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

$8,500

714 Reef Point Cir, NAPLES

2 Beds 2 Baths 1,347 SqFt Rental MLS® # 226012519

Coldwell Banker Realty

$8,500

15 Bluebill Ave 805, NAPLES

2 Beds 2 Baths 1,525 SqFt Rental MLS® # 226015848

Realty One Group MVP

$8,500

7046 Barrington Cir 202, NAPLES

2 Beds 2 Baths 1,663 SqFt Rental MLS® # 226019973

Berkshire Hathaway FL Realty

$8,500

10420 Gulf Shore Dr 162, NAPLES

1 Bed 1 Bath 1,045 SqFt Rental MLS® # 226016523

SunStream Realty

$8,500

↓ $450

13435 Silktail Dr, NAPLES

2 Beds 2 Baths 1,837 SqFt Rental MLS® # 226018362

Premier Sotheby's Int'l Realty

$8,500

792 108th Ave N, NAPLES

3 Beds 2 Baths 1,446 SqFt Rental MLS® # 226017980

LPT Realty,LLC

$8,500

6545 Chestnut Cir, NAPLES

2 Beds 2 Baths 2,322 SqFt Rental MLS® # 226014445

Coldwell Banker Realty

$8,500

981 8th Ter N, NAPLES

3 Beds 2 Baths 1,200 SqFt Rental MLS® # 225083315

John R Wood Properties

$8,500

16382 Viansa Way 3-102, NAPLES

3 Beds 4 Baths 2,400 SqFt Rental MLS® # 225077712

Real Estate Specialty Svcs II

$8,500

↓ $500

7755 Martino Cir, NAPLES

3 Beds 3 Baths 2,244 SqFt Rental MLS® # 226011764

DomainRealty.com LLC

$8,500

14488 Stillwater Way, NAPLES

3 Beds 2 Baths 1,830 SqFt Rental MLS® # 226003112

John R Wood Properties

$8,500

2991 2nd St Nw, NAPLES

3 Beds 2 Baths 1,997 SqFt Rental MLS® # 226003938

Keller Williams Elite Realty

$8,500

7108 Barrington Cir 101, NAPLES

2 Beds 2 Baths 1,527 SqFt Rental MLS® # 225083070

Downing Frye Realty Inc.

$8,500

6561 Dominica Dr 8-101, NAPLES

3 Beds 3 Baths 2,214 SqFt Rental MLS® # 225081130

John R Wood Properties

$8,500

1351 Curlew Ave 104, NAPLES

2 Beds 2 Baths 1,022 SqFt Rental MLS® # 225080011

Marzucco Real Estate

$8,500

15177 Butler Lake Dr 201, NAPLES

3 Beds 2 Baths 2,152 SqFt Rental MLS® # 225077783

DomainRealty.com LLC

$8,500

↓ $500

167 Torrey Pines Pt, NAPLES

3 Beds 2 Baths 1,907 SqFt Rental MLS® # 225075027

John R Wood Properties

$8,500

800 L Ambiance Cir 106, NAPLES

3 Beds 2 Baths 1,620 SqFt Rental MLS® # 225075191

My Florida Real Estate, LLC

$8,500

↑ $500

N/A, NAPLES

2 Beds 2 Baths 1,215 SqFt Rental MLS® # 225061939

Luxe Naples Real Estate

$8,500

↓ $1,500

4560 Gulf Shore Blvd N 3-213, NAPLES

2 Beds 2 Baths 1,321 SqFt Rental MLS® # 225072881

Premier Sotheby's Int'l Realty

$8,500

2371 Ravenna Blvd 101, NAPLES

3 Beds 2 Baths 1,619 SqFt Rental MLS® # 225070812

Compass Florida LLC

$8,500

613 Beachwalk Cir J-204, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 225071602

Realty One Group MVP

$8,500

2444 Ravenna Blvd 202, NAPLES

3 Beds 3 Baths 2,015 SqFt Rental MLS® # 225069808

Royal Shell Real Estate, Inc.

$8,500

859 Tanbark Dr 205, NAPLES

2 Beds 2 Baths 1,203 SqFt Rental MLS® # 225058183

John R Wood Properties

$8,400

1570 Winding Oaks Way 201, NAPLES

3 Beds 2 Baths 2,182 SqFt Rental MLS® # 226020053

SunStream Realty

$8,325

7832 Hawthorne Dr 1901, NAPLES

2 Beds 2 Baths 1,880 SqFt Rental MLS® # 2026006754

Coldwell Banker Realty

New New

$8,000

10686 Gulf Shore Dr 206, NAPLES

2 Beds 2 Baths 1,490 SqFt Rental MLS® # 226030856

Royal Shell Real Estate, Inc.

$8,000

1100 8th Ave S H227, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226028740

William Raveis Real Estate

$8,000

589 Beachwalk Cir P-203, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226028711

Gulf Breeze Real Estate LC

$8,000

5870 Three Iron Drive 4-401, NAPLES

3 Beds 2 Baths 1,633 SqFt Rental MLS® # 226025140

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$8,500

714 Reef Point Cir, NAPLES

$8,500

15 Bluebill Ave 805, NAPLES

$8,500

7046 Barrington Cir 202, NAPLES

$8,500

10420 Gulf Shore Dr 162, NAPLES

$8,500

13435 Silktail Dr, NAPLES

$8,500

792 108th Ave N, NAPLES

$8,500

6545 Chestnut Cir, NAPLES

$8,500

981 8th Ter N, NAPLES

$8,500

16382 Viansa Way 3-102, NAPLES

$8,500

7755 Martino Cir, NAPLES

$8,500

14488 Stillwater Way, NAPLES

$8,500

2991 2nd St Nw, NAPLES

$8,500

7108 Barrington Cir 101, NAPLES

$8,500

6561 Dominica Dr 8-101, NAPLES

$8,500

1351 Curlew Ave 104, NAPLES

$8,500

15177 Butler Lake Dr 201, NAPLES

$8,500

167 Torrey Pines Pt, NAPLES

$8,500

800 L Ambiance Cir 106, NAPLES

$8,500

N/A, NAPLES

$8,500

4560 Gulf Shore Blvd N 3-213, NAPLES

$8,500

2371 Ravenna Blvd 101, NAPLES

$8,500

613 Beachwalk Cir J-204, NAPLES

$8,500

2444 Ravenna Blvd 202, NAPLES

$8,500

859 Tanbark Dr 205, NAPLES

$8,400

1570 Winding Oaks Way 201, NAPLES

$8,325

7832 Hawthorne Dr 1901, NAPLES

$8,000

10686 Gulf Shore Dr 206, NAPLES

$8,000

1100 8th Ave S H227, NAPLES

$8,000

589 Beachwalk Cir P-203, NAPLES

$8,000

5870 Three Iron Drive 4-401, NAPLES