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

$15,000

↑ $2,000

365 5th Ave S 303, NAPLES

2 Beds 2 Baths 1,090 SqFt Rental MLS® # 226009218

Parkline Realty

$15,000

6215 Brunello Ln, NAPLES

3 Beds 3 Baths 2,062 SqFt Rental MLS® # 226006825

Premier Sotheby's Int'l Realty

$15,000

↑ $3,000

11118 Gulf Shore Dr A401, NAPLES

2 Beds 2 Baths 1,476 SqFt Rental MLS® # 226001762

William Raveis Real Estate

$15,000

↑ $5,000

9124 Raintree St, NAPLES

3 Beds 3 Baths 2,366 SqFt Rental MLS® # 226001363

Berkshire Hathaway FL Realty

$15,000

↑ $1,000

6849 Grenadier Blvd 1602, NAPLES

2 Beds 2 Baths 1,640 SqFt Rental MLS® # 226000981

William Raveis Real Estate

$15,000

9332 Fieldstone Ln, NAPLES

3 Beds 3 Baths 2,384 SqFt Rental MLS® # 226000023

Exp Realty LLC

$15,000

9560 Firenze Cir, NAPLES

5 Beds 4 Baths 2,900 SqFt Rental MLS® # 225084830

Waterfront Realty Group Inc

$15,000

10851 Gulf Shore Dr 402, NAPLES

2 Beds 2 Baths 1,562 SqFt Rental MLS® # 225085053

William Raveis Real Estate

$15,000

15804 Derna St, NAPLES

3 Beds 3 Baths 2,337 SqFt Rental MLS® # 225082027

William Raveis Real Estate

$15,000

1125 Central Ave 469, NAPLES

2 Beds 3 Baths 1,935 SqFt Rental MLS® # 225083409

Compass Florida LLC

$15,000

7797 Ashton Rd, NAPLES

2 Beds 3 Baths 2,871 SqFt Rental MLS® # 225083219

Premier Sotheby's Int'l Realty

$15,000

400 Flagship Dr 1104, NAPLES

3 Beds 3 Baths 1,750 SqFt Rental MLS® # 225079012

Downing Frye Realty Inc.

$15,000

↑ $7,000

9260 Cormorant Dr, NAPLES

3 Beds 3 Baths 2,488 SqFt Rental MLS® # 225081584

John R Wood Properties

$15,000

9051 Gulf Shore Dr Ph3, NAPLES

3 Beds 3 Baths 2,175 SqFt Rental MLS® # 225076271

John R Wood Properties

$15,000

2662 Bolero Dr 10, NAPLES

2 Beds 2 Baths 1,768 SqFt Rental MLS® # 225074759

William Raveis Real Estate

$15,000

9569 Siracusa Ct, NAPLES

3 Beds 3 Baths 2,392 SqFt Rental MLS® # 225070773

Safe Harbor Real Estate Servic

$15,000

6573 Marissa Loop 1403, NAPLES

2 Beds 2 Baths 1,341 SqFt Rental MLS® # 225070545

Coldwell Banker Realty

$14,850

9287 Chiasso Cove Ct, NAPLES

3 Beds 4 Baths 3,280 SqFt Rental MLS® # 225081132

John R Wood Properties

$14,750

6658 Trident Way J4, NAPLES

3 Beds 3 Baths 1,900 SqFt Rental MLS® # 226025131

Compass Florida LLC

$14,500

2175 Antigua Ln, NAPLES

3 Beds 5 Baths 2,785 SqFt Rental MLS® # 226021625

Berkshire Hathaway FL Realty

$14,500

805 Bentwater Cir 104, NAPLES

3 Beds 3 Baths 1,831 SqFt Rental MLS® # 226020118

William Raveis Real Estate

$14,500

400 Flagship Dr 902, NAPLES

3 Beds 3 Baths 2,035 SqFt Rental MLS® # 226018454

William Raveis Real Estate

$14,500

↓ $500

7763 Winding Cypress Dr, NAPLES

4 Beds 3 Baths 3,077 SqFt Rental MLS® # 226001830

REMAX Affinity Mercato

$14,500

707 104th Ave N, NAPLES

3 Beds 2 Baths 1,745 SqFt Rental MLS® # 225081280

John R Wood Properties

$14,500

↑ $500

400 Flagship Dr 403, NAPLES

3 Beds 3 Baths 2,035 SqFt Rental MLS® # 225073692

William Raveis Real Estate

$14,500

↑ $4,500

1236 13th Ave N, NAPLES

3 Beds 2 Baths 1,461 SqFt Rental MLS® # 225070575

Compass Florida LLC

New New

$14,000

7040 Pelican Bay Blvd D405, NAPLES

3 Beds 2 Baths 2,111 SqFt Rental MLS® # 226030295

John R Wood Properties

$14,000

4551 Gulf Shore Blvd N 201, NAPLES

2 Beds 2 Baths 1,829 SqFt Rental MLS® # 226029098

Real Estate Specialty Svcs II

$14,000

7352 Lantana Way, NAPLES

3 Beds 3 Baths 2,651 SqFt Rental MLS® # 226029397

Coldwell Banker Realty

$14,000

400 Flagship Dr 1002, NAPLES

3 Beds 3 Baths 2,035 SqFt Rental MLS® # 226029541

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$15,000

365 5th Ave S 303, NAPLES

$15,000

6215 Brunello Ln, NAPLES

$15,000

11118 Gulf Shore Dr A401, NAPLES

$15,000

9124 Raintree St, NAPLES

$15,000

6849 Grenadier Blvd 1602, NAPLES

$15,000

9332 Fieldstone Ln, NAPLES

$15,000

9560 Firenze Cir, NAPLES

$15,000

10851 Gulf Shore Dr 402, NAPLES

$15,000

15804 Derna St, NAPLES

$15,000

1125 Central Ave 469, NAPLES

$15,000

7797 Ashton Rd, NAPLES

$15,000

400 Flagship Dr 1104, NAPLES

$15,000

9260 Cormorant Dr, NAPLES

$15,000

9051 Gulf Shore Dr Ph3, NAPLES

$15,000

2662 Bolero Dr 10, NAPLES

$15,000

9569 Siracusa Ct, NAPLES

$15,000

6573 Marissa Loop 1403, NAPLES

$14,850

9287 Chiasso Cove Ct, NAPLES

$14,750

6658 Trident Way J4, NAPLES

$14,500

2175 Antigua Ln, NAPLES

$14,500

805 Bentwater Cir 104, NAPLES

$14,500

400 Flagship Dr 902, NAPLES

$14,500

7763 Winding Cypress Dr, NAPLES

$14,500

707 104th Ave N, NAPLES

$14,500

400 Flagship Dr 403, NAPLES

$14,500

1236 13th Ave N, NAPLES

$14,000

7040 Pelican Bay Blvd D405, NAPLES

$14,000

4551 Gulf Shore Blvd N 201, NAPLES

$14,000

7352 Lantana Way, NAPLES

$14,000

400 Flagship Dr 1002, NAPLES