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

9528 Avellino Way 2515, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226013376

WeichertRealtors-ParadiseHomes

$7,500

9731 Acqua Ct 536, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226012815

WeichertRealtors-ParadiseHomes

$7,500

6545 Valen Way F205, NAPLES

2 Beds 2 Baths 1,377 SqFt Rental MLS® # 225077842

DomainRealty.com LLC

$7,500

9572 Trevi Ct 5037, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226011037

WeichertRealtors-ParadiseHomes

$7,500

1 Bluebill Ave 604, NAPLES

2 Beds 2 Baths 1,051 SqFt Rental MLS® # 226010077

Parkline Realty

$7,500

2295 Carrington Ct 1-104, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 226009653

Sun Realty

$7,500

127 Palmetto Dunes Cir, NAPLES

3 Beds 2 Baths 1,906 SqFt Rental MLS® # 226009389

John R Wood Properties

$7,500

↑ $500

2288 Ashton Oaks Ln 7-103, NAPLES

2 Beds 2 Baths 1,700 SqFt Rental MLS® # 226007614

Downing Frye Realty Inc.

$7,500

↑ $550

6770 Pelican Bay Blvd 231, NAPLES

2 Beds 2 Baths 1,572 SqFt Rental MLS® # 226007343

Star Rental & Property Mngt

$7,500

172 Indies Dr E 101, NAPLES

3 Beds 2 Baths 1,980 SqFt Rental MLS® # 226006669

Premier Sotheby's Int'l Realty

$7,500

↓ $2,000

1000 L Ambiance Cir 201, NAPLES

3 Beds 2 Baths 1,928 SqFt Rental MLS® # 226005397

Downing Frye Realty Inc.

$7,500

↑ $1,500

8135 Celeste Dr 4218, NAPLES

2 Beds 2 Baths 1,476 SqFt Rental MLS® # 226003426

Premier Sotheby's Int'l Realty

$7,500

↑ $750

6984 Saona Ct, NAPLES

2 Beds 2 Baths 1,472 SqFt Rental MLS® # 225084659

Berkshire Hathaway FL Realty

$7,500

5630 Sherborn Dr 202, NAPLES

3 Beds 2 Baths 2,005 SqFt Rental MLS® # 225077479

William Raveis Real Estate

$7,500

710 Soll St, NAPLES

3 Beds 3 Baths 1,947 SqFt Rental MLS® # 225080534

John R Wood Properties

$7,500

↑ $1,000

4200 Belair Ln 313, NAPLES

2 Beds 2 Baths 1,600 SqFt Rental MLS® # 225080859

Royal Shell Real Estate, Inc.

$7,500

↑ $1,500

3511 17th Ave Sw, NAPLES

3 Beds 2 Baths 2,600 SqFt Rental MLS® # 225078647

REMAX Affinity Mercato

$7,500

2109 Morning Sun Ln, NAPLES

2 Beds 3 Baths 2,249 SqFt Rental MLS® # 225077795

SunStream Realty

$7,500

649 Beachwalk Cir C101, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 225077881

Realty One Group MVP

$7,500

592 Beachwalk Cir N202, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 225077958

Realty One Group MVP

$7,500

↓ $500

9393 Pocida Ct 102, NAPLES

2 Beds 2 Baths 1,528 SqFt Rental MLS® # 225076496

Berkshire Hathaway FL Realty

$7,500

↑ $1,000

1350 Misty Pines Cir E-204, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 225077116

All In Property Management LLC

$7,500

9402 Pocida Ct 204, NAPLES

2 Beds 2 Baths 1,632 SqFt Rental MLS® # 225075759

Diversified Real Estate Group

$7,500

8649 Champions Pt 1201, NAPLES

2 Beds 2 Baths 2,160 SqFt Rental MLS® # 225075542

Keller Williams Elite Realty

$7,500

271 Broad Ave S 202, NAPLES

2 Beds 2 Baths 1,500 SqFt Rental MLS® # 225074679

Coldwell Banker Realty

$7,500

271 Broad Ave S 203, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225074670

Coldwell Banker Realty

$7,500

↑ $1,500

9161 Chula Vista St 135-2, NAPLES

4 Beds 3 Baths 1,776 SqFt Rental MLS® # 225074083

Premier Sotheby's Int'l Realty

$7,500

9533 Avellino Way 2921, NAPLES

2 Beds 2 Baths 1,661 SqFt Rental MLS® # 225071830

John R Wood Properties

$7,500

↑ $1,600

2290 Carrington Ct 202, NAPLES

2 Beds 2 Baths 1,183 SqFt Rental MLS® # 225070815

Coldwell Banker Realty

$7,500

559 Beachwalk Cir U204, NAPLES

3 Beds 2 Baths 1,472 SqFt Rental MLS® # 225068847

Realty One Group MVP

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$7,500

9528 Avellino Way 2515, NAPLES

$7,500

9731 Acqua Ct 536, NAPLES

$7,500

6545 Valen Way F205, NAPLES

$7,500

9572 Trevi Ct 5037, NAPLES

$7,500

1 Bluebill Ave 604, NAPLES

$7,500

2295 Carrington Ct 1-104, NAPLES

$7,500

127 Palmetto Dunes Cir, NAPLES

$7,500

2288 Ashton Oaks Ln 7-103, NAPLES

$7,500

6770 Pelican Bay Blvd 231, NAPLES

$7,500

172 Indies Dr E 101, NAPLES

$7,500

1000 L Ambiance Cir 201, NAPLES

$7,500

8135 Celeste Dr 4218, NAPLES

$7,500

6984 Saona Ct, NAPLES

$7,500

5630 Sherborn Dr 202, NAPLES

$7,500

710 Soll St, NAPLES

$7,500

4200 Belair Ln 313, NAPLES

$7,500

3511 17th Ave Sw, NAPLES

$7,500

2109 Morning Sun Ln, NAPLES

$7,500

649 Beachwalk Cir C101, NAPLES

$7,500

592 Beachwalk Cir N202, NAPLES

$7,500

9393 Pocida Ct 102, NAPLES

$7,500

1350 Misty Pines Cir E-204, NAPLES

$7,500

9402 Pocida Ct 204, NAPLES

$7,500

8649 Champions Pt 1201, NAPLES

$7,500

271 Broad Ave S 202, NAPLES

$7,500

271 Broad Ave S 203, NAPLES

$7,500

9161 Chula Vista St 135-2, NAPLES

$7,500

9533 Avellino Way 2921, NAPLES

$7,500

2290 Carrington Ct 202, NAPLES

$7,500

559 Beachwalk Cir U204, NAPLES