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

$11,000

271 Broad Ave S 203, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225080625

Coldwell Banker Realty

$11,000

6525 Valen Way D-302, NAPLES

3 Beds 2 Baths 1,233 SqFt Rental MLS® # 225077835

William Raveis Real Estate

$11,000

5899 Chanteclair Dr 226, NAPLES

3 Beds 2 Baths 1,506 SqFt Rental MLS® # 225077831

William Raveis Real Estate

$11,000

↑ $5,500

N/A, NAPLES

3 Beds 2 Baths 1,633 SqFt Rental MLS® # 225072227

Compass Florida LLC

$11,000

↓ $3,000

1507 Vintage Ln, NAPLES

3 Beds 2 Baths 1,874 SqFt Rental MLS® # 225071145

Waterfront Realty Group Inc

$11,000

4001 Gulf Shore Blvd N 1104, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 225072111

Premier Sotheby's Int'l Realty

$10,975

1035 3rd Ave S 303, NAPLES

2 Beds 2 Baths 1,268 SqFt Rental MLS® # 225069813

Royal Shell Real Estate, Inc.

$10,850

9727 Acqua Ct 418, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226018069

eXp Realty LLC

$10,800

↓ $1,000

282 4th St S, NAPLES

2 Beds 2 Baths 1,058 SqFt Rental MLS® # 225084222

ALL IN PROPERTY MANAGEMENT LLC

$10,700

7932 Princeton Dr, NAPLES

3 Beds 3 Baths 2,185 SqFt Rental MLS® # 226015008

Royal Shell Real Estate, Inc.

New New

$10,500

793 97th Ave N, NAPLES

3 Beds 2 Baths 1,700 SqFt Rental MLS® # 226030902

Royal Shell Real Estate, Inc.

$10,500

3443 Gulf Shore Blvd N 609, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 226030526

DomainRealty.com LLC

$10,500

564 107th Ave N, NAPLES

3 Beds 2 Baths 1,800 SqFt Rental MLS® # 226028567

Downing Frye Realty Inc.

$10,500

7050 Barrington Cir 201, NAPLES

2 Beds 2 Baths 1,527 SqFt Rental MLS® # 226027609

Premier Sotheby's Int'l Realty

$10,500

1540 Clermont Dr F403, NAPLES

3 Beds 2 Baths 1,926 SqFt Rental MLS® # 226024475

My Florida Real Estate, LLC

$10,500

6585 Nicholas Blvd 805, NAPLES

3 Beds 2 Baths 1,799 SqFt Rental MLS® # 226023528

Premier Sotheby's Int'l Realty

$10,500

↑ $10,000

693 105th Ave N, NAPLES

4 Beds 3 Baths 2,014 SqFt Rental MLS® # 2026022992

Realty Group of SW Florida Inc

$10,500

325 Dunes Blvd 406, NAPLES

3 Beds 3 Baths 2,194 SqFt Rental MLS® # 226018443

William Raveis Real Estate

$10,500

285 5th Ave S 2b, NAPLES

2 Beds 2 Baths 1,568 SqFt Rental MLS® # 226009654

Sun Realty

$10,500

6604 Roma Way, NAPLES

3 Beds 2 Baths 2,114 SqFt Rental MLS® # 225079523

Waterfront Realty Group Inc

$10,500

7040 Pelican Bay Blvd D404, NAPLES

2 Beds 2 Baths 1,607 SqFt Rental MLS® # 225077138

Royal Shell Real Estate, Inc.

$10,500

↑ $3,500

300 Wentworth Ct, NAPLES

3 Beds 3 Baths 2,626 SqFt Rental MLS® # 225073689

Waterfront Realty Group Inc

$10,479

↑ $2,979

1295 Gulf Shore Blvd S 218, NAPLES

2 Beds 2 Baths 662 SqFt Rental MLS® # 226010595

John R Wood Properties

New New

$10,000

8051 Players Cove Dr 102, NAPLES

3 Beds 3 Baths 2,091 SqFt Rental MLS® # 226030863

Downing Frye Realty Inc.

$10,000

2121 Gulfshore Blvd N 503, NAPLES

2 Beds 2 Baths 905 SqFt Rental MLS® # 226015164

Naples Vibe Realty, LLC

$10,000

↑ $9,000

280 4th St S 104, NAPLES

2 Beds 2 Baths 1,058 SqFt Rental MLS® # 226030277

John R Wood Properties

$10,000

6515 Valen Way H101, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 226028183

William Raveis Real Estate

$10,000

6839 Ascot Dr 202, NAPLES

3 Beds 2 Baths 2,040 SqFt Rental MLS® # 226029527

Berkshire Hathaway FL Realty

$10,000

6821 Ascot Dr 202, NAPLES

3 Beds 2 Baths 2,040 SqFt Rental MLS® # 226029526

Berkshire Hathaway FL Realty

$10,000

1100 Gulf Shore Blvd N 108, NAPLES

2 Beds 2 Baths 940 SqFt Rental MLS® # 226029444

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$11,000

271 Broad Ave S 203, NAPLES

$11,000

6525 Valen Way D-302, NAPLES

$11,000

5899 Chanteclair Dr 226, NAPLES

$11,000

N/A, NAPLES

$11,000

1507 Vintage Ln, NAPLES

$11,000

4001 Gulf Shore Blvd N 1104, NAPLES

$10,975

1035 3rd Ave S 303, NAPLES

$10,850

9727 Acqua Ct 418, NAPLES

$10,800

282 4th St S, NAPLES

$10,700

7932 Princeton Dr, NAPLES

$10,500

793 97th Ave N, NAPLES

$10,500

3443 Gulf Shore Blvd N 609, NAPLES

$10,500

564 107th Ave N, NAPLES

$10,500

7050 Barrington Cir 201, NAPLES

$10,500

1540 Clermont Dr F403, NAPLES

$10,500

6585 Nicholas Blvd 805, NAPLES

$10,500

693 105th Ave N, NAPLES

$10,500

325 Dunes Blvd 406, NAPLES

$10,500

285 5th Ave S 2b, NAPLES

$10,500

6604 Roma Way, NAPLES

$10,500

7040 Pelican Bay Blvd D404, NAPLES

$10,500

300 Wentworth Ct, NAPLES

$10,479

1295 Gulf Shore Blvd S 218, NAPLES

$10,000

8051 Players Cove Dr 102, NAPLES

$10,000

2121 Gulfshore Blvd N 503, NAPLES

$10,000

280 4th St S 104, NAPLES

$10,000

6515 Valen Way H101, NAPLES

$10,000

6839 Ascot Dr 202, NAPLES

$10,000

6821 Ascot Dr 202, NAPLES

$10,000

1100 Gulf Shore Blvd N 108, NAPLES