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

$5,500

↑ $1,300

5045 Cedar Springs Dr 203, NAPLES

2 Beds 2 Baths 1,427 SqFt Rental MLS® # 225082984

Parkline Realty

$5,500

1300 Gulf Shore Blvd N 407, NAPLES

2 Beds 2 Baths 850 SqFt Rental MLS® # 225082409

William Raveis Real Estate

$5,500

69 Georgetown Blvd 69, NAPLES

2 Beds 2 Baths 1,450 SqFt Rental MLS® # 225079755

DC Fiene Realty

$5,500

↓ $500

671 100th Ave N, NAPLES

3 Beds 2 Baths 1,164 SqFt Rental MLS® # 224055793

Easy Living Property Services

$5,500

↑ $600

333 Harbour Dr 211, NAPLES

2 Beds 2 Baths 975 SqFt Rental MLS® # 225074540

Naples Flat Fee Realty LLC

$5,500

300 Horse Creek Dr 408, NAPLES

2 Beds 2 Baths 1,434 SqFt Rental MLS® # 225074053

Premier Sotheby's Int'l Realty

$5,500

840 Gulf Pavillion Dr 103, NAPLES

2 Beds 2 Baths 1,179 SqFt Rental MLS® # 225073993

Premier Sotheby's Int'l Realty

$5,500

450 Bayfront Pl 4201, NAPLES

1 Bed 1 Bath 852 SqFt Rental MLS® # 225070437

Compass Florida LLC

$5,500

1025 Tarpon Cove Dr 203, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225072135

Premier Sotheby's Int'l Realty

$5,500

↑ $100

4523 Fluvia Ave, NAPLES

2 Beds 1 Bath 1,050 SqFt Rental MLS® # 225070487

John R Wood Properties

$5,500

2730 Cypress Trace Cir 2820, NAPLES

2 Beds 2 Baths 1,373 SqFt Rental MLS® # 225067176

SunStream Realty

New New

$5,400

6934 Rain Lily Ct 103, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 226027533

SunStream Realty

$5,400

↑ $200

2001 Tarpon Bay Dr N 102, NAPLES

2 Beds 2 Baths 1,620 SqFt Rental MLS® # 2025023161

Fort Myers Beach Realty

$5,400

↓ $600

13105 Vanderbilt Dr 802, NAPLES

2 Beds 2 Baths 1,390 SqFt Rental MLS® # 225073771

Florida Home Realty, Inc.

$5,300

513 Lake Louise Cir 202, NAPLES

2 Beds 2 Baths 1,444 SqFt Rental MLS® # 226029049

Downing Frye Realty Inc.

$5,300

↑ $2,800

270 Naples Cove Dr 3506, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226021296

WeichertRealtors-ParadiseHomes

$5,300

788 Park Shore Dr H36, NAPLES

1 Bed 2 Baths 848 SqFt Rental MLS® # 226017632

Coldwell Banker Realty

$5,300

788 Park Shore Dr D30, NAPLES

2 Beds 2 Baths 1,015 SqFt Rental MLS® # 226013602

John R Wood Properties

$5,300

2720 Cypress Trace Cir 2920, NAPLES

3 Beds 2 Baths 1,373 SqFt Rental MLS® # 226008273

Exp Realty LLC

$5,250

3500 Gulf Shore Blvd N 408, NAPLES

2 Beds 2 Baths 1,196 SqFt Rental MLS® # 226025767

John R Wood Properties

$5,250

807 River Point Dr 102d, NAPLES

1 Bed 2 Baths 1,100 SqFt Rental MLS® # 226027345

William Raveis Real Estate

$5,250

2541 Citrus Lake Dr A-205, NAPLES

3 Beds 2 Baths 1,590 SqFt Rental MLS® # 226006138

Downing Frye Realty Inc.

$5,250

2671 Citrus Lake Dr E-201, NAPLES

3 Beds 2 Baths 1,380 SqFt Rental MLS® # 226006134

Downing Frye Realty Inc.

$5,250

2885 Citrus Lake Dr N103, NAPLES

2 Beds 2 Baths 1,249 SqFt Rental MLS® # 226000078

Downing Frye Realty Inc.

$5,200

3060 Horizon Ln 1404, NAPLES

3 Beds 3 Baths 1,818 SqFt Rental MLS® # 226025685

Naples Flat Fee Realty LLC

$5,200

↓ $300

2815 Cypress Trace Cir 2-101, NAPLES

2 Beds 2 Baths 1,252 SqFt Rental MLS® # 226002897

West Shore Properties RE,MNGT

$5,200

306 Palm Dr 2, NAPLES

2 Beds 2 Baths 1,270 SqFt Rental MLS® # 226023364

Napoli Realty Services, LLC

$5,200

1912 Tarpon Bay Dr N, NAPLES

2 Beds 2 Baths 1,566 SqFt Rental MLS® # 226021128

SunStream Realty

$5,200

↑ $200

6816 Satinleaf Rd S 102, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 226015248

SunStream Realty

$5,200

9267 Museo Ct 204, NAPLES

3 Beds 4 Baths 2,100 SqFt Rental MLS® # 226015901

Premier Property Management

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,500

5045 Cedar Springs Dr 203, NAPLES

$5,500

1300 Gulf Shore Blvd N 407, NAPLES

$5,500

69 Georgetown Blvd 69, NAPLES

$5,500

671 100th Ave N, NAPLES

$5,500

333 Harbour Dr 211, NAPLES

$5,500

300 Horse Creek Dr 408, NAPLES

$5,500

840 Gulf Pavillion Dr 103, NAPLES

$5,500

450 Bayfront Pl 4201, NAPLES

$5,500

1025 Tarpon Cove Dr 203, NAPLES

$5,500

4523 Fluvia Ave, NAPLES

$5,500

2730 Cypress Trace Cir 2820, NAPLES

$5,400

6934 Rain Lily Ct 103, NAPLES

$5,400

2001 Tarpon Bay Dr N 102, NAPLES

$5,400

13105 Vanderbilt Dr 802, NAPLES

$5,300

513 Lake Louise Cir 202, NAPLES

$5,300

270 Naples Cove Dr 3506, NAPLES

$5,300

788 Park Shore Dr H36, NAPLES

$5,300

788 Park Shore Dr D30, NAPLES

$5,300

2720 Cypress Trace Cir 2920, NAPLES

$5,250

3500 Gulf Shore Blvd N 408, NAPLES

$5,250

807 River Point Dr 102d, NAPLES

$5,250

2541 Citrus Lake Dr A-205, NAPLES

$5,250

2671 Citrus Lake Dr E-201, NAPLES

$5,250

2885 Citrus Lake Dr N103, NAPLES

$5,200

3060 Horizon Ln 1404, NAPLES

$5,200

2815 Cypress Trace Cir 2-101, NAPLES

$5,200

306 Palm Dr 2, NAPLES

$5,200

1912 Tarpon Bay Dr N, NAPLES

$5,200

6816 Satinleaf Rd S 102, NAPLES

$5,200

9267 Museo Ct 204, NAPLES