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

$3,300

248 Bay Meadows Dr, NAPLES

2 Beds 2 Baths 1,582 SqFt Rental MLS® # 226031225

Coldwell Banker Realty

$3,250

1205 Wildwood Lakes Blvd 201, NAPLES

1 Bed 1 Bath 670 SqFt Rental MLS® # 226010865

Realty One Group MVP

$3,250

410 Bayfront Pl 2409, NAPLES

1 Bed 1 Bath 852 SqFt Rental MLS® # 226009815

Keller Williams Realty Naples

$3,200

400 Forest Lakes Blvd 310, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226019989

Berkshire Hathaway FL Realty

$3,200

953 Bunker Hill Dr, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226021802

KW Elevate Luxury

$3,200

300 Forest Lakes Blvd 201, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226012554

Downing Frye Realty Inc.

$3,200

200 Turtle Lake Ct 109, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226027138

Downing Frye Realty Inc.

$3,200

3057 Driftwood Way 4004, NAPLES

3 Beds 3 Baths 1,818 SqFt Rental MLS® # 226016775

John R Wood Properties

$3,200

4010 Ice Castle Way 7, NAPLES

2 Beds 2 Baths 1,314 SqFt Rental MLS® # 226008458

REMAX Affinity Mercato

$3,150

1010 Manatee Rd B304, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226028504

MDM Naples Real Estate LLC

$3,100

100 Forest Lakes Blvd 312, NAPLES

1 Bed 2 Baths 842 SqFt Rental MLS® # 225074202

Downing Frye Realty Inc.

$3,100

200 Forest Lakes Blvd 111, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 225082927

DomainRealty.com LLC

$3,100

170 Turtle Lake Ct 312, NAPLES

1 Bed 2 Baths 842 SqFt Rental MLS® # 225083204

Realty One Group MVP

$3,100

7943 Haven Dr 2, NAPLES

3 Beds 2 Baths 1,748 SqFt Rental MLS® # 226029350

Advantage Sales Of South FL

$3,000

175 Turtle Lake Ct 210, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226028516

DomainRealty.com LLC

$3,000

↓ $500

5857 Rattlesnake Hammock St 208, NAPLES

2 Beds 2 Baths 1,133 SqFt Rental MLS® # 225070303

Coastal Intl Properties LLC

$3,000

↓ $500

1157 Enbrook Loop, NAPLES

2 Beds 2 Baths 1,503 SqFt Rental MLS® # 225083531

Eister & Company, Inc

$3,000

1085 Forest Lakes Dr 8305, NAPLES

1 Bed 1 Bath 766 SqFt Rental MLS® # 226001532

Supreme Rental Solutions PM

$3,000

4525 Fluvia Ave, NAPLES

2 Beds 1 Bath 1,050 SqFt Rental MLS® # 226015623

John R Wood Properties

$3,000

3595 Laurel Greens Ln N 103, NAPLES

2 Beds 2 Baths 1,652 SqFt Rental MLS® # 226023213

West Shore Properties RE,MNGT

$3,000

6960 Avalon Cir 807, NAPLES

3 Beds 2 Baths 1,725 SqFt Rental MLS® # 226024976

WeichertRealtors-ParadiseHomes

New New

$3,000

4680 Hawks Nest Way D-103, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226031322

John R Wood Properties

$3,000

3703 Exuma Way, NAPLES

2 Beds 2 Baths 1,680 SqFt Rental MLS® # 226012795

Islandwalk Properties, LLC

448 Gabriel Cir #3310 Gabriel Cir 3310, NAPLES

$3,000

↓ $500

448 Gabriel Cir #3310 Gabriel Cir 3310, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 225082023

Downing Frye Realty Inc.

$3,000

820 Meadowland Dr D, NAPLES

2 Beds 3 Baths 1,432 SqFt Rental MLS® # 225083562

Realty One Group MVP

$3,000

2972 Kings Lake Blvd 2972, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 225074480

Waterfront Realty Group Inc

$3,000

450 Launch Cir 404, NAPLES

3 Beds 2 Baths 1,635 SqFt Rental MLS® # 226018428

William Raveis Real Estate

$3,000

↓ $400

1860 Bald Eagle Dr 403b, NAPLES

2 Beds 2 Baths 1,325 SqFt Rental MLS® # 225085034

Naples Realty & Property Mgmt

$3,000

473 12th Ave S B12, NAPLES

1 Bed 1 Bath 600 SqFt Rental MLS® # 226018694

Premiere Plus Realty Company

$3,000

470 Launch Cir V-604, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226018434

William Raveis Real Estate

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$3,300

248 Bay Meadows Dr, NAPLES

$3,250

1205 Wildwood Lakes Blvd 201, NAPLES

$3,250

410 Bayfront Pl 2409, NAPLES

$3,200

400 Forest Lakes Blvd 310, NAPLES

$3,200

953 Bunker Hill Dr, NAPLES

$3,200

300 Forest Lakes Blvd 201, NAPLES

$3,200

200 Turtle Lake Ct 109, NAPLES

$3,200

3057 Driftwood Way 4004, NAPLES

$3,200

4010 Ice Castle Way 7, NAPLES

$3,150

1010 Manatee Rd B304, NAPLES

$3,100

100 Forest Lakes Blvd 312, NAPLES

$3,100

200 Forest Lakes Blvd 111, NAPLES

$3,100

170 Turtle Lake Ct 312, NAPLES

$3,100

7943 Haven Dr 2, NAPLES

$3,000

175 Turtle Lake Ct 210, NAPLES

$3,000

5857 Rattlesnake Hammock St 208, NAPLES

$3,000

1157 Enbrook Loop, NAPLES

$3,000

1085 Forest Lakes Dr 8305, NAPLES

$3,000

4525 Fluvia Ave, NAPLES

$3,000

3595 Laurel Greens Ln N 103, NAPLES

$3,000

6960 Avalon Cir 807, NAPLES

$3,000

4680 Hawks Nest Way D-103, NAPLES

$3,000

3703 Exuma Way, NAPLES

$3,000

448 Gabriel Cir #3310 Gabriel Cir 3310, NAPLES

$3,000

820 Meadowland Dr D, NAPLES

$3,000

2972 Kings Lake Blvd 2972, NAPLES

$3,000

450 Launch Cir 404, NAPLES

$3,000

1860 Bald Eagle Dr 403b, NAPLES

$3,000

473 12th Ave S B12, NAPLES

$3,000

470 Launch Cir V-604, NAPLES