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

$6,500

9165 Celeste Dr 3-303, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226005233

John R Wood Properties

$6,500

↓ $1,000

9179 Cayman Dr, NAPLES

2 Beds 2 Baths 1,569 SqFt Rental MLS® # 225083410

Safe Harbor Real Estate Servic

$6,500

↑ $1,000

794 95th Ave N, NAPLES

3 Beds 2 Baths 1,805 SqFt Rental MLS® # 226003775

Coastal Intl Properties LLC

$6,500

3320 Pilot Cir, NAPLES

4 Beds 4 Baths 3,096 SqFt Rental MLS® # 225082534

Realty One Group MVP

$6,500

8949 Malibu St 304, NAPLES

3 Beds 2 Baths 1,771 SqFt Rental MLS® # 226003508

WeichertRealtors-ParadiseHomes

$6,500

↓ $500

15 Bluebill Ave 206, NAPLES

2 Beds 2 Baths 1,493 SqFt Rental MLS® # 226002833

Downing Frye Realty Inc.

$6,500

↑ $800

1657 Serena Ave, NAPLES

5 Beds 3 Baths 2,615 SqFt Rental MLS® # 226000611

Coldwell Banker Realty

$6,500

5950 Almaden Dr, NAPLES

3 Beds 2 Baths 1,762 SqFt Rental MLS® # 226000494

Grice Realty Inc

$6,500

3445 Grand Cypress Dr 202, NAPLES

3 Beds 2 Baths 1,853 SqFt Rental MLS® # 225083424

Coldwell Banker Realty

$6,500

980 7th Ave S 204, NAPLES

1 Bed 1 Bath 540 SqFt Rental MLS® # 225082879

John R Wood Properties

$6,500

5937 Sand Wedge Ln 1507, NAPLES

2 Beds 2 Baths 1,540 SqFt Rental MLS® # 225081194

Royal Shell Real Estate, Inc.

$6,500

12839 Carrington Cir 8-102, NAPLES

3 Beds 2 Baths 2,063 SqFt Rental MLS® # 225080591

Equity Realty

$6,500

↑ $500

7259 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,411 SqFt Rental MLS® # 225077845

Bluewater Signature Realty LLC

$6,500

9560 Trevi Ct 4815, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 225077024

Safe Harbor Real Estate Servic

$6,500

↑ $500

301 Ridge Dr, NAPLES

2 Beds 2 Baths 900 SqFt Rental MLS® # 225076544

Premier Sotheby's Int'l Realty

$6,500

9826 Giaveno Cir 1537, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225075641

WeichertRealtors-ParadiseHomes

$6,500

↑ $3,000

9596 Trevi Ct 5434, NAPLES

2 Beds 2 Baths 1,107 SqFt Rental MLS® # 225074896

Safe Harbor Real Estate Servic

$6,500

9082 Capistrano St N 48-5, NAPLES

2 Beds 2 Baths 1,227 SqFt Rental MLS® # 225074064

Premier Sotheby's Int'l Realty

$6,500

9578 Trevi Ct 5122, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225073428

Coldwell Banker Realty

$6,500

↓ $2,000

4200 Belair Ln 105, NAPLES

3 Beds 2 Baths 1,473 SqFt Rental MLS® # 225073770

Real Estate Specialty Svcs II

$6,500

6487 Warwick Ave, NAPLES

2 Beds 3 Baths 2,225 SqFt Rental MLS® # 225073114

Compass Florida LLC

$6,500

14672 Edgewater Cir, NAPLES

2 Beds 2 Baths 1,519 SqFt Rental MLS® # 225068940

John R Wood Properties

$6,400

421 12th Ave S A1, NAPLES

2 Beds 1 Bath 760 SqFt Rental MLS® # 226021885

Waterfront Realty Group Inc

$6,400

7030 Lone Oak Blvd, NAPLES

3 Beds 2 Baths 1,700 SqFt Rental MLS® # 226018190

William Raveis Real Estate

$6,400

3057 Driftwood Way 4004, NAPLES

3 Beds 3 Baths 1,818 SqFt Rental MLS® # 226016772

John R Wood Properties

$6,400

2261 11th St N, NAPLES

4 Beds 2 Baths 1,428 SqFt Rental MLS® # 226013920

John R Wood Properties

$6,300

9554 Trevi Ct 4715, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226002485

Downing Frye Realty Inc.

$6,280

↑ $1,000

9081 Albion Ln S 6510, NAPLES

3 Beds 3 Baths 2,004 SqFt Rental MLS® # 225079226

eXp Realty LLC

$6,200

6914 Satinleaf Rd N 103, NAPLES

2 Beds 2 Baths 1,404 SqFt Rental MLS® # 226023343

John R Wood Properties

$6,100

2961 Sanborn Ave, NAPLES

2 Beds 4 Baths 2,000 SqFt Rental MLS® # 225076103

Waterfront Realty Group Inc

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$6,500

9165 Celeste Dr 3-303, NAPLES

$6,500

9179 Cayman Dr, NAPLES

$6,500

794 95th Ave N, NAPLES

$6,500

3320 Pilot Cir, NAPLES

$6,500

8949 Malibu St 304, NAPLES

$6,500

15 Bluebill Ave 206, NAPLES

$6,500

1657 Serena Ave, NAPLES

$6,500

5950 Almaden Dr, NAPLES

$6,500

3445 Grand Cypress Dr 202, NAPLES

$6,500

980 7th Ave S 204, NAPLES

$6,500

5937 Sand Wedge Ln 1507, NAPLES

$6,500

12839 Carrington Cir 8-102, NAPLES

$6,500

7259 Cayo Coco Ln, NAPLES

$6,500

9560 Trevi Ct 4815, NAPLES

$6,500

301 Ridge Dr, NAPLES

$6,500

9826 Giaveno Cir 1537, NAPLES

$6,500

9596 Trevi Ct 5434, NAPLES

$6,500

9082 Capistrano St N 48-5, NAPLES

$6,500

9578 Trevi Ct 5122, NAPLES

$6,500

4200 Belair Ln 105, NAPLES

$6,500

6487 Warwick Ave, NAPLES

$6,500

14672 Edgewater Cir, NAPLES

$6,400

421 12th Ave S A1, NAPLES

$6,400

7030 Lone Oak Blvd, NAPLES

$6,400

3057 Driftwood Way 4004, NAPLES

$6,400

2261 11th St N, NAPLES

$6,300

9554 Trevi Ct 4715, NAPLES

$6,280

9081 Albion Ln S 6510, NAPLES

$6,200

6914 Satinleaf Rd N 103, NAPLES

$6,100

2961 Sanborn Ave, NAPLES