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

$3,500

1055 Forest Lakes Dr E209, NAPLES

2 Beds 2 Baths 1,050 SqFt Rental MLS® # 226004026

Berkshire Hathaway FL Realty

$3,500

↓ $250

749 105th Ave N, NAPLES

3 Beds 2 Baths 1,394 SqFt Rental MLS® # 225084243

Naples Trust Real Estate Servi

$3,500

815 Gulf Pavilion Dr 203, NAPLES

2 Beds 2 Baths 1,179 SqFt Rental MLS® # 226002844

Century 21 AllPoints Realty

$3,500

800 Golf Dr S 104, NAPLES

2 Beds 2 Baths 1,060 SqFt Rental MLS® # 226029468

Andrea Deane & Associates, Inc

$3,500

12945 Vanderbilt Dr 402, NAPLES

2 Beds 2 Baths 1,102 SqFt Rental MLS® # 226011659

Florida Home Realty, Inc.

$3,500

↑ $1,500

321 Robin Hood Cir 201, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225075686

WeichertRealtors-ParadiseHomes

$3,500

9107 Napoli Ct 201, NAPLES

3 Beds 2 Baths 2,099 SqFt Rental MLS® # 226012302

WeichertRealtors-ParadiseHomes

$3,500

1405 Tiffany Ln 1408, NAPLES

2 Beds 2 Baths 1,795 SqFt Rental MLS® # 226013848

Coldwell Banker Realty

$3,500

9426 Benvenuto Ct 203, NAPLES

2 Beds 2 Baths 1,660 SqFt Rental MLS® # 226022633

Advantage Sales Of South FL

$3,500

4410 Chantelle Dr H-205, NAPLES

2 Beds 2 Baths 1,349 SqFt Rental MLS® # 226015006

Realty One Group MVP

$3,500

470 Launch Cir V301, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226018437

William Raveis Real Estate

$3,500

3019 Ellice Way, NAPLES

3 Beds 3 Baths 2,181 SqFt Rental MLS® # 226021143

Florida Home Realty, Inc.

$3,500

7895 Sanctuary Cir 117-1, NAPLES

3 Beds 2 Baths 1,742 SqFt Rental MLS® # 226019799

EXIT Realty of Naples

$3,500

3400 Frosty Way 5, NAPLES

2 Beds 2 Baths 1,284 SqFt Rental MLS® # 225077856

Bluewater Signature Realty LLC

$3,500

14864 Indigo Lakes Cir, NAPLES

3 Beds 2 Baths 1,934 SqFt Rental MLS® # 226027777

Alpizar & Company, LLC

$3,500

5 Bluebill Ave 205, NAPLES

0 Beds 1 Bath 500 SqFt Rental MLS® # 226006041

William Raveis Real Estate

$3,500

15145 Palmer Lake Cir 103, NAPLES

3 Beds 2 Baths 1,571 SqFt Rental MLS® # 226029609

Premier Sotheby's Int'l Realty

$3,500

9719 Acqua Ct 228, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226013390

WeichertRealtors-ParadiseHomes

$3,500

↓ $300

4584 Centaurus Cir, NAPLES

3 Beds 2 Baths 1,860 SqFt Rental MLS® # 226012962

Realty One Group MVP

$3,500

3320 Olympic Dr 125, NAPLES

2 Beds 2 Baths 965 SqFt Rental MLS® # 225070655

Realty One Group MVP

$3,495

2469 Millcreek Ln 102, NAPLES

2 Beds 2 Baths 1,107 SqFt Rental MLS® # 226000668

William Raveis Real Estate

$3,495

↓ $5

1313 Solana Rd W A3, NAPLES

2 Beds 2 Baths 1,728 SqFt Rental MLS® # 226003387

Downing Frye Realty Inc.

$3,495

332 Charlemagne Blvd H103, NAPLES

2 Beds 2 Baths 1,082 SqFt Rental MLS® # 225074174

Berkshire Hathaway FL Realty

$3,450

↓ $200

3618 Arctic Cir 3618, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 225069691

Gulf Region Realty

$3,400

1195 Wildwood Lakes Blvd 202, NAPLES

2 Beds 1 Bath 909 SqFt Rental MLS® # 225069134

Realty One Group MVP

$3,400

3964 Bishopwood Ct E 1-202, NAPLES

2 Beds 2 Baths 1,417 SqFt Rental MLS® # 226021894

Premier Property Management

$3,400

1820 Florida Club Cir 2210, NAPLES

3 Beds 2 Baths 1,189 SqFt Rental MLS® # 225076002

Starlink Realty, Inc

$3,400

400 Forest Lakes Blvd 309, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226021066

Downing Frye Realty Inc.

$3,300

208 Bob O Link Way B, NAPLES

3 Beds 2 Baths 1,660 SqFt Rental MLS® # 226028880

Century 21 AllPoints Realty

$3,300

7345 Rockefeller Dr, NAPLES

3 Beds 3 Baths 1,868 SqFt Rental MLS® # 226022721

Berkshire Hathaway FL Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$3,500

1055 Forest Lakes Dr E209, NAPLES

$3,500

749 105th Ave N, NAPLES

$3,500

815 Gulf Pavilion Dr 203, NAPLES

$3,500

800 Golf Dr S 104, NAPLES

$3,500

12945 Vanderbilt Dr 402, NAPLES

$3,500

321 Robin Hood Cir 201, NAPLES

$3,500

9107 Napoli Ct 201, NAPLES

$3,500

1405 Tiffany Ln 1408, NAPLES

$3,500

9426 Benvenuto Ct 203, NAPLES

$3,500

4410 Chantelle Dr H-205, NAPLES

$3,500

470 Launch Cir V301, NAPLES

$3,500

3019 Ellice Way, NAPLES

$3,500

7895 Sanctuary Cir 117-1, NAPLES

$3,500

3400 Frosty Way 5, NAPLES

$3,500

14864 Indigo Lakes Cir, NAPLES

$3,500

5 Bluebill Ave 205, NAPLES

$3,500

15145 Palmer Lake Cir 103, NAPLES

$3,500

9719 Acqua Ct 228, NAPLES

$3,500

4584 Centaurus Cir, NAPLES

$3,500

3320 Olympic Dr 125, NAPLES

$3,495

2469 Millcreek Ln 102, NAPLES

$3,495

1313 Solana Rd W A3, NAPLES

$3,495

332 Charlemagne Blvd H103, NAPLES

$3,450

3618 Arctic Cir 3618, NAPLES

$3,400

1195 Wildwood Lakes Blvd 202, NAPLES

$3,400

3964 Bishopwood Ct E 1-202, NAPLES

$3,400

1820 Florida Club Cir 2210, NAPLES

$3,400

400 Forest Lakes Blvd 309, NAPLES

$3,300

208 Bob O Link Way B, NAPLES

$3,300

7345 Rockefeller Dr, NAPLES