Dr 3-402, NAPLES

$4,200

6960 Avalon Cir 807, NAPLES

$4,200

7103 Lily Way, NAPLES

$4,200

1299 Verde Dr 1503, NAPLES

$4,200

1911 Morning Sun Lane, NAPLES

$4,200

1910 Gulf Shore Blvd N 112, NAPLES

$4,200

2050 W Crown Pointe Blvd C214, NAPLES

$4,200

613 Serendipity Dr 613, NAPLES

$4,200

3032 Woodside Ave, NAPLES