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

$6,000

2170 Gulf Shore Blvd N 41e, NAPLES

1 Bed 1 Bath 682 SqFt Rental MLS® # 226029347

Luxe Naples Real Estate

New New

$6,000

1325 Oceania Dr N 6, NAPLES

2 Beds 1 Bath 1,200 SqFt Rental MLS® # 226030839

Royal Shell Real Estate, Inc.

$6,000

6910 Satinleaf Rd N 101, NAPLES

3 Beds 2 Baths 1,616 SqFt Rental MLS® # 226030630

WeichertRealtors-ParadiseHomes

$6,000

6361 Pelican Bay Blvd 402, NAPLES

2 Beds 2 Baths 1,456 SqFt Rental MLS® # 226030589

William Raveis Real Estate

$6,000

451 Bayfront Pl 5311, NAPLES

3 Beds 2 Baths 1,869 SqFt Rental MLS® # 226020692

Premiere Plus Realty Company

$6,000

6585 Nicholas Blvd 1702, NAPLES

2 Beds 2 Baths 1,341 SqFt Rental MLS® # 226030076

John R Wood Properties

$6,000

2450 Old Groves Rd 201, NAPLES

2 Beds 2 Baths 1,569 SqFt Rental MLS® # 226030074

William Raveis Real Estate

$6,000

2281 16th St Ne, NAPLES

3 Beds 2 Baths 1,558 SqFt Rental MLS® # 226029995

Mato Realty, LLC

$6,000

9560 Trevi Ct 4812, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226029454

WeichertRealtors-ParadiseHomes

$6,000

8986 Cambria Cir 2203, NAPLES

2 Beds 2 Baths 1,404 SqFt Rental MLS® # 226027627

John R Wood Properties

$6,000

5941 Sand Wedge Ln 1206, NAPLES

2 Beds 2 Baths 1,478 SqFt Rental MLS® # 226028304

Premier Sotheby's Int'l Realty

$6,000

1325 Oceania Dr N 6, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226028558

Royal Shell Real Estate, Inc.

$6,000

8965 Malibu Ln 802, NAPLES

3 Beds 2 Baths 1,771 SqFt Rental MLS® # 226028117

Xclusive Homes LLC

$6,000

9102 Capistrano St S 7209, NAPLES

2 Beds 3 Baths 1,494 SqFt Rental MLS® # 226023985

DomainRealty.com LLC

$6,000

7360 Glenmoor Ln 4301, NAPLES

2 Beds 2 Baths 954 SqFt Rental MLS® # 226027213

William Raveis Real Estate

$6,000

555 Park Shore Dr B408, NAPLES

2 Beds 2 Baths 1,045 SqFt Rental MLS® # 226023783

Premier Sotheby's Int'l Realty

$6,000

1599 Marton Ct, NAPLES

2 Beds 2 Baths 1,900 SqFt Rental MLS® # 226024786

Waterfront Realty Group Inc

$6,000

1980 Willow Bend Cir 7-204, NAPLES

2 Beds 2 Baths 1,592 SqFt Rental MLS® # 226023491

Naples Vacation Properties

$6,000

↓ $500

9433 Benvenuto Ct 201, NAPLES

2 Beds 2 Baths 1,528 SqFt Rental MLS® # 226022806

Naples Trust Real Estate Servi

$6,000

2983 Binnacle Dr, NAPLES

3 Beds 2 Baths 1,866 SqFt Rental MLS® # 226022749

Naples Vacation Properties

$6,000

1634 Tarpon Bay Dr S 202, NAPLES

3 Beds 2 Baths 2,170 SqFt Rental MLS® # 226020048

SunStream Realty

$6,000

↓ $250

3296 Twilight Ln 6202, NAPLES

3 Beds 3 Baths 2,133 SqFt Rental MLS® # 226021359

DomainRealty.com LLC

$6,000

6548 Monterey Pt 204, NAPLES

3 Beds 3 Baths 2,288 SqFt Rental MLS® # 226020871

Coldwell Banker Realty

$6,000

2004 Tarpon Bay Dr N 201, NAPLES

3 Beds 2 Baths 2,170 SqFt Rental MLS® # 226018989

SunStream Realty

$6,000

↓ $500

822 Gulf Pavillion Dr 202, NAPLES

2 Beds 2 Baths 1,275 SqFt Rental MLS® # 226019653

Premier Sotheby's Int'l Realty

$6,000

522 Beachwalk Cir, NAPLES

2 Beds 2 Baths 1,359 SqFt Rental MLS® # 226018838

WeichertRealtors-ParadiseHomes

$6,000

↓ $500

9115 Strada Pl 5501, NAPLES

2 Beds 2 Baths 1,550 SqFt Rental MLS® # 226018669

Premier Sotheby's Int'l Realty

$6,000

↓ $500

9683 Lipari Ct, NAPLES

4 Beds 5 Baths 3,250 SqFt Rental MLS® # 226018607

WeichertRealtors-ParadiseHomes

$6,000

9115 Capistrano St S 8207, NAPLES

2 Beds 3 Baths 1,494 SqFt Rental MLS® # 226011640

William Raveis Real Estate

$6,000

↓ $300

766 Central Ave 312, NAPLES

2 Beds 2 Baths 855 SqFt Rental MLS® # 226017843

Naples Flat Fee Realty LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$6,000

2170 Gulf Shore Blvd N 41e, NAPLES

$6,000

1325 Oceania Dr N 6, NAPLES

$6,000

6910 Satinleaf Rd N 101, NAPLES

$6,000

6361 Pelican Bay Blvd 402, NAPLES

$6,000

451 Bayfront Pl 5311, NAPLES

$6,000

6585 Nicholas Blvd 1702, NAPLES

$6,000

2450 Old Groves Rd 201, NAPLES

$6,000

2281 16th St Ne, NAPLES

$6,000

9560 Trevi Ct 4812, NAPLES

$6,000

8986 Cambria Cir 2203, NAPLES

$6,000

5941 Sand Wedge Ln 1206, NAPLES

$6,000

1325 Oceania Dr N 6, NAPLES

$6,000

8965 Malibu Ln 802, NAPLES

$6,000

9102 Capistrano St S 7209, NAPLES

$6,000

7360 Glenmoor Ln 4301, NAPLES

$6,000

555 Park Shore Dr B408, NAPLES

$6,000

1599 Marton Ct, NAPLES

$6,000

1980 Willow Bend Cir 7-204, NAPLES

$6,000

9433 Benvenuto Ct 201, NAPLES

$6,000

2983 Binnacle Dr, NAPLES

$6,000

1634 Tarpon Bay Dr S 202, NAPLES

$6,000

3296 Twilight Ln 6202, NAPLES

$6,000

6548 Monterey Pt 204, NAPLES

$6,000

2004 Tarpon Bay Dr N 201, NAPLES

$6,000

822 Gulf Pavillion Dr 202, NAPLES

$6,000

522 Beachwalk Cir, NAPLES

$6,000

9115 Strada Pl 5501, NAPLES

$6,000

9683 Lipari Ct, NAPLES

$6,000

9115 Capistrano St S 8207, NAPLES

$6,000

766 Central Ave 312, NAPLES