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

New New

$18,000

2605 Estrella Ct Ph-3, NAPLES

3 Beds 2 Baths 2,450 SqFt Rental MLS® # 226030865

Real Estate Specialty Svcs II

$18,000

223 11th Ave S, NAPLES

4 Beds 4 Baths 2,691 SqFt Rental MLS® # 226030118

John R Wood Properties

$18,000

4251 Gulf Shore Blvd N 6d, NAPLES

2 Beds 3 Baths 2,562 SqFt Rental MLS® # 226028595

Premier Sotheby's Int'l Realty

$18,000

6075 Pelican Bay Blvd 1101, NAPLES

2 Beds 3 Baths 2,264 SqFt Rental MLS® # 226028859

William Raveis Real Estate

$18,000

2851 Tiburon Blvd E 9-103, NAPLES

3 Beds 2 Baths 2,502 SqFt Rental MLS® # 226018189

William Raveis Real Estate

$18,000

548 101st Ave, NAPLES

4 Beds 3 Baths 2,208 SqFt Rental MLS® # 226028695

Gulf Breeze Real Estate LC

$18,000

10620 Gulf Shore Dr 201, NAPLES

3 Beds 4 Baths 2,357 SqFt Rental MLS® # 226028634

WeichertRealtors-ParadiseHomes

$18,000

4401 Gulf Shore Blvd N E-908, NAPLES

2 Beds 2 Baths 1,850 SqFt Rental MLS® # 226027608

Premier Sotheby's Int'l Realty

$18,000

7117 Pelican Bay Blvd 1508, NAPLES

2 Beds 2 Baths 1,697 SqFt Rental MLS® # 226022923

Premier Sotheby's Int'l Realty

$18,000

4041 Gulf Shore Blvd N 1109, NAPLES

2 Beds 3 Baths 2,240 SqFt Rental MLS® # 226024473

Hamro & Associates LLC

$18,000

16364 Viansa Way 202, NAPLES

3 Beds 4 Baths 2,350 SqFt Rental MLS® # 226021912

Real Broker, LLC

$18,000

1130 3rd Ave S 309, NAPLES

3 Beds 4 Baths 2,898 SqFt Rental MLS® # 226023814

Downing Frye Realty Inc.

$18,000

3254 Lakeview Dr, NAPLES

3 Beds 2 Baths 1,627 SqFt Rental MLS® # 226022310

John R Wood Properties

$18,000

↓ $2,000

2357 Gulf Shore Blvd N 107, NAPLES

2 Beds 3 Baths 1,663 SqFt Rental MLS® # 226022403

REMAX Affinity Mercato

$18,000

4031 Gulf Shore Blvd N 7d, NAPLES

3 Beds 3 Baths 2,500 SqFt Rental MLS® # 226015035

William Raveis Real Estate

$18,000

2625 Estrella Ct 15-1, NAPLES

3 Beds 2 Baths 1,768 SqFt Rental MLS® # 226009927

John R Wood Properties

$18,000

↑ $16,200

173 Palmetto Dunes Cir, NAPLES

4 Beds 3 Baths 2,890 SqFt Rental MLS® # 226009431

eXp Realty LLC

$18,000

837 99th Ave N, NAPLES

4 Beds 3 Baths 2,100 SqFt Rental MLS® # 226014854

Naples Vacation Properties

$18,000

↑ $3,000

10475 Gulf Shore Dr 165, NAPLES

3 Beds 2 Baths 1,594 SqFt Rental MLS® # 226011010

Paradise Lifestyles LLC

$18,000

410 Flagship 1104, NAPLES

3 Beds 4 Baths 2,320 SqFt Rental MLS® # 226009241

William Raveis Real Estate

$18,000

433 2nd St S B-202, NAPLES

3 Beds 3 Baths 1,667 SqFt Rental MLS® # 226006846

Coldwell Banker Realty

$18,000

↑ $3,000

2809 Tiburon Blvd E 2, NAPLES

3 Beds 2 Baths 2,159 SqFt Rental MLS® # 225084056

William Raveis Real Estate

$18,000

↓ $2,000

1020 Tivoli Ln, NAPLES

4 Beds 3 Baths 2,273 SqFt Rental MLS® # 225083342

Waterfront Realty Group Inc

$18,000

↓ $1,000

10701 Gulf Shore Dr 502, NAPLES

2 Beds 2 Baths 1,642 SqFt Rental MLS® # 225081577

Premier Sotheby's Int'l Realty

$18,000

428 9th St S, NAPLES

3 Beds 4 Baths 4,101 SqFt Rental MLS® # 225080623

Coldwell Banker Realty

$18,000

850 Central Ave 305, NAPLES

2 Beds 2 Baths 1,577 SqFt Rental MLS® # 225075922

Coldwell Banker Realty

$18,000

↓ $4,000

1130 3rd Ave S 215, NAPLES

3 Beds 4 Baths 2,733 SqFt Rental MLS® # 225075423

William Raveis Real Estate

$18,000

723 Willowhead Dr, NAPLES

3 Beds 3 Baths 1,776 SqFt Rental MLS® # 225073907

Coldwell Banker Realty

$18,000

↑ $1,000

6001 Pelican Bay Blvd 505, NAPLES

3 Beds 3 Baths 2,584 SqFt Rental MLS® # 225070712

Downing Frye Realty Inc.

$17,900

↓ $2,100

1600 Curlew Ave, NAPLES

3 Beds 2 Baths 1,817 SqFt Rental MLS® # 226010107

Troy Companies of Florida

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$18,000

2605 Estrella Ct Ph-3, NAPLES

$18,000

223 11th Ave S, NAPLES

$18,000

4251 Gulf Shore Blvd N 6d, NAPLES

$18,000

6075 Pelican Bay Blvd 1101, NAPLES

$18,000

2851 Tiburon Blvd E 9-103, NAPLES

$18,000

548 101st Ave, NAPLES

$18,000

10620 Gulf Shore Dr 201, NAPLES

$18,000

4401 Gulf Shore Blvd N E-908, NAPLES

$18,000

7117 Pelican Bay Blvd 1508, NAPLES

$18,000

4041 Gulf Shore Blvd N 1109, NAPLES

$18,000

16364 Viansa Way 202, NAPLES

$18,000

1130 3rd Ave S 309, NAPLES

$18,000

3254 Lakeview Dr, NAPLES

$18,000

2357 Gulf Shore Blvd N 107, NAPLES

$18,000

4031 Gulf Shore Blvd N 7d, NAPLES

$18,000

2625 Estrella Ct 15-1, NAPLES

$18,000

173 Palmetto Dunes Cir, NAPLES

$18,000

837 99th Ave N, NAPLES

$18,000

10475 Gulf Shore Dr 165, NAPLES

$18,000

410 Flagship 1104, NAPLES

$18,000

433 2nd St S B-202, NAPLES

$18,000

2809 Tiburon Blvd E 2, NAPLES

$18,000

1020 Tivoli Ln, NAPLES

$18,000

10701 Gulf Shore Dr 502, NAPLES

$18,000

428 9th St S, NAPLES

$18,000

850 Central Ave 305, NAPLES

$18,000

1130 3rd Ave S 215, NAPLES

$18,000

723 Willowhead Dr, NAPLES

$18,000

6001 Pelican Bay Blvd 505, NAPLES

$17,900

1600 Curlew Ave, NAPLES