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

$14,000

5550 Heron Point Dr 504, NAPLES

3 Beds 2 Baths 1,514 SqFt Rental MLS® # 225069818

Royal Shell Real Estate, Inc.

$13,750

300 Dunes Blvd 602, NAPLES

3 Beds 3 Baths 2,194 SqFt Rental MLS® # 226019251

William Raveis Real Estate

New New

$13,500

4551 Gulf Shore Blvd N 605, NAPLES

2 Beds 2 Baths 1,800 SqFt Rental MLS® # 226028478

Real Estate Specialty Svcs II

New New

$13,500

2847 Tiburon Blvd E 8-101, NAPLES

2 Beds 2 Baths 2,159 SqFt Rental MLS® # 226030669

Naples Trust Real Estate Servi

$13,500

10701 Gulf Shore Dr 401, NAPLES

2 Beds 3 Baths 1,961 SqFt Rental MLS® # 226027350

SunStream Realty

$13,500

4551 Gulf Shore Blvd N 1001, NAPLES

2 Beds 2 Baths 1,829 SqFt Rental MLS® # 226023245

Real Estate Specialty Svcs II

$13,500

3500 Gulf Shore Blvd N 408, NAPLES

2 Beds 2 Baths 1,196 SqFt Rental MLS® # 226025338

John R Wood Properties

$13,500

2864 Tiburon Blvd E 101, NAPLES

2 Beds 2 Baths 2,159 SqFt Rental MLS® # 226018193

William Raveis Real Estate

$13,500

3126 Terramar Ct, NAPLES

3 Beds 3 Baths 2,990 SqFt Rental MLS® # 226021580

Epique Realty, INC

$13,500

400 Flagship Dr 604, NAPLES

3 Beds 3 Baths 1,760 SqFt Rental MLS® # 226018451

William Raveis Real Estate

$13,500

5501 Heron Point Dr 501, NAPLES

2 Beds 2 Baths 1,450 SqFt Rental MLS® # 226008945

William Raveis Real Estate

$13,500

10475 Gulf Shore Dr 113, NAPLES

2 Beds 2 Baths 1,315 SqFt Rental MLS® # 225084739

SunStream Realty

$13,500

↑ $3,500

1222 Gordon Dr 14, NAPLES

2 Beds 3 Baths 1,200 SqFt Rental MLS® # 225073581

John R Wood Properties

$13,500

6652 Trident Way J-1, NAPLES

2 Beds 3 Baths 1,955 SqFt Rental MLS® # 225072125

Premier Sotheby's Int'l Realty

$13,500

↑ $1,000

4255 Gulf Shore Blvd N 407, NAPLES

2 Beds 2 Baths 1,714 SqFt Rental MLS® # 225070817

Premier Sotheby's Int'l Realty

$13,250

↓ $250

5550 Heron Point Dr 503, NAPLES

2 Beds 2 Baths 1,263 SqFt Rental MLS® # 226019615

Excel Real Estate Services Inc

$13,200

460 Launch Cir 202, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226024255

William Raveis Real Estate

$13,000

7778 Ashton Rd, NAPLES

3 Beds 2 Baths 1,975 SqFt Rental MLS® # 226030635

Premier Sotheby's Int'l Realty

$13,000

7040 Pelican Bay Blvd 504, NAPLES

2 Beds 2 Baths 1,550 SqFt Rental MLS® # 226030033

John R Wood Properties

$13,000

4001 Gulf Shore Blvd N 302, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226018762

RE/MAX Hallmark Realty

$13,000

4001 Gulf Shore Blvd N 500, NAPLES

2 Beds 3 Baths 1,646 SqFt Rental MLS® # 226025865

RE/MAX Hallmark Realty

$13,000

222 Harbour Dr 105, NAPLES

2 Beds 2 Baths 1,393 SqFt Rental MLS® # 226025923

Royal Shell Real Estate, Inc.

$13,000

14614 Stillwater Way, NAPLES

4 Beds 4 Baths 2,431 SqFt Rental MLS® # 226024887

Berkshire Hathaway FL Realty

$13,000

N/A, NAPLES

2 Beds 3 Baths 1,505 SqFt Rental MLS® # 226021978

Luxe Naples Real Estate

$13,000

325 Dunes Blvd 306, NAPLES

2 Beds 3 Baths 2,194 SqFt Rental MLS® # 226020055

SunStream Realty

$13,000

315 Dunes Blvd 404, NAPLES

3 Beds 2 Baths 1,950 SqFt Rental MLS® # 226018405

William Raveis Real Estate

$13,000

9115 Strada Pl 5501, NAPLES

2 Beds 2 Baths 1,550 SqFt Rental MLS® # 226018667

Premier Sotheby's Int'l Realty

$13,000

7687 Pebble Creek Cir 301, NAPLES

3 Beds 3 Baths 1,800 SqFt Rental MLS® # 226015772

Royal Shell Real Estate, Inc.

$13,000

7687 Pebble Creek Cir 403, NAPLES

3 Beds 2 Baths 1,641 SqFt Rental MLS® # 226010389

Edina Realty, Inc

$13,000

↑ $7,150

N/A, NAPLES

3 Beds 3 Baths 2,704 SqFt Rental MLS® # 225079569

Coldwell Banker Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$14,000

5550 Heron Point Dr 504, NAPLES

$13,750

300 Dunes Blvd 602, NAPLES

$13,500

4551 Gulf Shore Blvd N 605, NAPLES

$13,500

2847 Tiburon Blvd E 8-101, NAPLES

$13,500

10701 Gulf Shore Dr 401, NAPLES

$13,500

4551 Gulf Shore Blvd N 1001, NAPLES

$13,500

3500 Gulf Shore Blvd N 408, NAPLES

$13,500

2864 Tiburon Blvd E 101, NAPLES

$13,500

3126 Terramar Ct, NAPLES

$13,500

400 Flagship Dr 604, NAPLES

$13,500

5501 Heron Point Dr 501, NAPLES

$13,500

10475 Gulf Shore Dr 113, NAPLES

$13,500

1222 Gordon Dr 14, NAPLES

$13,500

6652 Trident Way J-1, NAPLES

$13,500

4255 Gulf Shore Blvd N 407, NAPLES

$13,250

5550 Heron Point Dr 503, NAPLES

$13,200

460 Launch Cir 202, NAPLES

$13,000

7778 Ashton Rd, NAPLES

$13,000

7040 Pelican Bay Blvd 504, NAPLES

$13,000

4001 Gulf Shore Blvd N 302, NAPLES

$13,000

4001 Gulf Shore Blvd N 500, NAPLES

$13,000

222 Harbour Dr 105, NAPLES

$13,000

14614 Stillwater Way, NAPLES

$13,000

N/A, NAPLES

$13,000

325 Dunes Blvd 306, NAPLES

$13,000

315 Dunes Blvd 404, NAPLES

$13,000

9115 Strada Pl 5501, NAPLES

$13,000

7687 Pebble Creek Cir 301, NAPLES

$13,000

7687 Pebble Creek Cir 403, NAPLES

$13,000

N/A, NAPLES