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

$12,000

648 96th Ave N, NAPLES

3 Beds 2 Baths 1,768 SqFt Rental MLS® # 226013354

Downing Frye Realty Inc.

$12,000

↑ $5,500

16903 Fairgrove Way 102, NAPLES

3 Beds 2 Baths 1,710 SqFt Rental MLS® # 226013123

Real Broker, LLC

$12,000

9491 Piacere Way, NAPLES

2 Beds 3 Baths 1,901 SqFt Rental MLS® # 226012970

WeichertRealtors-ParadiseHomes

$12,000

↓ $2,500

302 2nd St S 302, NAPLES

2 Beds 2 Baths 1,340 SqFt Rental MLS® # 226012879

Diversified Real Estate Group

$12,000

5550 Heron Point Dr 902, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 226012699

Royal Shell Real Estate, Inc.

$12,000

6105 Dogleg Dr, NAPLES

3 Beds 3 Baths 1,945 SqFt Rental MLS® # 226011952

Premier Sotheby's Int'l Realty

$12,000

760 106th Ave, NAPLES

3 Beds 2 Baths 1,968 SqFt Rental MLS® # 226009665

Gulf Breeze Real Estate LC

$12,000

↓ $1,000

9123 Strada Pl 7404, NAPLES

2 Beds 2 Baths 1,475 SqFt Rental MLS® # 226011508

Premier Sotheby's Int'l Realty

$12,000

5501 Heron Pt Dr 201, NAPLES

2 Beds 2 Baths 1,230 SqFt Rental MLS® # 226008947

William Raveis Real Estate

$12,000

776 Willowbrook Dr 804, NAPLES

2 Beds 2 Baths 1,701 SqFt Rental MLS® # 226011124

Douglas Elliman Florida,LLC

$12,000

6513 Caldecott Dr, NAPLES

3 Beds 2 Baths 2,125 SqFt Rental MLS® # 226009523

Premier Sotheby's Int'l Realty

$12,000

10691 Gulf Shore Dr E 1101, NAPLES

2 Beds 2 Baths 1,675 SqFt Rental MLS® # 2026008891

LPT Realty, LLC

$12,000

300 Dunes Blvd 603, NAPLES

3 Beds 2 Baths 1,893 SqFt Rental MLS® # 226008499

William Raveis Real Estate

$12,000

7831 Valencia Ct, NAPLES

3 Beds 2 Baths 1,936 SqFt Rental MLS® # 226007666

Downing Frye Realty Inc.

$12,000

6737 Bent Grass Dr, NAPLES

3 Beds 2 Baths 1,745 SqFt Rental MLS® # 226006888

Achieve Realty LLC

$12,000

3115 Gulf Shore Blvd N 412s, NAPLES

2 Beds 3 Baths 1,505 SqFt Rental MLS® # 226005523

John R Wood Properties

$12,000

10682 Gulf Shore Dr C-204, NAPLES

2 Beds 2 Baths 1,177 SqFt Rental MLS® # 226003893

John R Wood Properties

$12,000

5601 Turtle Bay Dr W 602, NAPLES

2 Beds 2 Baths 2,000 SqFt Rental MLS® # 226000361

Berkshire Hathaway FL Realty

$12,000

400 Flagship Dr 306, NAPLES

3 Beds 3 Baths 1,750 SqFt Rental MLS® # 226001581

William Raveis Real Estate

$12,000

410 Flagship Dr 1101, NAPLES

3 Beds 3 Baths 1,979 SqFt Rental MLS® # 225083250

William Raveis Real Estate

$12,000

↓ $3,000

1065 Borghese Ln 1503, NAPLES

3 Beds 3 Baths 1,865 SqFt Rental MLS® # 225081221

Century 21 AllPoints Realty

$12,000

↑ $4,000

3443 Gulf Shore Blvd N 814, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 225077717

Keller Williams Realty Naples

$12,000

↑ $2,000

92 Glen Eagle Cir, NAPLES

3 Beds 2 Baths 1,562 SqFt Rental MLS® # 225079133

Downing Frye Realty Inc.

$12,000

824 Tanbark Dr 204, NAPLES

3 Beds 2 Baths 1,481 SqFt Rental MLS® # 225077837

William Raveis Real Estate

$12,000

5550 Heron Point Dr 1802, NAPLES

2 Beds 2 Baths 1,263 SqFt Rental MLS® # 225074192

Premier Sotheby's Int'l Realty

$12,000

↑ $7,500

450 Bayfront Pl 4508, NAPLES

3 Beds 3 Baths 1,796 SqFt Rental MLS® # 225072212

Compass Florida LLC

$12,000

6971 Amen Corner Ct, NAPLES

3 Beds 2 Baths 1,749 SqFt Rental MLS® # 225071476

WeichertRealtors-ParadiseHomes

$12,000

790 Willowbrook Dr 305, NAPLES

2 Beds 2 Baths 1,582 SqFt Rental MLS® # 225070571

William Raveis Real Estate

$11,900

↓ $600

7672 Sussex Ct, NAPLES

4 Beds 2 Baths 2,293 SqFt Rental MLS® # 2026021533

Sellstate Max Performance

$11,700

7117 Pelican Bay Blvd 1202, NAPLES

2 Beds 2 Baths 1,700 SqFt Rental MLS® # 226021093

Premier Sotheby's Int'l Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$12,000

648 96th Ave N, NAPLES

$12,000

16903 Fairgrove Way 102, NAPLES

$12,000

9491 Piacere Way, NAPLES

$12,000

302 2nd St S 302, NAPLES

$12,000

5550 Heron Point Dr 902, NAPLES

$12,000

6105 Dogleg Dr, NAPLES

$12,000

760 106th Ave, NAPLES

$12,000

9123 Strada Pl 7404, NAPLES

$12,000

5501 Heron Pt Dr 201, NAPLES

$12,000

776 Willowbrook Dr 804, NAPLES

$12,000

6513 Caldecott Dr, NAPLES

$12,000

10691 Gulf Shore Dr E 1101, NAPLES

$12,000

300 Dunes Blvd 603, NAPLES

$12,000

7831 Valencia Ct, NAPLES

$12,000

6737 Bent Grass Dr, NAPLES

$12,000

3115 Gulf Shore Blvd N 412s, NAPLES

$12,000

10682 Gulf Shore Dr C-204, NAPLES

$12,000

5601 Turtle Bay Dr W 602, NAPLES

$12,000

400 Flagship Dr 306, NAPLES

$12,000

410 Flagship Dr 1101, NAPLES

$12,000

1065 Borghese Ln 1503, NAPLES

$12,000

3443 Gulf Shore Blvd N 814, NAPLES

$12,000

92 Glen Eagle Cir, NAPLES

$12,000

824 Tanbark Dr 204, NAPLES

$12,000

5550 Heron Point Dr 1802, NAPLES

$12,000

450 Bayfront Pl 4508, NAPLES

$12,000

6971 Amen Corner Ct, NAPLES

$12,000

790 Willowbrook Dr 305, NAPLES

$11,900

7672 Sussex Ct, NAPLES

$11,700

7117 Pelican Bay Blvd 1202, NAPLES