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

$9,000

6559 Monterey Pt, NAPLES

3 Beds 2 Baths 2,300 SqFt Rental MLS® # 226002730

Waterfront Realty Group Inc

$9,000

1144 Egrets Walk Cir 202, NAPLES

3 Beds 2 Baths 1,800 SqFt Rental MLS® # 225083147

John R Wood Properties

$9,000

↑ $1,000

401 Bayfront Pl 3205, NAPLES

2 Beds 2 Baths 1,223 SqFt Rental MLS® # 225082312

Compass Florida LLC

$9,000

2750 Gulf Shore Blvd N 402, NAPLES

2 Beds 2 Baths 1,542 SqFt Rental MLS® # 225081048

William Raveis Real Estate

$9,000

450 Bayfront Pl 4206, NAPLES

1 Bed 2 Baths 1,356 SqFt Rental MLS® # 225072219

Compass Florida LLC

$9,000

8405 Excalibur Cir D3, NAPLES

2 Beds 2 Baths 1,382 SqFt Rental MLS® # 225074711

RE/MAX Hallmark Realty

$9,000

↓ $1,000

45 Wickliffe Dr, NAPLES

4 Beds 2 Baths 1,749 SqFt Rental MLS® # 225069829

Coldwell Banker Realty

$9,000

4200 Belair Ln 113, NAPLES

2 Beds 2 Baths 1,600 SqFt Rental MLS® # 225069809

Royal Shell Real Estate, Inc.

$9,000

↑ $1,000

784 Willowbrook Dr 608, NAPLES

2 Beds 2 Baths 1,582 SqFt Rental MLS® # 225069807

Royal Shell Real Estate, Inc.

$9,000

982 Tivoli Ct, NAPLES

3 Beds 3 Baths 2,281 SqFt Rental MLS® # 225069751

Posh International Properties

$8,995

↑ $1,000

410 Bayfront Pl 2307, NAPLES

2 Beds 2 Baths 1,344 SqFt Rental MLS® # 226022866

John R Wood Properties

$8,900

4180 Crayton Rd E7, NAPLES

3 Beds 2 Baths 1,600 SqFt Rental MLS® # 225084836

Achieve Realty LLC

New New

$8,800

6478 Waverly Green Way, NAPLES

3 Beds 3 Baths 1,711 SqFt Rental MLS® # 226031415

Woodruff Property Management

$8,800

100 Lambiance Cir 1-101, NAPLES

2 Beds 2 Baths 1,389 SqFt Rental MLS® # 226016243

Downing Frye Realty Inc.

$8,800

↓ $79,200

6478 Waverly Green Way, NAPLES

3 Beds 3 Baths 1,711 SqFt Rental MLS® # 225074323

Woodruff Property Management

$8,700

335 Lambton Ln, NAPLES

4 Beds 3 Baths 2,367 SqFt Rental MLS® # 226027824

William Raveis Real Estate

$8,700

9533 Avellino Way 2916, NAPLES

2 Beds 2 Baths 1,661 SqFt Rental MLS® # 226015037

William Raveis Real Estate

$8,700

2383 Ravenna Blvd Ph 202, NAPLES

3 Beds 3 Baths 2,100 SqFt Rental MLS® # 226014392

Real Estate Specialty Svcs II

$8,700

↓ $800

13466 Sumter Ln, NAPLES

3 Beds 2 Baths 1,837 SqFt Rental MLS® # 225072657

John R Wood Properties

$8,500

2717 Callista Ct 104, NAPLES

3 Beds 3 Baths 2,502 SqFt Rental MLS® # 226029724

Premier Sotheby's Int'l Realty

$8,500

6413 Legacy Cir 1602, NAPLES

2 Beds 2 Baths 2,160 SqFt Rental MLS® # 226028549

John R Wood Properties

$8,500

300 L Ambiance Cir 102, NAPLES

2 Beds 2 Baths 1,618 SqFt Rental MLS® # 226023546

Downing Frye Realty Inc.

$8,500

2728 Tiburon Blvd E A204, NAPLES

2 Beds 2 Baths 1,470 SqFt Rental MLS® # 226025143

William Raveis Real Estate

$8,500

832 Tanbark Dr 104, NAPLES

2 Beds 2 Baths 1,203 SqFt Rental MLS® # 226024458

William Raveis Real Estate

$8,500

12832 Brynwood Way, NAPLES

3 Beds 2 Baths 1,714 SqFt Rental MLS® # 226027334

Realty One Group MVP

$8,500

3400 Gulf Shore Blvd N B2, NAPLES

2 Beds 2 Baths 1,450 SqFt Rental MLS® # 226023495

William Raveis Real Estate

$8,500

9123 Strada Pl 7307, NAPLES

1 Bed 2 Baths 1,484 SqFt Rental MLS® # 226024720

Premier Sotheby's Int'l Realty

$8,500

8013 Calle Canovas Ct, NAPLES

2 Beds 2 Baths 1,552 SqFt Rental MLS® # 226024188

Berkshire Hathaway FL Realty

$8,500

↑ $1,000

2868 Tiburon Blvd E 102, NAPLES

3 Beds 2 Baths 2,450 SqFt Rental MLS® # 226022487

Royal Shell Real Estate, Inc.

$8,500

772 Reef Point Cir 55, NAPLES

3 Beds 2 Baths 1,604 SqFt Rental MLS® # 226022225

Realty One Group MVP

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$9,000

6559 Monterey Pt, NAPLES

$9,000

1144 Egrets Walk Cir 202, NAPLES

$9,000

401 Bayfront Pl 3205, NAPLES

$9,000

2750 Gulf Shore Blvd N 402, NAPLES

$9,000

450 Bayfront Pl 4206, NAPLES

$9,000

8405 Excalibur Cir D3, NAPLES

$9,000

45 Wickliffe Dr, NAPLES

$9,000

4200 Belair Ln 113, NAPLES

$9,000

784 Willowbrook Dr 608, NAPLES

$9,000

982 Tivoli Ct, NAPLES

$8,995

410 Bayfront Pl 2307, NAPLES

$8,900

4180 Crayton Rd E7, NAPLES

$8,800

6478 Waverly Green Way, NAPLES

$8,800

100 Lambiance Cir 1-101, NAPLES

$8,800

6478 Waverly Green Way, NAPLES

$8,700

335 Lambton Ln, NAPLES

$8,700

9533 Avellino Way 2916, NAPLES

$8,700

2383 Ravenna Blvd Ph 202, NAPLES

$8,700

13466 Sumter Ln, NAPLES

$8,500

2717 Callista Ct 104, NAPLES

$8,500

6413 Legacy Cir 1602, NAPLES

$8,500

300 L Ambiance Cir 102, NAPLES

$8,500

2728 Tiburon Blvd E A204, NAPLES

$8,500

832 Tanbark Dr 104, NAPLES

$8,500

12832 Brynwood Way, NAPLES

$8,500

3400 Gulf Shore Blvd N B2, NAPLES

$8,500

9123 Strada Pl 7307, NAPLES

$8,500

8013 Calle Canovas Ct, NAPLES

$8,500

2868 Tiburon Blvd E 102, NAPLES

$8,500

772 Reef Point Cir 55, NAPLES