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

New New

$35,000

2211 Kingfish Rd, NAPLES

4 Beds 4 Baths 2,667 SqFt Rental MLS® # 226030855

Naples Vacation Properties

$35,000

1427 Hemingway Pl, NAPLES

4 Beds 5 Baths 4,067 SqFt Rental MLS® # 226020357

William Raveis Real Estate

$35,000

13915 Old Coast Rd 502, NAPLES

3 Beds 4 Baths 3,280 SqFt Rental MLS® # 226019620

William Raveis Real Estate

$35,000

↑ $5,000

476 1st Ave N, NAPLES

4 Beds 4 Baths 2,700 SqFt Rental MLS® # 226001787

Royal Shell Real Estate, Inc.

$35,000

↑ $13,000

370 6th Ave S, NAPLES

4 Beds 3 Baths 2,488 SqFt Rental MLS® # 225080735

Naples Trust Real Estate Servi

$35,000

↑ $5,000

6597 Nicholas Blvd 705, NAPLES

3 Beds 3 Baths 2,700 SqFt Rental MLS® # 225077838

William Raveis Real Estate

$35,000

1060 Galleon Dr, NAPLES

3 Beds 3 Baths 3,589 SqFt Rental MLS® # 225069104

Douglas Elliman Florida,LLC

$34,500

1627 Murex Ln, NAPLES

4 Beds 3 Baths 2,448 SqFt Rental MLS® # 226018152

Compass Florida LLC

$34,000

161 Mahogany Dr, NAPLES

4 Beds 4 Baths 2,387 SqFt Rental MLS® # 226029540

Compass Florida LLC

$34,000

4400 Gulf Shore Blvd N 3-305, NAPLES

4 Beds 5 Baths 4,079 SqFt Rental MLS® # 225076304

John R Wood Properties

$33,000

677 18th Ave S, NAPLES

3 Beds 3 Baths 2,705 SqFt Rental MLS® # 225073551

Berkshire Hathaway FL Realty

$31,000

4051 Gulf Shore Blvd N 105, NAPLES

3 Beds 2 Baths 2,152 SqFt Rental MLS® # 226027593

William Raveis Real Estate

New New

$30,000

860 7th St S, NAPLES

3 Beds 2 Baths 2,358 SqFt Rental MLS® # 226030194

Premier Sotheby's Int'l Realty

$30,000

5550 Heron Point Dr 903, NAPLES

2 Beds 2 Baths 1,263 SqFt Rental MLS® # 226028002

Downing Frye Realty Inc.

$30,000

403 Seabee Ave, NAPLES

5 Beds 5 Baths 4,815 SqFt Rental MLS® # 226026209

Florida Prime Realty, LLC

$30,000

9856 Corso Bello Dr, NAPLES

4 Beds 5 Baths 3,542 SqFt Rental MLS® # 226022647

Naples Vacation Properties

$30,000

↓ $5,000

444 2nd Ave N, NAPLES

3 Beds 3 Baths 2,776 SqFt Rental MLS® # 226018241

William Raveis Real Estate

$30,000

159 Conners Ave, NAPLES

4 Beds 3 Baths 3,034 SqFt Rental MLS® # 226017546

WeichertRealtors-ParadiseHomes

$30,000

295 6th St N, NAPLES

3 Beds 3 Baths 1,868 SqFt Rental MLS® # 226014899

William Raveis Real Estate

$30,000

9517 Gulf Shore Dr 401, NAPLES

3 Beds 4 Baths 2,230 SqFt Rental MLS® # 226015587

Keller Williams Realty Naples

$30,000

↓ $10,000

2052 Isla Vista Ln, NAPLES

4 Beds 6 Baths 4,869 SqFt Rental MLS® # 226011358

Premier Sotheby's Int'l Realty

$30,000

↑ $29,970

4021 Gulf Shore Blvd N 1804, NAPLES

3 Beds 3 Baths 2,500 SqFt Rental MLS® # 225084706

Royal Shell Real Estate, Inc.

$30,000

359 2nd Ave N, NAPLES

3 Beds 3 Baths 2,252 SqFt Rental MLS® # 225080202

Royal Shell Real Estate, Inc.

$30,000

711 91st Ave N, NAPLES

6 Beds 3 Baths 3,246 SqFt Rental MLS® # 225077711

Naples Vibe Realty, LLC

$30,000

271 1st Ave S, NAPLES

3 Beds 3 Baths 1,930 SqFt Rental MLS® # 225075501

John R Wood Properties

$30,000

7117 Pelican Bay Blvd 1101, NAPLES

3 Beds 3 Baths 2,500 SqFt Rental MLS® # 225073987

Premier Sotheby's Int'l Realty

$30,000

↑ $10,000

877 7th St S, NAPLES

3 Beds 3 Baths 1,900 SqFt Rental MLS® # 225072191

Naples Homes and Rentals Inc

$29,000

↓ $6,000

535 Anchor Rode Dr, NAPLES

4 Beds 3 Baths 2,422 SqFt Rental MLS® # 225083789

Naples Vacation Properties

$28,000

2201 Beacon Ln, NAPLES

3 Beds 3 Baths 2,867 SqFt Rental MLS® # 226018596

Douglas Elliman Florida,LLC

$28,000

16659 Pistoia Way, NAPLES

4 Beds 5 Baths 3,698 SqFt Rental MLS® # 226012091

Real Broker, LLC

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$35,000

2211 Kingfish Rd, NAPLES

$35,000

1427 Hemingway Pl, NAPLES

$35,000

13915 Old Coast Rd 502, NAPLES

$35,000

476 1st Ave N, NAPLES

$35,000

370 6th Ave S, NAPLES

$35,000

6597 Nicholas Blvd 705, NAPLES

$35,000

1060 Galleon Dr, NAPLES

$34,500

1627 Murex Ln, NAPLES

$34,000

161 Mahogany Dr, NAPLES

$34,000

4400 Gulf Shore Blvd N 3-305, NAPLES

$33,000

677 18th Ave S, NAPLES

$31,000

4051 Gulf Shore Blvd N 105, NAPLES

$30,000

860 7th St S, NAPLES

$30,000

5550 Heron Point Dr 903, NAPLES

$30,000

403 Seabee Ave, NAPLES

$30,000

9856 Corso Bello Dr, NAPLES

$30,000

444 2nd Ave N, NAPLES

$30,000

159 Conners Ave, NAPLES

$30,000

295 6th St N, NAPLES

$30,000

9517 Gulf Shore Dr 401, NAPLES

$30,000

2052 Isla Vista Ln, NAPLES

$30,000

4021 Gulf Shore Blvd N 1804, NAPLES

$30,000

359 2nd Ave N, NAPLES

$30,000

711 91st Ave N, NAPLES

$30,000

271 1st Ave S, NAPLES

$30,000

7117 Pelican Bay Blvd 1101, NAPLES

$30,000

877 7th St S, NAPLES

$29,000

535 Anchor Rode Dr, NAPLES

$28,000

2201 Beacon Ln, NAPLES

$28,000

16659 Pistoia Way, NAPLES