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

$7,000

14265 Manchester Dr, NAPLES

4 Beds 2 Baths 2,362 SqFt Rental MLS® # 226024157

Berkshire Hathaway FL Realty

$7,000

801 River Point Dr 206a, NAPLES

2 Beds 2 Baths 803 SqFt Rental MLS® # 226023872

Gulf Coast International Lux R

$7,000

559 Beachwalk Cir U-203, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226023734

Realty One Group MVP

$7,000

5601 Turtle Bay Dr 302, NAPLES

2 Beds 2 Baths 2,009 SqFt Rental MLS® # 226023392

Realty One Group MVP

$7,000

8355 Whisper Trace Way K104, NAPLES

3 Beds 2 Baths 1,674 SqFt Rental MLS® # 226023436

Naples Vibe Realty, LLC

$7,000

3250 W Crown Pointe Blvd 101, NAPLES

3 Beds 2 Baths 1,653 SqFt Rental MLS® # 226022576

Berkshire Hathaway FL Realty

$7,000

817 Regency Reserve Cir 3901, NAPLES

2 Beds 2 Baths 2,058 SqFt Rental MLS® # 226021623

Berkshire Hathaway FL Realty

$7,000

8989 Cambria Cir 1807, NAPLES

3 Beds 3 Baths 2,008 SqFt Rental MLS® # 226016209

Downing Frye Realty Inc.

$7,000

1812 Avian Ct A78, NAPLES

2 Beds 2 Baths 1,579 SqFt Rental MLS® # 226018178

Waterfront Realty Group Inc

$7,000

9513 Avellino Way 2024, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 226018649

WeichertRealtors-ParadiseHomes

$7,000

410 Bayfront Pl 2204, NAPLES

2 Beds 2 Baths 1,223 SqFt Rental MLS® # 226017992

Berkshire Hathaway FL Realty

$7,000

9584 Trevi Ct 5223, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226017887

Safe Harbor Real Estate Servic

$7,000

1051 3rd St S 301, NAPLES

2 Beds 2 Baths 1,256 SqFt Rental MLS® # 226017342

Downing Frye Realty Inc.

$7,000

410 Flagship Dr 301 (terrace), NAPLES

3 Beds 3 Baths 1,979 SqFt Rental MLS® # 226017200

William Raveis Real Estate

$7,000

5705 Heron Ln 806, NAPLES

2 Beds 2 Baths 1,540 SqFt Rental MLS® # 226016590

Royal Shell Real Estate, Inc.

$7,000

8125 Celeste Dr 5113, NAPLES

3 Beds 2 Baths 1,635 SqFt Rental MLS® # 226014652

Berkshire Hathaway FL Realty

$7,000

5060 Coldstream Ln, NAPLES

3 Beds 2 Baths 2,035 SqFt Rental MLS® # 226013968

Waterfront Realty Group Inc

$7,000

↑ $4,500

91 Georgetown Blvd 91, NAPLES

2 Beds 2 Baths 1,450 SqFt Rental MLS® # 226013318

DC Fiene Realty

$7,000

9572 Trevi Ct 5015, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226012819

WeichertRealtors-ParadiseHomes

$7,000

9521 Avellino Way 2426, NAPLES

2 Beds 2 Baths 1,569 SqFt Rental MLS® # 226011043

WeichertRealtors-ParadiseHomes

$7,000

9517 Avellino Way 2214, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 226010013

WeichertRealtors-ParadiseHomes

$7,000

9820 Giaveno Cir 1413, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226009358

WeichertRealtors-ParadiseHomes

$7,000

↓ $1,000

N/A, NAPLES

1 Bed 1 Bath 817 SqFt Rental MLS® # 226005189

Coldwell Banker Realty

$7,000

10317 Heritage Bay Blvd 1416, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226006777

Downing Frye Realty Inc.

$7,000

↓ $500

13628 Mandarin Cir, NAPLES

2 Beds 2 Baths 1,978 SqFt Rental MLS® # 226003230

John R Wood Properties

$7,000

980 7th Ave S 109, NAPLES

1 Bed 1 Bath 540 SqFt Rental MLS® # 226001386

Re/Max Alliance Group

$7,000

401 Bayfront Pl 3405, NAPLES

2 Beds 2 Baths 1,223 SqFt Rental MLS® # 226001917

Naples Trust Real Estate Servi

$7,000

↓ $500

4200 Belair Ln 316, NAPLES

2 Beds 2 Baths 1,213 SqFt Rental MLS® # 226001042

William Raveis Real Estate

$7,000

9832 Venezia Cir 1013, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 225084499

Safe Harbor Real Estate Servic

$7,000

↓ $1,000

834 Gulf Pavilion Dr 204, NAPLES

2 Beds 2 Baths 1,516 SqFt Rental MLS® # 225081835

DomainRealty.com LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$7,000

14265 Manchester Dr, NAPLES

$7,000

801 River Point Dr 206a, NAPLES

$7,000

559 Beachwalk Cir U-203, NAPLES

$7,000

5601 Turtle Bay Dr 302, NAPLES

$7,000

8355 Whisper Trace Way K104, NAPLES

$7,000

3250 W Crown Pointe Blvd 101, NAPLES

$7,000

817 Regency Reserve Cir 3901, NAPLES

$7,000

8989 Cambria Cir 1807, NAPLES

$7,000

1812 Avian Ct A78, NAPLES

$7,000

9513 Avellino Way 2024, NAPLES

$7,000

410 Bayfront Pl 2204, NAPLES

$7,000

9584 Trevi Ct 5223, NAPLES

$7,000

1051 3rd St S 301, NAPLES

$7,000

410 Flagship Dr 301 (terrace), NAPLES

$7,000

5705 Heron Ln 806, NAPLES

$7,000

8125 Celeste Dr 5113, NAPLES

$7,000

5060 Coldstream Ln, NAPLES

$7,000

91 Georgetown Blvd 91, NAPLES

$7,000

9572 Trevi Ct 5015, NAPLES

$7,000

9521 Avellino Way 2426, NAPLES

$7,000

9517 Avellino Way 2214, NAPLES

$7,000

9820 Giaveno Cir 1413, NAPLES

$7,000

N/A, NAPLES

$7,000

10317 Heritage Bay Blvd 1416, NAPLES

$7,000

13628 Mandarin Cir, NAPLES

$7,000

980 7th Ave S 109, NAPLES

$7,000

401 Bayfront Pl 3405, NAPLES

$7,000

4200 Belair Ln 316, NAPLES

$7,000

9832 Venezia Cir 1013, NAPLES

$7,000

834 Gulf Pavilion Dr 204, NAPLES