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

$9,500

N/A, NAPLES

3 Beds 3 Baths 2,053 SqFt Rental MLS® # 226030323

Fast Action Realty Inc

$9,500

9115 Napoli Ct 101, NAPLES

3 Beds 2 Baths 1,741 SqFt Rental MLS® # 226025620

WeichertRealtors-ParadiseHomes

$9,500

5550 Heron Point Dr 1003, NAPLES

2 Beds 2 Baths 1,263 SqFt Rental MLS® # 226025389

Keller Williams Realty Naples

$9,500

8263 Potomac Ln, NAPLES

3 Beds 3 Baths 2,582 SqFt Rental MLS® # 226024709

Berkshire Hathaway FL Realty

$9,500

1280 Blue Point Ave C30, NAPLES

3 Beds 2 Baths 1,405 SqFt Rental MLS® # 226021206

Waterfront Realty Group Inc

$9,500

3400 Gulf Shore Blvd N M3, NAPLES

2 Beds 2 Baths 1,337 SqFt Rental MLS® # 226019317

Coldwell Banker Realty

$9,500

↓ $5,500

631 100th Ave N, NAPLES

4 Beds 3 Baths 2,160 SqFt Rental MLS® # 226019963

Coldwell Banker Realty

$9,500

2322 Butterfly Palm Dr, NAPLES

3 Beds 2 Baths 1,936 SqFt Rental MLS® # 226018292

Keller Williams Realty Naples

$9,500

14508 Sterling Oaks Dr, NAPLES

3 Beds 2 Baths 2,599 SqFt Rental MLS® # 226015475

SunStream Realty

$9,500

↑ $500

4001 Gulf Shore Blvd N 505, NAPLES

2 Beds 2 Baths 1,271 SqFt Rental MLS® # 226017427

Downing Frye Realty Inc.

$9,500

6453 Autumn Woods Blvd, NAPLES

3 Beds 2 Baths 1,729 SqFt Rental MLS® # 226013023

Berkshire Hathaway FL Realty

$9,500

9126 Napoli Ct 101, NAPLES

3 Beds 2 Baths 1,883 SqFt Rental MLS® # 226011656

WeichertRealtors-ParadiseHomes

$9,500

6361 Pelican Bay Blvd 201, NAPLES

3 Beds 2 Baths 3,000 SqFt Rental MLS® # 226003552

William Raveis Real Estate

$9,500

6687 Huntley Ln S, NAPLES

4 Beds 3 Baths 2,398 SqFt Rental MLS® # 226001637

Waterfront Realty Group Inc

$9,500

↑ $1,500

714 11th St N, NAPLES

3 Beds 2 Baths 1,183 SqFt Rental MLS® # 226000784

Royal Shell Real Estate, Inc.

$9,500

↓ $75,500

7058 Barrington Cir 102, NAPLES

2 Beds 2 Baths 1,527 SqFt Rental MLS® # 225084712

Royal Shell Real Estate, Inc.

$9,500

↑ $500

284 4th St S 103, NAPLES

2 Beds 2 Baths 979 SqFt Rental MLS® # 225082881

John R Wood Properties

$9,500

5831 Haiti Dr, NAPLES

2 Beds 2 Baths 1,565 SqFt Rental MLS® # 225077481

William Raveis Real Estate

$9,500

8471 Abbington Cir 1111, NAPLES

3 Beds 2 Baths 1,900 SqFt Rental MLS® # 225077480

William Raveis Real Estate

$9,500

↑ $1,500

1560 Clermont Dr D-201, NAPLES

3 Beds 2 Baths 2,000 SqFt Rental MLS® # 225081639

William Raveis Real Estate

$9,500

↓ $1,000

964 8th Ave S B-2, NAPLES

3 Beds 2 Baths 1,707 SqFt Rental MLS® # 225078596

Naples Flat Fee Realty LLC

$9,500

↑ $500

8081 Players Cove Dr 101, NAPLES

2 Beds 3 Baths 2,091 SqFt Rental MLS® # 225076207

Premier Sotheby's Int'l Realty

$9,500

2961 Sanborn Ave, NAPLES

2 Beds 4 Baths 2,000 SqFt Rental MLS® # 225076167

Waterfront Realty Group Inc

$9,500

3837 Ruby Way, NAPLES

4 Beds 3 Baths 2,293 SqFt Rental MLS® # 225074091

Premier Sotheby's Int'l Realty

$9,500

410 Bayfront Pl 2301, NAPLES

3 Beds 2 Baths 1,633 SqFt Rental MLS® # 225070462

Compass Florida LLC

$9,500

↓ $1,500

2680 Longboat Dr, NAPLES

3 Beds 2 Baths 1,528 SqFt Rental MLS® # 225070855

Realty Hub

$9,500

847 Tanbark Dr 101, NAPLES

3 Beds 2 Baths 1,340 SqFt Rental MLS® # 225069810

Royal Shell Real Estate, Inc.

$9,400

425 Cove Tower Dr 902, NAPLES

2 Beds 2 Baths 1,854 SqFt Rental MLS® # 226022578

Berkshire Hathaway FL Realty

$9,400

↓ $100

11118 Gulfshore 203, NAPLES

2 Beds 2 Baths 1,470 SqFt Rental MLS® # 225080136

Real Estate Specialty Svcs II

$9,250

572 105th Ave N, NAPLES

3 Beds 2 Baths 1,485 SqFt Rental MLS® # 2025017985

Realty Group of SW Florida Inc

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$9,500

N/A, NAPLES

$9,500

9115 Napoli Ct 101, NAPLES

$9,500

5550 Heron Point Dr 1003, NAPLES

$9,500

8263 Potomac Ln, NAPLES

$9,500

1280 Blue Point Ave C30, NAPLES

$9,500

3400 Gulf Shore Blvd N M3, NAPLES

$9,500

631 100th Ave N, NAPLES

$9,500

2322 Butterfly Palm Dr, NAPLES

$9,500

14508 Sterling Oaks Dr, NAPLES

$9,500

4001 Gulf Shore Blvd N 505, NAPLES

$9,500

6453 Autumn Woods Blvd, NAPLES

$9,500

9126 Napoli Ct 101, NAPLES

$9,500

6361 Pelican Bay Blvd 201, NAPLES

$9,500

6687 Huntley Ln S, NAPLES

$9,500

714 11th St N, NAPLES

$9,500

7058 Barrington Cir 102, NAPLES

$9,500

284 4th St S 103, NAPLES

$9,500

5831 Haiti Dr, NAPLES

$9,500

8471 Abbington Cir 1111, NAPLES

$9,500

1560 Clermont Dr D-201, NAPLES

$9,500

964 8th Ave S B-2, NAPLES

$9,500

8081 Players Cove Dr 101, NAPLES

$9,500

2961 Sanborn Ave, NAPLES

$9,500

3837 Ruby Way, NAPLES

$9,500

410 Bayfront Pl 2301, NAPLES

$9,500

2680 Longboat Dr, NAPLES

$9,500

847 Tanbark Dr 101, NAPLES

$9,400

425 Cove Tower Dr 902, NAPLES

$9,400

11118 Gulfshore 203, NAPLES

$9,250

572 105th Ave N, NAPLES