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

$7,500

9584 Trevi Ct 5214, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226027861

WeichertRealtors-ParadiseHomes

$7,500

2215 Arielle Dr 1203, NAPLES

3 Beds 2 Baths 1,845 SqFt Rental MLS® # 226027590

Premier Sotheby's Int'l Realty

$7,500

N/A, NAPLES

3 Beds 3 Baths 2,373 SqFt Rental MLS® # 226026997

Fast Action Realty Inc

$7,500

3000 Gulf Shore Blvd N 213, NAPLES

2 Beds 2 Baths 1,113 SqFt Rental MLS® # 226027098

Coldwell Banker Realty

$7,500

250 7th Ave S 305, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226026745

Waterfront Realty Group Inc

$7,500

9584 Trevi Ct 5226, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226026807

WeichertRealtors-ParadiseHomes

$7,500

9572 Trevi Ct 5045, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226026702

Real Estate Specialty Svcs II

$7,500

1265 Egrets Lndg 201, NAPLES

2 Beds 2 Baths 1,800 SqFt Rental MLS® # 226026738

Royal Shell Real Estate, Inc.

$7,500

697 Crossfield Cir, NAPLES

3 Beds 2 Baths 1,764 SqFt Rental MLS® # 226025377

William Raveis Real Estate

$7,500

9079 Cascada Way 102, NAPLES

3 Beds 2 Baths 2,408 SqFt Rental MLS® # 226024626

Achieve Realty LLC

$7,500

565 Beachwalk Cir T104, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 226023074

Realty One Group MVP

$7,500

9441 Benvenuto Ct 102, NAPLES

2 Beds 2 Baths 1,528 SqFt Rental MLS® # 226022914

Naples Vibe Realty, LLC

$7,500

855 Reef Point Cir, NAPLES

2 Beds 2 Baths 1,359 SqFt Rental MLS® # 226021753

Realty One Group MVP

$7,500

↓ $2,500

3328 Runaway Ln, NAPLES

4 Beds 3 Baths 2,818 SqFt Rental MLS® # 226017217

Compass Florida LLC

$7,500

613 Beachwalk Cir J, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226021660

Realty One Group MVP

$7,500

3951 Ruxton Rd, NAPLES

3 Beds 2 Baths 2,385 SqFt Rental MLS® # 226019531

Downing Frye Realty Inc.

$7,500

7204 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,308 SqFt Rental MLS® # 226018718

Premier Sotheby's Int'l Realty

$7,500

163 Indies Dr E 106, NAPLES

3 Beds 2 Baths 1,698 SqFt Rental MLS® # 226019739

Realty One Group MVP

$7,500

2134 Palm St, NAPLES

1 Bed 1 Bath 600 SqFt Rental MLS® # 226016730

John R Wood Properties

$7,500

9525 Ironstone Ter 102, NAPLES

3 Beds 2 Baths 1,654 SqFt Rental MLS® # 226018534

Opyt Realty Inc

$7,500

9514 Avellino Way 2113, NAPLES

2 Beds 2 Baths 1,366 SqFt Rental MLS® # 226017166

Safe Harbor Real Estate Servic

$7,500

9073 Rialto St 6002, NAPLES

3 Beds 2 Baths 1,771 SqFt Rental MLS® # 226017169

Berkshire Hathaway FL Realty

$7,500

9830 Giaveno Cir 1615, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226016643

Safe Harbor Real Estate Servic

Open House

$7,500

2728 Tiburon Blvd E Ph-503, NAPLES

3 Beds 4 Baths 2,985 SqFt Rental

Open House

Fri, Sep 18th, 2026 @ 2pm - 4pm

MLS® # 226015794

Real Estate Specialty Svcs II

$7,500

631 Beachwalk Cir F204, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 226015789

William Raveis Real Estate

$7,500

9509 Avellino Way 1815, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 226014915

Safe Harbor Real Estate Servic

$7,500

9596 Trevi Ct 5426, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226014840

Naples Vacation Properties

$7,500

9727 Acqua Ct 425, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226014831

WeichertRealtors-ParadiseHomes

$7,500

15181 Butler Lake Dr 201, NAPLES

3 Beds 2 Baths 2,152 SqFt Rental MLS® # 226014370

DomainRealty.com LLC

$7,500

9731 Acqua Ct 523, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226012804

WeichertRealtors-ParadiseHomes

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$7,500

9584 Trevi Ct 5214, NAPLES

$7,500

2215 Arielle Dr 1203, NAPLES

$7,500

N/A, NAPLES

$7,500

3000 Gulf Shore Blvd N 213, NAPLES

$7,500

250 7th Ave S 305, NAPLES

$7,500

9584 Trevi Ct 5226, NAPLES

$7,500

9572 Trevi Ct 5045, NAPLES

$7,500

1265 Egrets Lndg 201, NAPLES

$7,500

697 Crossfield Cir, NAPLES

$7,500

9079 Cascada Way 102, NAPLES

$7,500

565 Beachwalk Cir T104, NAPLES

$7,500

9441 Benvenuto Ct 102, NAPLES

$7,500

855 Reef Point Cir, NAPLES

$7,500

3328 Runaway Ln, NAPLES

$7,500

613 Beachwalk Cir J, NAPLES

$7,500

3951 Ruxton Rd, NAPLES

$7,500

7204 Cayo Coco Ln, NAPLES

$7,500

163 Indies Dr E 106, NAPLES

$7,500

2134 Palm St, NAPLES

$7,500

9525 Ironstone Ter 102, NAPLES

$7,500

9514 Avellino Way 2113, NAPLES

$7,500

9073 Rialto St 6002, NAPLES

$7,500

9830 Giaveno Cir 1615, NAPLES

$7,500

2728 Tiburon Blvd E Ph-503, NAPLES

$7,500

631 Beachwalk Cir F204, NAPLES

$7,500

9509 Avellino Way 1815, NAPLES

$7,500

9596 Trevi Ct 5426, NAPLES

$7,500

9727 Acqua Ct 425, NAPLES

$7,500

15181 Butler Lake Dr 201, NAPLES

$7,500

9731 Acqua Ct 523, NAPLES