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

$5,000

↑ $750

7615 Arbor Lakes Ct 413, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225082009

Naples Trust Real Estate Servi

$5,000

1937 Crestview Way 171, NAPLES

3 Beds 2 Baths 2,050 SqFt Rental MLS® # 226025440

KW Elevate Luxury

$5,000

8500 Mystic Greens Way 5-505, NAPLES

3 Beds 3 Baths 2,396 SqFt Rental MLS® # 226000816

WeichertRealtors-ParadiseHomes

$5,000

↓ $1,000

801 River Point Dr 303a, NAPLES

1 Bed 1 Bath 815 SqFt Rental MLS® # 226011110

Royal Shell Real Estate, Inc.

$5,000

3029 Driftwood Way 3307, NAPLES

3 Beds 2 Baths 1,383 SqFt Rental MLS® # 226028538

Coldwell Banker Realty

$5,000

11 Bluebill Ave 103, NAPLES

1 Bed 1 Bath 780 SqFt Rental MLS® # 226029187

Royal Shell Real Estate, Inc.

$5,000

6687 Huntley Ln S, NAPLES

4 Beds 3 Baths 2,398 SqFt Rental MLS® # 226001640

Waterfront Realty Group Inc

$5,000

↓ $250

12832 Brynwood Way, NAPLES

3 Beds 2 Baths 1,714 SqFt Rental MLS® # 226021982

Realty One Group MVP

$5,000

3 Bluebill Ave 704, NAPLES

1 Bed 1 Bath 807 SqFt Rental MLS® # 226005165

William Raveis Real Estate

$5,000

75 Emerald Woods Dr G2, NAPLES

2 Beds 3 Baths 1,360 SqFt Rental MLS® # 226022540

ALL IN PROPERTY MANAGEMENT LLC

$5,000

1250 Yesica Ann Cir E102, NAPLES

2 Beds 2 Baths 1,168 SqFt Rental MLS® # 226013165

Berkshire Hathaway FL Realty

$5,000

↑ $3,000

2730 Cypress Trace Cir 2836s, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226003437

REMAX Affinity Mercato

$5,000

↑ $2,000

2730 Cypress Trace Cir 2826, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226003446

REMAX Affinity Mercato

$5,000

↓ $200

3320 W Crown Pointe Blvd 201, NAPLES

3 Beds 2 Baths 1,630 SqFt Rental MLS® # 226023365

John R Wood Properties

$5,000

780 10th Ave S 22, NAPLES

1 Bed 1 Bath 566 SqFt Rental MLS® # 225082724

William Raveis Real Estate

$5,000

9104 Cherry Oaks Trl, NAPLES

3 Beds 2 Baths 1,876 SqFt Rental MLS® # 225082804

Premiere Plus Realty Company

$5,000

2740 Cypress Trace Cir 2733, NAPLES

2 Beds 2 Baths 1,197 SqFt Rental MLS® # 226003444

REMAX Affinity Mercato

$5,000

7098 Pond Cypress Ct 102, NAPLES

2 Beds 2 Baths 1,488 SqFt Rental MLS® # 226025907

John R Wood Properties

$5,000

8161 Twelve Oaks Cir 512, NAPLES

2 Beds 2 Baths 1,066 SqFt Rental MLS® # 226014304

Realty One Group MVP

$5,000

↓ $5,000

1417 Foxfire Ln, NAPLES

3 Beds 2 Baths 1,970 SqFt Rental MLS® # 226016616

Realty One Group MVP

$5,000

195 Peppermint Ln W 881, NAPLES

2 Beds 2 Baths 1,335 SqFt Rental MLS® # 226020365

Downing Frye Realty Inc.

$5,000

↑ $1,000

5595 Greenwood Cir 92, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 225081684

Realty One Group MVP

$5,000

15145 Palmer Lake Cir 103, NAPLES

3 Beds 2 Baths 1,571 SqFt Rental MLS® # 226029611

Premier Sotheby's Int'l Realty

$5,000

14537 Stern Way, NAPLES

4 Beds 2 Baths 2,034 SqFt Rental MLS® # 226019085

Compass Florida LLC

$5,000

4821 Europa Dr, NAPLES

3 Beds 2 Baths 1,605 SqFt Rental MLS® # 226023914

Naples Trust Real Estate Servi

New New

$5,000

9115 Strada Pl 5211, NAPLES

2 Beds 2 Baths 1,435 SqFt Rental MLS® # 226030713

Berkshire Hathaway FL Realty

$5,000

↓ $500

6325 Wilshire Pines Cir 308, NAPLES

3 Beds 2 Baths 1,577 SqFt Rental MLS® # 225073755

Real Broker, LLC

$5,000

2730 Cypress Trace Cir 2828, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 225083456

Exp Realty LLC

$5,000

2820 Cypress Trace Cir 2023, NAPLES

2 Beds 2 Baths 1,094 SqFt Rental MLS® # 226018231

Keller Williams Realty Naples

$5,000

13441 Coronado Dr, NAPLES

3 Beds 2 Baths 1,837 SqFt Rental MLS® # 226012232

John R Wood Properties

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,000

7615 Arbor Lakes Ct 413, NAPLES

$5,000

1937 Crestview Way 171, NAPLES

$5,000

8500 Mystic Greens Way 5-505, NAPLES

$5,000

801 River Point Dr 303a, NAPLES

$5,000

3029 Driftwood Way 3307, NAPLES

$5,000

11 Bluebill Ave 103, NAPLES

$5,000

6687 Huntley Ln S, NAPLES

$5,000

12832 Brynwood Way, NAPLES

$5,000

3 Bluebill Ave 704, NAPLES

$5,000

75 Emerald Woods Dr G2, NAPLES

$5,000

1250 Yesica Ann Cir E102, NAPLES

$5,000

2730 Cypress Trace Cir 2836s, NAPLES

$5,000

2730 Cypress Trace Cir 2826, NAPLES

$5,000

3320 W Crown Pointe Blvd 201, NAPLES

$5,000

780 10th Ave S 22, NAPLES

$5,000

9104 Cherry Oaks Trl, NAPLES

$5,000

2740 Cypress Trace Cir 2733, NAPLES

$5,000

7098 Pond Cypress Ct 102, NAPLES

$5,000

8161 Twelve Oaks Cir 512, NAPLES

$5,000

1417 Foxfire Ln, NAPLES

$5,000

195 Peppermint Ln W 881, NAPLES

$5,000

5595 Greenwood Cir 92, NAPLES

$5,000

15145 Palmer Lake Cir 103, NAPLES

$5,000

14537 Stern Way, NAPLES

$5,000

4821 Europa Dr, NAPLES

$5,000

9115 Strada Pl 5211, NAPLES

$5,000

6325 Wilshire Pines Cir 308, NAPLES

$5,000

2730 Cypress Trace Cir 2828, NAPLES

$5,000

2820 Cypress Trace Cir 2023, NAPLES

$5,000

13441 Coronado Dr, NAPLES