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

$28,000

16476 Talis Park Dr, NAPLES

3 Beds 4 Baths 3,198 SqFt Rental MLS® # 226007766

John R Wood Properties

$27,500

9200 Mercato Way, NAPLES

3 Beds 4 Baths 2,708 SqFt Rental MLS® # 226022631

Premier Sotheby's Int'l Realty

$27,000

6597 Nicholas Blvd 306, NAPLES

3 Beds 3 Baths 3,225 SqFt Rental MLS® # 226022983

William Raveis Real Estate

$26,500

590 E Lake Dr, NAPLES

4 Beds 3 Baths 2,500 SqFt Rental MLS® # 226005478

Royal Shell Real Estate, Inc.

$26,500

↓ $500

2764 Tiburon Blvd E 3-101, NAPLES

3 Beds 4 Baths 2,950 SqFt Rental MLS® # 225070441

Real Estate Specialty Svcs II

$26,000

270 5th Ave S H-2, NAPLES

4 Beds 5 Baths 3,576 SqFt Rental MLS® # 226016782

William Raveis Real Estate

$26,000

2750 Treasure Ln, NAPLES

4 Beds 4 Baths 5,412 SqFt Rental MLS® # 226008675

Douglas Elliman Florida, LLC

$26,000

↓ $2,000

2543 Marquesa Royale Ln Ph 301, NAPLES

3 Beds 4 Baths 2,950 SqFt Rental MLS® # 225069126

Real Estate Specialty Svcs II

New New

$25,000

503 Neapolitan Way, NAPLES

4 Beds 3 Baths 3,382 SqFt Rental MLS® # 226030660

John R Wood Properties

$25,000

4751 Gulf Shore Blvd N 1408, NAPLES

3 Beds 2 Baths 1,980 SqFt Rental MLS® # 226027460

Premier Sotheby's Int'l Realty

$25,000

816 Turkey Oak Ln, NAPLES

3 Beds 3 Baths 2,231 SqFt Rental MLS® # 226023150

Premier Sotheby's Int'l Realty

$25,000

4041 Gulf Shore Blvd N Ph-4, NAPLES

3 Beds 3 Baths 2,575 SqFt Rental MLS® # 226024477

Hamro & Associates LLC

$25,000

819 91st Ave N, NAPLES

4 Beds 4 Baths 1,926 SqFt Rental MLS® # 226023438

Naples Vibe Realty, LLC

$25,000

↑ $1,000

420 Palm Cir E, NAPLES

4 Beds 4 Baths 2,930 SqFt Rental MLS® # 226022366

Compass Florida LLC

$25,000

9431 Galliano Ter, NAPLES

3 Beds 4 Baths 2,850 SqFt Rental MLS® # 226021321

Coldwell Banker Realty

$25,000

374 14th Ave S, NAPLES

3 Beds 4 Baths 2,369 SqFt Rental MLS® # 226020306

Downing Frye Realty Inc.

$25,000

275 Indies Way 1703, NAPLES

3 Beds 3 Baths 2,747 SqFt Rental MLS® # 226019247

William Raveis Real Estate

$25,000

2538 Marquesa Royale Ln Ph 5-301, NAPLES

3 Beds 4 Baths 3,000 SqFt Rental MLS® # 226014407

Real Estate Specialty Svcs II

$25,000

265 Indies Way 1404, NAPLES

3 Beds 3 Baths 2,798 SqFt Rental MLS® # 226018317

Keller Williams Realty Naples

$25,000

1199 9th Ave N, NAPLES

3 Beds 2 Baths 2,000 SqFt Rental MLS® # 226018201

William Raveis Real Estate

$25,000

4083 Belair Ln, NAPLES

3 Beds 4 Baths 2,600 SqFt Rental MLS® # 226017269

Realty One Group MVP

$25,000

4401 Gulf Shore Blvd N Ph3, NAPLES

3 Beds 3 Baths 2,511 SqFt Rental MLS® # 226013709

John R Wood Properties

$25,000

9902 Corso Bello Dr, NAPLES

5 Beds 5 Baths 3,542 SqFt Rental MLS® # 226015989

Safe Harbor Real Estate Servic

$25,000

596 111th Ave N, NAPLES

4 Beds 5 Baths 3,350 SqFt Rental MLS® # 226009652

Sun Realty

$25,000

4041 Gulf Shore Blvd N Ph-7, NAPLES

2 Beds 3 Baths 2,240 SqFt Rental MLS® # 226008732

Hamro & Associates LLC

$25,000

4916 Crayton Rd, NAPLES

3 Beds 2 Baths 1,932 SqFt Rental MLS® # 226005027

William Raveis Real Estate

$25,000

↑ $5,000

11238 Five Oaks Ln, NAPLES

3 Beds 5 Baths 3,522 SqFt Rental MLS® # 226003240

Premier Sotheby's Int'l Realty

$25,000

↑ $10,000

2700 Lantern Ln, NAPLES

3 Beds 3 Baths 3,095 SqFt Rental MLS® # 225079875

Royal Shell Real Estate, Inc.

$25,000

2630 Bolero Dr 2-2, NAPLES

3 Beds 2 Baths 2,256 SqFt Rental MLS® # 225066893

William Raveis Real Estate

$25,000

1900 Sandpiper St, NAPLES

3 Beds 3 Baths 2,653 SqFt Rental MLS® # 225074081

Premier Sotheby's Int'l Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$28,000

16476 Talis Park Dr, NAPLES

$27,500

9200 Mercato Way, NAPLES

$27,000

6597 Nicholas Blvd 306, NAPLES

$26,500

590 E Lake Dr, NAPLES

$26,500

2764 Tiburon Blvd E 3-101, NAPLES

$26,000

270 5th Ave S H-2, NAPLES

$26,000

2750 Treasure Ln, NAPLES

$26,000

2543 Marquesa Royale Ln Ph 301, NAPLES

$25,000

503 Neapolitan Way, NAPLES

$25,000

4751 Gulf Shore Blvd N 1408, NAPLES

$25,000

816 Turkey Oak Ln, NAPLES

$25,000

4041 Gulf Shore Blvd N Ph-4, NAPLES

$25,000

819 91st Ave N, NAPLES

$25,000

420 Palm Cir E, NAPLES

$25,000

9431 Galliano Ter, NAPLES

$25,000

374 14th Ave S, NAPLES

$25,000

275 Indies Way 1703, NAPLES

$25,000

2538 Marquesa Royale Ln Ph 5-301, NAPLES

$25,000

265 Indies Way 1404, NAPLES

$25,000

1199 9th Ave N, NAPLES

$25,000

4083 Belair Ln, NAPLES

$25,000

4401 Gulf Shore Blvd N Ph3, NAPLES

$25,000

9902 Corso Bello Dr, NAPLES

$25,000

596 111th Ave N, NAPLES

$25,000

4041 Gulf Shore Blvd N Ph-7, NAPLES

$25,000

4916 Crayton Rd, NAPLES

$25,000

11238 Five Oaks Ln, NAPLES

$25,000

2700 Lantern Ln, NAPLES

$25,000

2630 Bolero Dr 2-2, NAPLES

$25,000

1900 Sandpiper St, NAPLES