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

$11,500

7638 Pebble Creek Cir 4-202, NAPLES

2 Beds 2 Baths 1,327 SqFt Rental MLS® # 226027612

Premier Sotheby's Int'l Realty

$11,500

5878 Haiti Dr, NAPLES

2 Beds 2 Baths 1,563 SqFt Rental MLS® # 226026158

William Raveis Real Estate

$11,500

11116 Gulf Shore Dr 601, NAPLES

2 Beds 2 Baths 1,476 SqFt Rental MLS® # 226024945

Royal Shell Real Estate, Inc.

$11,500

400 Flagship Dr 505, NAPLES

3 Beds 3 Baths 1,760 SqFt Rental MLS® # 226018444

William Raveis Real Estate

$11,500

↓ $2,500

300 Dunes Blvd 107, NAPLES

3 Beds 3 Baths 2,200 SqFt Rental MLS® # 225079814

All In Property Management LLC

$11,500

↑ $1,000

837 Sailaway Ln 202, NAPLES

3 Beds 2 Baths 1,703 SqFt Rental MLS® # 225071595

Premier Sotheby's Int'l Realty

$11,500

↑ $1,000

2312 Island Cove Cir, NAPLES

3 Beds 3 Baths 2,900 SqFt Rental MLS® # 225072190

Premier Sotheby's Int'l Realty

$11,500

5901 Ashford Ln, NAPLES

4 Beds 4 Baths 3,200 SqFt Rental MLS® # 225069814

Royal Shell Real Estate, Inc.

$11,495

9103 Vanderbilt Dr 205, NAPLES

2 Beds 2 Baths 1,221 SqFt Rental MLS® # 226026028

Berkshire Hathaway FL Realty

$11,000

6560 Roma Way, NAPLES

3 Beds 2 Baths 2,188 SqFt Rental MLS® # 226030198

Premier Sotheby's Int'l Realty

$11,000

2438 Butterfly Palm Dr, NAPLES

3 Beds 2 Baths 1,996 SqFt Rental MLS® # 226030193

Premier Sotheby's Int'l Realty

$11,000

7563 Moorgate Point Way, NAPLES

3 Beds 2 Baths 1,924 SqFt Rental MLS® # 226029974

Berkshire Hathaway FL Realty

$11,000

400 Flagship Dr 505, NAPLES

3 Beds 3 Baths 1,760 SqFt Rental MLS® # 226029545

William Raveis Real Estate

$11,000

2500 Kings Lake Blvd, NAPLES

4 Beds 2 Baths 2,103 SqFt Rental MLS® # 226025129

Compass Florida LLC

$11,000

2728 Tiburon Blvd E A-203, NAPLES

2 Beds 2 Baths 1,465 SqFt Rental MLS® # 226023593

Berkshire Hathaway FL Realty

$11,000

1060 6th St S 1060, NAPLES

2 Beds 3 Baths 1,570 SqFt Rental MLS® # 226023437

Compass Florida LLC

$11,000

1031 Tivoli Ln, NAPLES

4 Beds 3 Baths 2,211 SqFt Rental MLS® # 226022579

Berkshire Hathaway FL Realty

$11,000

↓ $1,000

4451 Gulf Shore Blvd N 601, NAPLES

3 Beds 3 Baths 2,100 SqFt Rental MLS® # 226014012

Downing Frye Realty Inc.

$11,000

5501 Heron Point Dr 702, NAPLES

2 Beds 2 Baths 1,155 SqFt Rental MLS® # 226019036

William Raveis Real Estate

$11,000

1959 Dory Ct, NAPLES

3 Beds 3 Baths 1,640 SqFt Rental MLS® # 226017088

Royal Shell Real Estate, Inc.

$11,000

6080 Pelican Bay Blvd 104a, NAPLES

2 Beds 2 Baths 1,538 SqFt Rental MLS® # 226016575

Royal Shell Real Estate, Inc.

$11,000

8765 Bellano Ct 202, NAPLES

3 Beds 3 Baths 2,343 SqFt Rental MLS® # 226009716

Berkshire Hathaway FL Realty

$11,000

9101 Vanderbilt Dr 304, NAPLES

2 Beds 2 Baths 1,335 SqFt Rental MLS® # 226013157

SunStream Realty

$11,000

↑ $1,000

451 Bayfront Pl 5505, NAPLES

2 Beds 2 Baths 1,518 SqFt Rental MLS® # 226012740

Compass Florida LLC

$11,000

↑ $1,000

261 Colonade Cir 2701, NAPLES

2 Beds 3 Baths 1,991 SqFt Rental MLS® # 226006536

ALL IN PROPERTY MANAGEMENT LLC

$11,000

2147 Yellowfin Cir, NAPLES

4 Beds 3 Baths 2,615 SqFt Rental MLS® # 226002616

Coldwell Banker Realty

$11,000

7048 Pelican Bay Blvd C302, NAPLES

2 Beds 2 Baths 1,826 SqFt Rental MLS® # 226004012

John R Wood Properties

$11,000

↑ $500

634 Soliel Dr, NAPLES

3 Beds 3 Baths 3,142 SqFt Rental MLS® # 225084375

William Raveis Real Estate

$11,000

2396 Ravenna Blvd 102, NAPLES

3 Beds 2 Baths 1,619 SqFt Rental MLS® # 225084009

Real Estate Specialty Svcs II

$11,000

↑ $2,000

10682 Gulf Shore Dr C205, NAPLES

2 Beds 2 Baths 1,248 SqFt Rental MLS® # 225080651

John R Wood Properties

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$11,500

7638 Pebble Creek Cir 4-202, NAPLES

$11,500

5878 Haiti Dr, NAPLES

$11,500

11116 Gulf Shore Dr 601, NAPLES

$11,500

400 Flagship Dr 505, NAPLES

$11,500

300 Dunes Blvd 107, NAPLES

$11,500

837 Sailaway Ln 202, NAPLES

$11,500

2312 Island Cove Cir, NAPLES

$11,500

5901 Ashford Ln, NAPLES

$11,495

9103 Vanderbilt Dr 205, NAPLES

$11,000

6560 Roma Way, NAPLES

$11,000

2438 Butterfly Palm Dr, NAPLES

$11,000

7563 Moorgate Point Way, NAPLES

$11,000

400 Flagship Dr 505, NAPLES

$11,000

2500 Kings Lake Blvd, NAPLES

$11,000

2728 Tiburon Blvd E A-203, NAPLES

$11,000

1060 6th St S 1060, NAPLES

$11,000

1031 Tivoli Ln, NAPLES

$11,000

4451 Gulf Shore Blvd N 601, NAPLES

$11,000

5501 Heron Point Dr 702, NAPLES

$11,000

1959 Dory Ct, NAPLES

$11,000

6080 Pelican Bay Blvd 104a, NAPLES

$11,000

8765 Bellano Ct 202, NAPLES

$11,000

9101 Vanderbilt Dr 304, NAPLES

$11,000

451 Bayfront Pl 5505, NAPLES

$11,000

261 Colonade Cir 2701, NAPLES

$11,000

2147 Yellowfin Cir, NAPLES

$11,000

7048 Pelican Bay Blvd C302, NAPLES

$11,000

634 Soliel Dr, NAPLES

$11,000

2396 Ravenna Blvd 102, NAPLES

$11,000

10682 Gulf Shore Dr C205, NAPLES