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

$2,000

↓ $200

10349 Heritage Bay Blvd 2117, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226014778

Naples Breeze Realty

$2,000

315 Saint Andrews Blvd D38, NAPLES

2 Beds 2 Baths 1,126 SqFt Rental MLS® # 226024559

Premier Sotheby's Int'l Realty

$2,000

↓ $200

7731 Jewel Ln 204, NAPLES

3 Beds 2 Baths 1,199 SqFt Rental MLS® # 226025998

Realty One Group MVP

$2,000

1535 Chesapeake Ave A2, NAPLES

2 Beds 2 Baths 1,080 SqFt Rental MLS® # 226014903

Premiere Plus Realty Company

$1,999

9533 Avellino Way 2914, NAPLES

2 Beds 2 Baths 1,454 SqFt Rental MLS® # 226021463

Downing Frye Realty Inc.

$1,995

↓ $105

2700 Cypress Trace Cir 3134, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226023272

Keller Williams Realty Naples

$1,995

190 Turtle Lake Ct 311, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226009623

Downing Frye Realty Inc.

$1,950

↓ $50

1105 Reserve Ct 206, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226009966

Downing Frye Realty Inc.

$1,950

3001 Sandpiper Bay Cir B106, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226021556

Marzucco Real Estate

$1,950

N/A, NAPLES

2 Beds 2 Baths 1,129 SqFt Rental MLS® # 226019441

Fast Action Realty Inc

$1,950

1 Bluebill Ave 511, NAPLES

0 Beds 1 Bath 524 SqFt Rental MLS® # 226024408

Premiere Plus Realty Company

$1,900

↓ $50

1130 Partridge Cir 102, NAPLES

2 Beds 2 Baths 1,191 SqFt Rental MLS® # 226005253

Grice Realty Inc

$1,900

1275 Wildwood Lakes Blvd 2-108, NAPLES

2 Beds 1 Bath 909 SqFt Rental MLS® # 226022220

Realty One Group MVP

$1,890

6215 Wilshire Pines Cir 1601, NAPLES

3 Beds 2 Baths 1,592 SqFt Rental MLS® # 226010377

Downing Frye Realty Inc.

$1,875

1220 Wildwood Lakes Blvd 201, NAPLES

3 Beds 2 Baths 1,219 SqFt Rental MLS® # 226026558

Carrera Consulting Group Inter

$1,850

4210 Looking Glass Ln 4210, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 226029926

Waterfront Realty Group Inc

$1,850

↓ $140

5125 Cedar Springs Dr 204, NAPLES

3 Beds 2 Baths 2,177 SqFt Rental MLS® # 226014081

Downing Frye Realty Inc.

$1,850

↓ $550

4021 Ice Castle Way 4, NAPLES

2 Beds 2 Baths 1,246 SqFt Rental MLS® # 225078409

Downing Frye Realty Inc.

$1,850

1085 Forest Lakes Dr 8305, NAPLES

1 Bed 1 Bath 766 SqFt Rental MLS® # 226015333

Supreme Rental Solutions PM

$1,800

↓ $200

1083 Forest Lakes Dr 209, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226023642

Sun Realty

$1,800

573 Cape Florida Ln, NAPLES

3 Beds 2 Baths 1,488 SqFt Rental MLS® # 226018783

Realty One Group MVP

$1,800

201 Quail Forest Blvd 103, NAPLES

2 Beds 2 Baths 1,106 SqFt Rental MLS® # 226020349

Downing Frye Realty Inc.

$1,800

↓ $200

2855 Cypress Trace Cir 102, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226020197

Prime Real Estate of Naples

$1,800

1075 Foxfire Ln 201, NAPLES

2 Beds 1 Bath 843 SqFt Rental MLS® # 226022672

Realty One Group MVP

$1,790

↓ $100

1180 Reserve Way 302, NAPLES

1 Bed 1 Bath 850 SqFt Rental MLS® # 226012943

Realty Hub

$1,780

4625 Bayshore Dr D8, NAPLES

2 Beds 2 Baths 886 SqFt Rental MLS® # 226020789

Ivanova Realty LLC

$1,700

↓ $100

1010 Manatee Rd B304, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226006279

MDM Naples Real Estate LLC

$1,695

↓ $300

400 Forest Lakes Blvd 204, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226023755

Waterfront Realty Group Inc

$1,690

↓ $210

9554 Trevi Ct 4715, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226008372

Downing Frye Realty Inc.

$1,600

↓ $150

5515 Rattlesnake Hammock Rd 205, NAPLES

2 Beds 2 Baths 1,060 SqFt Rental MLS® # 226015767

ERA Naples Realty Services

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$2,000

10349 Heritage Bay Blvd 2117, NAPLES

$2,000

315 Saint Andrews Blvd D38, NAPLES

$2,000

7731 Jewel Ln 204, NAPLES

$2,000

1535 Chesapeake Ave A2, NAPLES

$1,999

9533 Avellino Way 2914, NAPLES

$1,995

2700 Cypress Trace Cir 3134, NAPLES

$1,995

190 Turtle Lake Ct 311, NAPLES

$1,950

1105 Reserve Ct 206, NAPLES

$1,950

3001 Sandpiper Bay Cir B106, NAPLES

$1,950

N/A, NAPLES

$1,950

1 Bluebill Ave 511, NAPLES

$1,900

1130 Partridge Cir 102, NAPLES

$1,900

1275 Wildwood Lakes Blvd 2-108, NAPLES

$1,890

6215 Wilshire Pines Cir 1601, NAPLES

$1,875

1220 Wildwood Lakes Blvd 201, NAPLES

$1,850

4210 Looking Glass Ln 4210, NAPLES

$1,850

5125 Cedar Springs Dr 204, NAPLES

$1,850

4021 Ice Castle Way 4, NAPLES

$1,850

1085 Forest Lakes Dr 8305, NAPLES

$1,800

1083 Forest Lakes Dr 209, NAPLES

$1,800

573 Cape Florida Ln, NAPLES

$1,800

201 Quail Forest Blvd 103, NAPLES

$1,800

2855 Cypress Trace Cir 102, NAPLES

$1,800

1075 Foxfire Ln 201, NAPLES

$1,790

1180 Reserve Way 302, NAPLES

$1,780

4625 Bayshore Dr D8, NAPLES

$1,700

1010 Manatee Rd B304, NAPLES

$1,695

400 Forest Lakes Blvd 204, NAPLES

$1,690

9554 Trevi Ct 4715, NAPLES

$1,600

5515 Rattlesnake Hammock Rd 205, NAPLES