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

$20,000

4001 Gulf Shore Blvd N 707, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226010387

RE/MAX Hallmark Realty

$20,000

11002 Vanderbilt Dr, NAPLES

4 Beds 4 Baths 3,206 SqFt Rental MLS® # 226006342

Florida Home Realty, Inc.

$20,000

↑ $4,000

4041 Gulf Shore Blvd N 1204, NAPLES

2 Beds 2 Baths 2,000 SqFt Rental MLS® # 226005707

Royal Shell Real Estate, Inc.

$20,000

5065 Kensington High St, NAPLES

3 Beds 3 Baths 2,661 SqFt Rental MLS® # 226005529

Downing Frye Realty Inc.

$20,000

↓ $1,500

4901 Gulf Shore Blvd N 1604, NAPLES

2 Beds 3 Baths 2,019 SqFt Rental MLS® # 226003439

Douglas Elliman Florida,LLC

$20,000

↑ $6,000

3722 Rachel Ln, NAPLES

3 Beds 3 Baths 2,141 SqFt Rental MLS® # 225078686

John R Wood Properties

$20,000

↑ $2,000

9470 Galliano Ter, NAPLES

3 Beds 3 Baths 3,116 SqFt Rental MLS® # 225078275

Woodruff Property Management

$20,000

295 Grande Way 505, NAPLES

3 Beds 4 Baths 2,818 SqFt Rental MLS® # 225074783

William Raveis Real Estate

$20,000

8720 Bay Colony Dr 404, NAPLES

3 Beds 3 Baths 2,560 SqFt Rental MLS® # 225070325

William Raveis Real Estate

New New

$19,500

N/A, NAPLES

4 Beds 5 Baths 3,908 SqFt Rental MLS® # 226031070

Fast Action Realty Inc

$19,500

3423 Runaway Ct, NAPLES

4 Beds 5 Baths 3,904 SqFt Rental MLS® # 226029355

Coastal Intl Properties LLC

$19,500

3440 Runaway Ln, NAPLES

4 Beds 3 Baths 3,043 SqFt Rental MLS® # 226027054

John R Wood Properties

$19,500

5916 Chanteclair Dr 8, NAPLES

4 Beds 3 Baths 2,419 SqFt Rental MLS® # 226023811

Royal Shell Real Estate, Inc.

$19,500

↓ $3,000

740 Park Shore Dr, NAPLES

3 Beds 2 Baths 1,964 SqFt Rental MLS® # 226022312

John R Wood Properties

$19,500

2772 Tiburon Blvd E 5-102, NAPLES

3 Beds 4 Baths 2,950 SqFt Rental MLS® # 226005862

William Raveis Real Estate

$19,500

↓ $3,000

950 Galleon Dr, NAPLES

3 Beds 4 Baths 3,688 SqFt Rental MLS® # 226008476

Coastal Intl Properties LLC

$19,500

↓ $3,400

6849 Grenadier Blvd 105, NAPLES

3 Beds 3 Baths 1,900 SqFt Rental MLS® # 226005150

William Raveis Real Estate

$19,500

6849 Grenadier Blvd 1905, NAPLES

2 Beds 2 Baths 1,900 SqFt Rental MLS® # 225069819

Royal Shell Real Estate, Inc.

$19,000

248 4th Ave S D201, NAPLES

3 Beds 3 Baths 1,667 SqFt Rental MLS® # 2026028438

Gordon Pass Realty LLC

$19,000

822 105th Ave N, NAPLES

4 Beds 3 Baths 2,200 SqFt Rental MLS® # 226015108

Naples Vacation Properties

$19,000

↑ $500

6075 Pelican Bay Blvd 1105, NAPLES

3 Beds 3 Baths 2,333 SqFt Rental MLS® # 226010520

Premier Sotheby's Int'l Realty

$19,000

N/A, NAPLES

3 Beds 2 Baths 2,800 SqFt Rental MLS® # 226005294

Luxury Real Estate LLC

$19,000

10701 Gulf Shore Dr 701, NAPLES

2 Beds 3 Baths 1,803 SqFt Rental MLS® # 225075704

WeichertRealtors-ParadiseHomes

$18,900

9094 Sahalee Ct, NAPLES

4 Beds 4 Baths 3,726 SqFt Rental MLS® # 226006550

Downing Frye Realty Inc.

$18,500

640 2nd St S 2, NAPLES

2 Beds 3 Baths 2,168 SqFt Rental MLS® # 226023815

Royal Shell Real Estate, Inc.

$18,500

3296 Lookout Ln, NAPLES

3 Beds 3 Baths 2,647 SqFt Rental MLS® # 226017051

John R Wood Properties

$18,500

6075 Pelican Bay Blvd 605, NAPLES

3 Beds 3 Baths 2,333 SqFt Rental MLS® # 226012770

Premier Sotheby's Int'l Realty

$18,500

1035 3rd Ave S 411, NAPLES

3 Beds 3 Baths 2,264 SqFt Rental MLS® # 225080197

Royal Shell Real Estate, Inc.

$18,500

6810 Sand Pointe Cir 4.26, NAPLES

3 Beds 2 Baths 1,981 SqFt Rental MLS® # 225069822

Royal Shell Real Estate, Inc.

New New

$18,000

8838 Lely Island Cir, NAPLES

4 Beds 4 Baths 2,726 SqFt Rental MLS® # 226030105

Premier Sotheby's Int'l Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$20,000

4001 Gulf Shore Blvd N 707, NAPLES

$20,000

11002 Vanderbilt Dr, NAPLES

$20,000

4041 Gulf Shore Blvd N 1204, NAPLES

$20,000

5065 Kensington High St, NAPLES

$20,000

4901 Gulf Shore Blvd N 1604, NAPLES

$20,000

3722 Rachel Ln, NAPLES

$20,000

9470 Galliano Ter, NAPLES

$20,000

295 Grande Way 505, NAPLES

$20,000

8720 Bay Colony Dr 404, NAPLES

$19,500

N/A, NAPLES

$19,500

3423 Runaway Ct, NAPLES

$19,500

3440 Runaway Ln, NAPLES

$19,500

5916 Chanteclair Dr 8, NAPLES

$19,500

740 Park Shore Dr, NAPLES

$19,500

2772 Tiburon Blvd E 5-102, NAPLES

$19,500

950 Galleon Dr, NAPLES

$19,500

6849 Grenadier Blvd 105, NAPLES

$19,500

6849 Grenadier Blvd 1905, NAPLES

$19,000

248 4th Ave S D201, NAPLES

$19,000

822 105th Ave N, NAPLES

$19,000

6075 Pelican Bay Blvd 1105, NAPLES

$19,000

N/A, NAPLES

$19,000

10701 Gulf Shore Dr 701, NAPLES

$18,900

9094 Sahalee Ct, NAPLES

$18,500

640 2nd St S 2, NAPLES

$18,500

3296 Lookout Ln, NAPLES

$18,500

6075 Pelican Bay Blvd 605, NAPLES

$18,500

1035 3rd Ave S 411, NAPLES

$18,500

6810 Sand Pointe Cir 4.26, NAPLES

$18,000

8838 Lely Island Cir, NAPLES