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

$5,000

202 Peppermint Ln 2, NAPLES

2 Beds 2 Baths 1,335 SqFt Rental MLS® # 225082871

Napoli Realty Services, LLC

$5,000

↑ $500

3051 Sandpiper Bay Cir I102, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 225082299

Naples Flat Fee Realty LLC

$5,000

3380 Crown Pointe Blvd W 102, NAPLES

3 Beds 2 Baths 1,516 SqFt Rental MLS® # 225068949

Coldwell Banker Realty

$5,000

2895 Cypress Trace Cir 202, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226028804

Achieve Realty LLC

$5,000

124 Penny Ln 778, NAPLES

2 Beds 2 Baths 1,532 SqFt Rental MLS® # 226028059

Bluewater Signature Realty LLC

$5,000

9566 Trevi Ct 4943, NAPLES

2 Beds 2 Baths 1,107 SqFt Rental MLS® # 226018045

Premier Property Management

New New

$4,995

9159 Delano St 9905, NAPLES

3 Beds 2 Baths 1,770 SqFt Rental MLS® # 226030823

Premier Property Management

$4,995

↓ $255

14265 Manchester Dr, NAPLES

4 Beds 2 Baths 2,362 SqFt Rental MLS® # 226011601

Berkshire Hathaway FL Realty

$4,995

4126 Belair Ln B-10, NAPLES

2 Beds 2 Baths 1,195 SqFt Rental MLS® # 226018575

Current Property Management

$4,950

↓ $200

3048 Horizon Ln 1104, NAPLES

3 Beds 3 Baths 1,818 SqFt Rental MLS® # 226016799

Premier Property Management

$4,950

↑ $2,450

541 Windsor Sq, NAPLES

2 Beds 2 Baths 1,421 SqFt Rental MLS® # 226005085

Alpizar & Company, LLC

$4,900

↑ $2,700

153 Bristol Ln F102, NAPLES

2 Beds 2 Baths 1,009 SqFt Rental MLS® # 226011122

Alpizar & Company, LLC

$4,900

337 Emerald Bay Cir U1, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 225073990

Downing Frye Realty Inc.

$4,900

↑ $1,150

1904 Sierra Ct, NAPLES

2 Beds 2 Baths 1,405 SqFt Rental MLS® # 225071067

Bluewater Signature Realty LLC

$4,800

440 Wiggins Lake Ct 201, NAPLES

2 Beds 2 Baths 1,283 SqFt Rental MLS® # 226011187

Grice Realty Inc

$4,800

↓ $200

10842 Vanderbilt Dr, NAPLES

4 Beds 3 Baths 2,402 SqFt Rental MLS® # 226017368

Naples Trust Real Estate Servi

$4,800

555 Park Shore Dr B-407, NAPLES

1 Bed 2 Baths 1,045 SqFt Rental MLS® # 225073016

SunStream Realty

New New

$4,800

834 Gulf Pavilion Dr 204, NAPLES

2 Beds 2 Baths 1,516 SqFt Rental MLS® # 226030744

DomainRealty.com LLC

$4,800

↓ $700

7450 Emilia Ln, NAPLES

2 Beds 2 Baths 1,554 SqFt Rental MLS® # 226007504

Waterfront Realty Group Inc

$4,800

440 Fox Haven Dr 2106, NAPLES

2 Beds 2 Baths 1,068 SqFt Rental MLS® # 226013987

Naples Flat Fee Realty LLC

$4,800

↓ $400

2855 Cypress Trace Circle 202, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226012714

West Shore Properties RE,MNGT

$4,800

1075 Foxfire Ln 103, NAPLES

2 Beds 2 Baths 1,135 SqFt Rental MLS® # 226027157

Premier Sotheby's Int'l Realty

$4,800

1345 Sweetwater Cv 203, NAPLES

2 Beds 2 Baths 1,279 SqFt Rental MLS® # 2025017837

KHI Real Estate FM, LLC

$4,800

7380 Saint Ives Way 1204, NAPLES

2 Beds 2 Baths 1,053 SqFt Rental MLS® # 226005932

Naples Flat Fee Realty LLC

$4,750

↓ $1,100

1309 Westlake Blvd, NAPLES

4 Beds 2 Baths 1,966 SqFt Rental MLS® # 226023107

Berkshire Hathaway FL Realty

$4,750

2710 Cypress Trace Cir 3031, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 225077167

REMAX Affinity Mercato

$4,700

7477 Lourdes Ct, NAPLES

3 Beds 2 Baths 2,211 SqFt Rental MLS® # 226017839

Compass Florida LLC

$4,600

6650 Beach Resort Dr 908, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 226006214

William Raveis Real Estate

$4,600

↓ $100

120 Pebble Shores Dr 106, NAPLES

2 Beds 2 Baths 1,132 SqFt Rental MLS® # 226010399

REMAX Affinity Mercato

$4,500

↓ $250

8013 Calle Canovas Ct, NAPLES

2 Beds 2 Baths 1,552 SqFt Rental MLS® # 225077934

Berkshire Hathaway FL Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,000

202 Peppermint Ln 2, NAPLES

$5,000

3051 Sandpiper Bay Cir I102, NAPLES

$5,000

3380 Crown Pointe Blvd W 102, NAPLES

$5,000

2895 Cypress Trace Cir 202, NAPLES

$5,000

124 Penny Ln 778, NAPLES

$5,000

9566 Trevi Ct 4943, NAPLES

$4,995

9159 Delano St 9905, NAPLES

$4,995

14265 Manchester Dr, NAPLES

$4,995

4126 Belair Ln B-10, NAPLES

$4,950

3048 Horizon Ln 1104, NAPLES

$4,950

541 Windsor Sq, NAPLES

$4,900

153 Bristol Ln F102, NAPLES

$4,900

337 Emerald Bay Cir U1, NAPLES

$4,900

1904 Sierra Ct, NAPLES

$4,800

440 Wiggins Lake Ct 201, NAPLES

$4,800

10842 Vanderbilt Dr, NAPLES

$4,800

555 Park Shore Dr B-407, NAPLES

$4,800

834 Gulf Pavilion Dr 204, NAPLES

$4,800

7450 Emilia Ln, NAPLES

$4,800

440 Fox Haven Dr 2106, NAPLES

$4,800

2855 Cypress Trace Circle 202, NAPLES

$4,800

1075 Foxfire Ln 103, NAPLES

$4,800

1345 Sweetwater Cv 203, NAPLES

$4,800

7380 Saint Ives Way 1204, NAPLES

$4,750

1309 Westlake Blvd, NAPLES

$4,750

2710 Cypress Trace Cir 3031, NAPLES

$4,700

7477 Lourdes Ct, NAPLES

$4,600

6650 Beach Resort Dr 908, NAPLES

$4,600

120 Pebble Shores Dr 106, NAPLES

$4,500

8013 Calle Canovas Ct, NAPLES