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

$4,500

856 98th Ave N, NAPLES

3 Beds 2 Baths 1,711 SqFt Rental MLS® # 226009468

Naples Trust Real Estate Servi

$4,500

45 Wickliffe Dr, NAPLES

4 Beds 2 Baths 1,749 SqFt Rental MLS® # 226004184

Coldwell Banker Realty

$4,500

1100 8th Ave S 209c, NAPLES

2 Beds 2 Baths 1,008 SqFt Rental MLS® # 226011632

William Raveis Real Estate

$4,500

↓ $500

3002 Sandpiper Bay Cir A306, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226022351

Naples Flat Fee Realty LLC

$4,500

56 Silver Oaks Cir 102, NAPLES

2 Beds 2 Baths 1,373 SqFt Rental MLS® # 226014799

Coldwell Banker Realty

$4,500

↓ $1,000

6000 Pelican Bay Blvd 1202, NAPLES

2 Beds 2 Baths 1,430 SqFt Rental MLS® # 226022649

Premiere Plus Realty Company

$4,500

6934 Rain Lily Ct 102, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 225079000

William Raveis Real Estate

$4,500

1 Bluebill Ave 405, NAPLES

0 Beds 1 Bath 524 SqFt Rental MLS® # 226024094

SunStream Realty

$4,500

1100 Eastham Way A-105, NAPLES

2 Beds 2 Baths 1,184 SqFt Rental MLS® # 225083053

WeichertRealtors-ParadiseHomes

New New

$4,500

7812 Emerald Cir 201, NAPLES

3 Beds 2 Baths 1,200 SqFt Rental MLS® # 226031298

Royal Shell Real Estate, Inc.

$4,500

↓ $500

7790 Woodbrook Cir 2603, NAPLES

3 Beds 3 Baths 1,406 SqFt Rental MLS® # 225077110

KW Elevate Luxury

$4,500

2728 Tiburon Blvd E 105, NAPLES

2 Beds 3 Baths 1,865 SqFt Rental MLS® # 226021662

William Raveis Real Estate

$4,500

14321 Manchester Dr, NAPLES

3 Beds 2 Baths 2,248 SqFt Rental MLS® # 226015341

Waterfront Realty Group Inc

$4,500

↓ $500

6680 Beach Resort Dr 1210, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 225082633

Waterfront Realty Group Inc

$4,500

6680 Beach Resort Dr 1214, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 225082725

Waterfront Realty Group Inc

$4,500

2925 Cypress Trace Cir 201, NAPLES

2 Beds 2 Baths 1,094 SqFt Rental MLS® # 226019318

Keller Williams Realty Naples

$4,500

11118 Gulf Shore Dr A203, NAPLES

2 Beds 2 Baths 1,470 SqFt Rental MLS® # 226010805

Real Estate Specialty Svcs II

$4,500

N/A, NAPLES

1 Bed 2 Baths 881 SqFt Rental MLS® # 226012560

Premier Sotheby's Int'l Realty

$4,500

96 Glades Blvd 513, NAPLES

2 Beds 2 Baths 1,270 SqFt Rental MLS® # 226026292

WeichertRealtors-ParadiseHomes

$4,500

7194 Dominica Dr, NAPLES

2 Beds 2 Baths 1,565 SqFt Rental MLS® # 225073113

Compass Florida LLC

$4,500

77 Silver Oaks Cir 8102, NAPLES

2 Beds 2 Baths 1,373 SqFt Rental MLS® # 226027969

Realty One Group MVP

$4,500

106 Siena Way 1508, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226009228

Downing Frye Realty Inc.

$4,500

8125 Celeste Dr 5216, NAPLES

3 Beds 2 Baths 1,640 SqFt Rental MLS® # 226025812

Bluewater Signature Realty LLC

$4,500

6215 Wilshire Pines Cir 1601, NAPLES

3 Beds 2 Baths 1,592 SqFt Rental MLS® # 226010372

Downing Frye Realty Inc.

$4,500

230 W Naomi Dr 4702, NAPLES

2 Beds 2 Baths 1,756 SqFt Rental MLS® # 225078475

Downing Frye Realty Inc.

$4,500

2790 Cypress Trace Cir 2225, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226020542

Premier Property Management

$4,500

↓ $3,500

9508 Ironstone Ter 2-201, NAPLES

3 Beds 3 Baths 2,297 SqFt Rental MLS® # 226017433

Opyt Realty Inc

$4,500

↓ $1,000

341 Emerald Bay Cir T5, NAPLES

3 Beds 2 Baths 1,611 SqFt Rental MLS® # 225069781

Florida Home Realty, Inc.

$4,500

1262 Barrigona Ct, NAPLES

4 Beds 3 Baths 2,347 SqFt Rental MLS® # 226023045

Alfred Robbins Realty Group

$4,500

360 Horse Creek Dr 107, NAPLES

2 Beds 2 Baths 1,326 SqFt Rental MLS® # 226024421

Star Rental & Property Mngt

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$4,500

856 98th Ave N, NAPLES

$4,500

45 Wickliffe Dr, NAPLES

$4,500

1100 8th Ave S 209c, NAPLES

$4,500

3002 Sandpiper Bay Cir A306, NAPLES

$4,500

56 Silver Oaks Cir 102, NAPLES

$4,500

6000 Pelican Bay Blvd 1202, NAPLES

$4,500

6934 Rain Lily Ct 102, NAPLES

$4,500

1 Bluebill Ave 405, NAPLES

$4,500

1100 Eastham Way A-105, NAPLES

$4,500

7812 Emerald Cir 201, NAPLES

$4,500

7790 Woodbrook Cir 2603, NAPLES

$4,500

2728 Tiburon Blvd E 105, NAPLES

$4,500

14321 Manchester Dr, NAPLES

$4,500

6680 Beach Resort Dr 1210, NAPLES

$4,500

6680 Beach Resort Dr 1214, NAPLES

$4,500

2925 Cypress Trace Cir 201, NAPLES

$4,500

11118 Gulf Shore Dr A203, NAPLES

$4,500

N/A, NAPLES

$4,500

96 Glades Blvd 513, NAPLES

$4,500

7194 Dominica Dr, NAPLES

$4,500

77 Silver Oaks Cir 8102, NAPLES

$4,500

106 Siena Way 1508, NAPLES

$4,500

8125 Celeste Dr 5216, NAPLES

$4,500

6215 Wilshire Pines Cir 1601, NAPLES

$4,500

230 W Naomi Dr 4702, NAPLES

$4,500

2790 Cypress Trace Cir 2225, NAPLES

$4,500

9508 Ironstone Ter 2-201, NAPLES

$4,500

341 Emerald Bay Cir T5, NAPLES

$4,500

1262 Barrigona Ct, NAPLES

$4,500

360 Horse Creek Dr 107, NAPLES