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

$5,900

141 Bristol Ln C-21, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225070448

Real Estate Specialty Svcs II

$5,800

1417 Chesapeake Ave 104, NAPLES

2 Beds 2 Baths 913 SqFt Rental MLS® # 226029035

Downing Frye Realty Inc.

$5,800

7345 Rockefeller Dr, NAPLES

3 Beds 3 Baths 1,868 SqFt Rental MLS® # 226019959

Berkshire Hathaway FL Realty

$5,800

6900 Dennis Cir J-205, NAPLES

2 Beds 2 Baths 1,900 SqFt Rental MLS® # 226017311

Premier Sotheby's Int'l Realty

$5,800

9022 Michael Cir 4, NAPLES

2 Beds 2 Baths 1,619 SqFt Rental MLS® # 226006804

Premier Sotheby's Int'l Realty

$5,800

9419 Benvenuto Ct 204, NAPLES

2 Beds 2 Baths 1,632 SqFt Rental MLS® # 225070175

Posh International Properties

$5,795

3985 Deer Crossing Ct 201, NAPLES

3 Beds 2 Baths 1,981 SqFt Rental MLS® # 226018997

Premier Property Management

$5,750

2604 Sailors Way 120, NAPLES

2 Beds 2 Baths 1,429 SqFt Rental MLS® # 226026866

Downing Frye Realty Inc.

$5,750

2190 Arielle Dr 902, NAPLES

2 Beds 2 Baths 1,800 SqFt Rental MLS® # 226011734

DomainRealty.com LLC

$5,750

↓ $250

500 Misty Pines Cir 206, NAPLES

2 Beds 2 Baths 1,260 SqFt Rental MLS® # 226016548

Premier Sotheby's Int'l Realty

$5,750

7828 Gardner Dr 5-202, NAPLES

3 Beds 2 Baths 1,960 SqFt Rental MLS® # 225079935

Downing Frye Realty Inc.

$5,700

9088 Chula Vista St 108-3, NAPLES

2 Beds 2 Baths 1,404 SqFt Rental MLS® # 226012638

Premier Sotheby's Int'l Realty

$5,650

5125 Cedar Springs Dr 204, NAPLES

3 Beds 2 Baths 2,177 SqFt Rental MLS® # 226014073

Downing Frye Realty Inc.

$5,600

3048 Horizon Ln 1103, NAPLES

2 Beds 2 Baths 1,482 SqFt Rental MLS® # 226026984

Marzucco Real Estate

$5,600

640 Luisa Ln 804-4, NAPLES

3 Beds 2 Baths 1,639 SqFt Rental MLS® # 226022892

Premier Sotheby's Int'l Realty

$5,550

↓ $150

4664 Arboretum Cir 101, NAPLES

2 Beds 2 Baths 1,406 SqFt Rental MLS® # 226001767

Realty One Group MVP

New New

$5,500

2730 Cypress Trace Cir 2820, NAPLES

2 Beds 2 Baths 1,373 SqFt Rental MLS® # 226027557

SunStream Realty

New New

$5,500

5 Bluebill Ave 303-1, NAPLES

2 Beds 2 Baths 1,068 SqFt Rental MLS® # 226030982

Berkshire Hathaway FL Realty

New New

$5,500

5455 Worthington Ln 103, NAPLES

2 Beds 2 Baths 1,202 SqFt Rental MLS® # 226030943

Premier Sotheby's Int'l Realty

$5,500

9727 Acqua Ct 444, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226030352

WeichertRealtors-ParadiseHomes

$5,500

1285 Sweetwater Cv 2106, NAPLES

2 Beds 2 Baths 1,378 SqFt Rental MLS® # 226029868

Coldwell Banker Realty

$5,500

9735 Acqua Ct 611, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226029676

Naples Breeze Realty

$5,500

↓ $1,000

9596 Trevi Ct 5435, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226028991

Parkline Realty

$5,500

8357 Rimini Way, NAPLES

3 Beds 3 Baths 1,890 SqFt Rental MLS® # 226028400

Veronawalk Realty, Inc.

$5,500

↓ $250

4402 Novato Ct, NAPLES

3 Beds 2 Baths 1,983 SqFt Rental MLS® # 226026582

John R Wood Properties

$5,500

4147 Los Altos Ct, NAPLES

2 Beds 2 Baths 1,540 SqFt Rental MLS® # 226026856

Coastal Intl Properties LLC

$5,500

9566 Trevi Ct 4944, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226025813

Bluewater Signature Realty LLC

$5,500

8693 Querce Ct, NAPLES

2 Beds 2 Baths 1,415 SqFt Rental MLS® # 226024740

Veronawalk Realty, Inc.

$5,500

1415 Sweetwater Cv 104, NAPLES

3 Beds 2 Baths 1,381 SqFt Rental MLS® # 226024443

Coldwell Banker Realty

$5,500

1222 Gordon Dr 2, NAPLES

2 Beds 2 Baths 1,125 SqFt Rental MLS® # 226022848

Compass Florida LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,900

141 Bristol Ln C-21, NAPLES

$5,800

1417 Chesapeake Ave 104, NAPLES

$5,800

7345 Rockefeller Dr, NAPLES

$5,800

6900 Dennis Cir J-205, NAPLES

$5,800

9022 Michael Cir 4, NAPLES

$5,800

9419 Benvenuto Ct 204, NAPLES

$5,795

3985 Deer Crossing Ct 201, NAPLES

$5,750

2604 Sailors Way 120, NAPLES

$5,750

2190 Arielle Dr 902, NAPLES

$5,750

500 Misty Pines Cir 206, NAPLES

$5,750

7828 Gardner Dr 5-202, NAPLES

$5,700

9088 Chula Vista St 108-3, NAPLES

$5,650

5125 Cedar Springs Dr 204, NAPLES

$5,600

3048 Horizon Ln 1103, NAPLES

$5,600

640 Luisa Ln 804-4, NAPLES

$5,550

4664 Arboretum Cir 101, NAPLES

$5,500

2730 Cypress Trace Cir 2820, NAPLES

$5,500

5 Bluebill Ave 303-1, NAPLES

$5,500

5455 Worthington Ln 103, NAPLES

$5,500

9727 Acqua Ct 444, NAPLES

$5,500

1285 Sweetwater Cv 2106, NAPLES

$5,500

9735 Acqua Ct 611, NAPLES

$5,500

9596 Trevi Ct 5435, NAPLES

$5,500

8357 Rimini Way, NAPLES

$5,500

4402 Novato Ct, NAPLES

$5,500

4147 Los Altos Ct, NAPLES

$5,500

9566 Trevi Ct 4944, NAPLES

$5,500

8693 Querce Ct, NAPLES

$5,500

1415 Sweetwater Cv 104, NAPLES

$5,500

1222 Gordon Dr 2, NAPLES