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

$4,200

↓ $800

5 Bluebill Ave 104, NAPLES

1 Bed 1 Bath 817 SqFt Rental MLS® # 226016159

Realty One Group MVP

$4,200

2684 Kings Lake Blvd 203, NAPLES

2 Beds 2 Baths 962 SqFt Rental MLS® # 226025276

REMAX Affinity Mercato

$4,200

9071 Albion Ln N 5703, NAPLES

2 Beds 3 Baths 1,520 SqFt Rental MLS® # 226022794

Achieve Realty LLC

$4,150

↓ $2,650

9259 Museo Cir 102, NAPLES

3 Beds 3 Baths 2,100 SqFt Rental MLS® # 226002437

John R Wood Properties

$4,100

78 Bennington Dr 5-8, NAPLES

2 Beds 2 Baths 1,562 SqFt Rental MLS® # 225078067

Compass Florida LLC

$4,100

14907 Sterling Oaks Dr, NAPLES

3 Beds 3 Baths 1,760 SqFt Rental MLS® # 226023645

Premiere Plus Realty Company

$4,000

1080 Hampton Cir, NAPLES

3 Beds 3 Baths 1,580 SqFt Rental MLS® # 226021698

WeichertRealtors-ParadiseHomes

$4,000

180 Furse Lakes Cir E8, NAPLES

2 Beds 2 Baths 1,425 SqFt Rental MLS® # 226016637

William Raveis Real Estate

$4,000

↓ $2,500

14567 Edgewater Cir, NAPLES

2 Beds 2 Baths 1,515 SqFt Rental MLS® # 226024373

Coldwell Banker Realty

$4,000

6670 Huntington Lakes Cir 103, NAPLES

2 Beds 2 Baths 1,107 SqFt Rental MLS® # 226020045

SunStream Realty

$4,000

↑ $1,500

1001 Eastham Way 106, NAPLES

2 Beds 2 Baths 1,091 SqFt Rental MLS® # 226022358

Premiere Plus Realty Company

$4,000

2738 Tiburon Blvd E B-104, NAPLES

2 Beds 2 Baths 1,420 SqFt Rental MLS® # 225079086

Coldwell Banker Realty

$4,000

12955 Positano Cir 104, NAPLES

2 Beds 2 Baths 1,067 SqFt Rental MLS® # 226010747

Grice Realty Inc

$4,000

↑ $1,200

602 111th Ave N, NAPLES

2 Beds 2 Baths 1,104 SqFt Rental MLS® # 225081768

Downing Frye Realty Inc.

$4,000

↓ $8,000

3399 Gulf Shore Blvd N 309, NAPLES

2 Beds 2 Baths 1,581 SqFt Rental MLS® # 226028174

Parkline Realty

$4,000

5778 Greenwood Cir, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 226014042

Royal Shell Real Estate, Inc.

$4,000

4610 Saint Croix Ln 1027, NAPLES

3 Beds 2 Baths 1,196 SqFt Rental MLS® # 226001780

William Raveis Real Estate

$4,000

705 Augusta Blvd 705-4, NAPLES

2 Beds 2 Baths 1,125 SqFt Rental MLS® # 226010512

Waterfront Realty Group Inc

$4,000

470 Launch Cir 403, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226018423

William Raveis Real Estate

$4,000

2748 Tiburon Blvd E C-301, NAPLES

1 Bed 2 Baths 1,160 SqFt Rental MLS® # 225054810

Real Estate Specialty Svcs II

$4,000

↑ $500

240 Pebble Beach Blvd 702, NAPLES

2 Beds 2 Baths 1,090 SqFt Rental MLS® # 225073424

Coldwell Banker Realty

$4,000

4180 Looking Glass Ln 4104, NAPLES

2 Beds 2 Baths 1,246 SqFt Rental MLS® # 226014072

Royal Shell Real Estate, Inc.

$4,000

↑ $200

714 11th St N, NAPLES

3 Beds 2 Baths 1,183 SqFt Rental MLS® # 225080215

Royal Shell Real Estate, Inc.

$4,000

751 100th Ave N, NAPLES

2 Beds 1 Bath 912 SqFt Rental MLS® # 225082268

Realty Hub

$4,000

9731 Acqua Ct 531, NAPLES

2 Beds 2 Baths 1,284 SqFt Rental MLS® # 226010064

WeichertRealtors-ParadiseHomes

$4,000

↓ $500

725 Saratoga Cir A101, NAPLES

3 Beds 2 Baths 1,320 SqFt Rental MLS® # 226000366

Realty One Group MVP

$4,000

709 Augusta Blvd 709-5, NAPLES

3 Beds 2 Baths 1,480 SqFt Rental MLS® # 226024294

Waterfront Realty Group Inc

$4,000

134 Cypress Way E 305, NAPLES

2 Beds 2 Baths 1,064 SqFt Rental MLS® # 226014377

Marzucco Real Estate

$4,000

↓ $3,000

9596 Trevi Ct 5428, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226015885

Realty One Group MVP

$4,000

6875 Saona Ct, NAPLES

2 Beds 2 Baths 1,565 SqFt Rental MLS® # 226028175

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$4,200

5 Bluebill Ave 104, NAPLES

$4,200

2684 Kings Lake Blvd 203, NAPLES

$4,200

9071 Albion Ln N 5703, NAPLES

$4,150

9259 Museo Cir 102, NAPLES

$4,100

78 Bennington Dr 5-8, NAPLES

$4,100

14907 Sterling Oaks Dr, NAPLES

$4,000

1080 Hampton Cir, NAPLES

$4,000

180 Furse Lakes Cir E8, NAPLES

$4,000

14567 Edgewater Cir, NAPLES

$4,000

6670 Huntington Lakes Cir 103, NAPLES

$4,000

1001 Eastham Way 106, NAPLES

$4,000

2738 Tiburon Blvd E B-104, NAPLES

$4,000

12955 Positano Cir 104, NAPLES

$4,000

602 111th Ave N, NAPLES

$4,000

3399 Gulf Shore Blvd N 309, NAPLES

$4,000

5778 Greenwood Cir, NAPLES

$4,000

4610 Saint Croix Ln 1027, NAPLES

$4,000

705 Augusta Blvd 705-4, NAPLES

$4,000

470 Launch Cir 403, NAPLES

$4,000

2748 Tiburon Blvd E C-301, NAPLES

$4,000

240 Pebble Beach Blvd 702, NAPLES

$4,000

4180 Looking Glass Ln 4104, NAPLES

$4,000

714 11th St N, NAPLES

$4,000

751 100th Ave N, NAPLES

$4,000

9731 Acqua Ct 531, NAPLES

$4,000

725 Saratoga Cir A101, NAPLES

$4,000

709 Augusta Blvd 709-5, NAPLES

$4,000

134 Cypress Way E 305, NAPLES

$4,000

9596 Trevi Ct 5428, NAPLES

$4,000

6875 Saona Ct, NAPLES