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

$25,000

2751 Tiburon Blvd E 201, NAPLES

3 Beds 4 Baths 2,930 SqFt Rental MLS® # 225066892

William Raveis Real Estate

$24,000

4041 Gulf Shore Blvd N Ph5, NAPLES

3 Beds 3 Baths 2,520 SqFt Rental MLS® # 226027869

William Raveis Real Estate

$24,000

517 Parkwood Ln, NAPLES

3 Beds 3 Baths 2,831 SqFt Rental MLS® # 226027257

William Raveis Real Estate

$24,000

2659 Bolero Dr 3, NAPLES

3 Beds 2 Baths 2,341 SqFt Rental MLS® # 226002436

Coldwell Banker Realty

$24,000

8990 Bay Colony Dr 1203, NAPLES

2 Beds 3 Baths 2,610 SqFt Rental MLS® # 225084711

Royal Shell Real Estate, Inc.

$24,000

201 8th St S 209, NAPLES

2 Beds 3 Baths 1,704 SqFt Rental MLS® # 225082885

John R Wood Properties

$24,000

↑ $1,500

2630 Bolero Dr 2-3, NAPLES

3 Beds 2 Baths 2,256 SqFt Rental MLS® # 225071787

William Raveis Real Estate

$24,000

150 1st Ave N, NAPLES

3 Beds 2 Baths 2,097 SqFt Rental MLS® # 225069290

John R Wood Properties

$23,600

605 6th Ave N, NAPLES

3 Beds 3 Baths 2,300 SqFt Rental MLS® # 226005283

Luxury Real Estate LLC

$23,500

↓ $500

383 Seabee Ave, NAPLES

3 Beds 2 Baths 1,923 SqFt Rental MLS® # 226028517

Gulf Breeze Real Estate LC

$23,500

2547 Marquesa Royale Ln 3-201, NAPLES

3 Beds 4 Baths 2,917 SqFt Rental MLS® # 226013126

Berkshire Hathaway FL Realty

$23,000

675 Harbour Dr, NAPLES

4 Beds 3 Baths 2,693 SqFt Rental MLS® # 226026988

Premier Sotheby's Int'l Realty

$23,000

275 Indies Way 1205, NAPLES

3 Beds 3 Baths 2,798 SqFt Rental MLS® # 226018761

William Raveis Real Estate

$23,000

275 Indies Way 706, NAPLES

3 Beds 3 Baths 2,893 SqFt Rental MLS® # 226016125

William Raveis Real Estate

$23,000

↓ $2,000

433 Crestwood Ln, NAPLES

3 Beds 4 Baths 3,533 SqFt Rental MLS® # 226012321

Premier Sotheby's Int'l Realty

$23,000

734 109th Ave N, NAPLES

5 Beds 3 Baths 2,208 SqFt Rental MLS® # 225082100

Sun Realty

$22,500

↓ $1,500

9653 Gulf Shore Dr 203, NAPLES

3 Beds 3 Baths 2,010 SqFt Rental MLS® # 226026989

Premier Sotheby's Int'l Realty

$22,500

4251 Gulf Shore Blvd N 17a, NAPLES

2 Beds 2 Baths 2,101 SqFt Rental MLS® # 226019772

Royal Shell Real Estate, Inc.

$22,500

265 Indies Way T1, NAPLES

3 Beds 4 Baths 2,893 SqFt Rental MLS® # 226016123

William Raveis Real Estate

New New

$22,000

1165 4th St S 2, NAPLES

3 Beds 4 Baths 2,100 SqFt Rental MLS® # 226031005

Royal Shell Real Estate, Inc.

New New

$22,000

3130 Heather Glen Ct, NAPLES

4 Beds 3 Baths 2,725 SqFt Rental MLS® # 226030911

Premier Sotheby's Int'l Realty

$22,000

343 Conners Ave, NAPLES

3 Beds 2 Baths 2,014 SqFt Rental MLS® # 226028710

Gulf Breeze Real Estate LC

$22,000

4451 Gulf Shore Blvd N 1604, NAPLES

3 Beds 2 Baths 2,250 SqFt Rental MLS® # 226023379

Coldwell Banker Realty

$22,000

10620 Gulf Shore Dr 602, NAPLES

3 Beds 4 Baths 3,252 SqFt Rental MLS® # 226022617

Premier Sotheby's Int'l Realty

$22,000

265 Indies Way 904, NAPLES

3 Beds 3 Baths 2,798 SqFt Rental MLS® # 226019656

William Raveis Real Estate

$22,000

572 11th Ave S 2, NAPLES

3 Beds 4 Baths 2,520 SqFt Rental MLS® # 226009571

John R Wood Properties

$22,000

4651 Gulf Shore Blvd N 504, NAPLES

2 Beds 3 Baths 2,000 SqFt Rental MLS® # 226006636

Royal Shell Real Estate, Inc.

$22,000

2728 Tiburon Blvd E 302, NAPLES

3 Beds 4 Baths 2,325 SqFt Rental MLS® # 225071785

William Raveis Real Estate

$21,500

↓ $500

9234 Veneto Pl, NAPLES

3 Beds 3 Baths 2,032 SqFt Rental MLS® # 226007304

Downing Frye Realty Inc.

$21,500

4651 Gulf Shore Blvd N 901, NAPLES

2 Beds 2 Baths 1,862 SqFt Rental MLS® # 225082988

Douglas Elliman Florida,LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$25,000

2751 Tiburon Blvd E 201, NAPLES

$24,000

4041 Gulf Shore Blvd N Ph5, NAPLES

$24,000

517 Parkwood Ln, NAPLES

$24,000

2659 Bolero Dr 3, NAPLES

$24,000

8990 Bay Colony Dr 1203, NAPLES

$24,000

201 8th St S 209, NAPLES

$24,000

2630 Bolero Dr 2-3, NAPLES

$24,000

150 1st Ave N, NAPLES

$23,600

605 6th Ave N, NAPLES

$23,500

383 Seabee Ave, NAPLES

$23,500

2547 Marquesa Royale Ln 3-201, NAPLES

$23,000

675 Harbour Dr, NAPLES

$23,000

275 Indies Way 1205, NAPLES

$23,000

275 Indies Way 706, NAPLES

$23,000

433 Crestwood Ln, NAPLES

$23,000

734 109th Ave N, NAPLES

$22,500

9653 Gulf Shore Dr 203, NAPLES

$22,500

4251 Gulf Shore Blvd N 17a, NAPLES

$22,500

265 Indies Way T1, NAPLES

$22,000

1165 4th St S 2, NAPLES

$22,000

3130 Heather Glen Ct, NAPLES

$22,000

343 Conners Ave, NAPLES

$22,000

4451 Gulf Shore Blvd N 1604, NAPLES

$22,000

10620 Gulf Shore Dr 602, NAPLES

$22,000

265 Indies Way 904, NAPLES

$22,000

572 11th Ave S 2, NAPLES

$22,000

4651 Gulf Shore Blvd N 504, NAPLES

$22,000

2728 Tiburon Blvd E 302, NAPLES

$21,500

9234 Veneto Pl, NAPLES

$21,500

4651 Gulf Shore Blvd N 901, NAPLES