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

$8,000

2261 Kings Lake Blvd, NAPLES

3 Beds 2 Baths 1,600 SqFt Rental MLS® # 226026497

Royal Shell Real Estate, Inc.

$8,000

7124 Saona Ct, NAPLES

2 Beds 2 Baths 1,387 SqFt Rental MLS® # 226025164

John R Wood Properties

$8,000

8437 Abbington Cir 612, NAPLES

2 Beds 2 Baths 1,825 SqFt Rental MLS® # 226025407

Royal Shell Real Estate, Inc.

$8,000

8845 Lely Island Cir, NAPLES

3 Beds 2 Baths 2,373 SqFt Rental MLS® # 226023369

Downing Frye Realty Inc.

$8,000

4300 Belair Ln 12, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226018167

William Raveis Real Estate

$8,000

271 Southbay Dr 235, NAPLES

2 Beds 2 Baths 1,075 SqFt Rental MLS® # 226020050

SunStream Realty

$8,000

6155 Dogleg Dr, NAPLES

3 Beds 2 Baths 2,043 SqFt Rental MLS® # 226021348

Downing Frye Realty Inc.

$8,000

3 Bluebill Ave 303, NAPLES

2 Beds 2 Baths 1,071 SqFt Rental MLS® # 226018057

Downing Frye Realty Inc.

$8,000

1977 Gulf Shore Blvd N 306, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226019648

Royal Shell Real Estate, Inc.

$8,000

4200 Belair Ln 114, NAPLES

3 Beds 2 Baths 1,542 SqFt Rental MLS® # 226019323

Royal Shell Real Estate, Inc.

$8,000

6017 Trophy Dr 601, NAPLES

3 Beds 2 Baths 2,160 SqFt Rental MLS® # 226019000

Premier Property Management

$8,000

1296 Grand Canal Dr, NAPLES

3 Beds 2 Baths 1,614 SqFt Rental MLS® # 226018220

Compass Florida LLC

$8,000

9834 Giaveno 1732, NAPLES

2 Beds 2 Baths 1,137 SqFt Rental MLS® # 226017160

Safe Harbor Real Estate Servic

$8,000

9715 Acqua Ct 136, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226017155

Safe Harbor Real Estate Servic

$8,000

↑ $4,250

1910 Gulf Shore Blvd N 107, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226017087

William Raveis Real Estate

$8,000

14541 Stern Way, NAPLES

2 Beds 2 Baths 1,819 SqFt Rental MLS® # 226011627

John R Wood Properties

$8,000

563 Serendipity Dr 563, NAPLES

2 Beds 2 Baths 1,545 SqFt Rental MLS® # 226016090

Royal Shell Real Estate, Inc.

$8,000

9834 Giaveno Cir 1746, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226015986

Safe Harbor Real Estate Servic

$8,000

3279 Tahoe Ct, NAPLES

3 Beds 3 Baths 2,213 SqFt Rental MLS® # 226015432

Florida Home Realty, Inc.

$8,000

7104 Barrington Cir 3-102, NAPLES

3 Beds 2 Baths 1,527 SqFt Rental MLS® # 226015306

Premier Property Management

$8,000

↓ $1,000

1119 Ridge St, NAPLES

3 Beds 4 Baths 2,221 SqFt Rental MLS® # 226010597

William Raveis Real Estate

$8,000

379 Grace Bay Ln, NAPLES

3 Beds 2 Baths 1,816 SqFt Rental MLS® # 226012084

Coastal Intl Properties LLC

$8,000

16390 Viansa Way 1-202, NAPLES

3 Beds 4 Baths 2,350 SqFt Rental MLS® # 226011204

RMC REALTY INTERNATIONAL

$8,000

↓ $4,000

11030 Gulf Shore Dr 202, NAPLES

3 Beds 2 Baths 1,770 SqFt Rental MLS® # 226008188

Downing Frye Realty Inc.

$8,000

1190 Egrets Walk Cir 103, NAPLES

3 Beds 2 Baths 1,507 SqFt Rental MLS® # 226008060

Naples Trust Real Estate Servi

$8,000

6753 Bent Grass Dr, NAPLES

3 Beds 3 Baths 1,945 SqFt Rental MLS® # 226006785

Coastal Intl Properties LLC

$8,000

8138 Saratoga Dr 2201, NAPLES

2 Beds 2 Baths 1,880 SqFt Rental MLS® # 226005938

Downing Frye Realty Inc.

$8,000

↑ $3,000

2215 Chesterbrook Ct 203, NAPLES

2 Beds 2 Baths 1,433 SqFt Rental MLS® # 226001650

Sun Realty

$8,000

↑ $3,000

905 13th St N, NAPLES

3 Beds 2 Baths 1,292 SqFt Rental MLS® # 226001290

Florida Home Realty, Inc.

$8,000

1 Bluebill Ave 412, NAPLES

2 Beds 2 Baths 1,050 SqFt Rental MLS® # 226000229

Serhant-Naples

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$8,000

2261 Kings Lake Blvd, NAPLES

$8,000

7124 Saona Ct, NAPLES

$8,000

8437 Abbington Cir 612, NAPLES

$8,000

8845 Lely Island Cir, NAPLES

$8,000

4300 Belair Ln 12, NAPLES

$8,000

271 Southbay Dr 235, NAPLES

$8,000

6155 Dogleg Dr, NAPLES

$8,000

3 Bluebill Ave 303, NAPLES

$8,000

1977 Gulf Shore Blvd N 306, NAPLES

$8,000

4200 Belair Ln 114, NAPLES

$8,000

6017 Trophy Dr 601, NAPLES

$8,000

1296 Grand Canal Dr, NAPLES

$8,000

9834 Giaveno 1732, NAPLES

$8,000

9715 Acqua Ct 136, NAPLES

$8,000

1910 Gulf Shore Blvd N 107, NAPLES

$8,000

14541 Stern Way, NAPLES

$8,000

563 Serendipity Dr 563, NAPLES

$8,000

9834 Giaveno Cir 1746, NAPLES

$8,000

3279 Tahoe Ct, NAPLES

$8,000

7104 Barrington Cir 3-102, NAPLES

$8,000

1119 Ridge St, NAPLES

$8,000

379 Grace Bay Ln, NAPLES

$8,000

16390 Viansa Way 1-202, NAPLES

$8,000

11030 Gulf Shore Dr 202, NAPLES

$8,000

1190 Egrets Walk Cir 103, NAPLES

$8,000

6753 Bent Grass Dr, NAPLES

$8,000

8138 Saratoga Dr 2201, NAPLES

$8,000

2215 Chesterbrook Ct 203, NAPLES

$8,000

905 13th St N, NAPLES

$8,000

1 Bluebill Ave 412, NAPLES