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

$5,200

↑ $200

6816 Satinleaf Rd S 102, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 226015248

SunStream Realty

$5,200

1912 Tarpon Bay Dr N, NAPLES

2 Beds 2 Baths 1,566 SqFt Rental MLS® # 226021128

SunStream Realty

$5,200

↓ $300

2815 Cypress Trace Cir 2-101, NAPLES

2 Beds 2 Baths 1,252 SqFt Rental MLS® # 226002897

West Shore Properties RE,MNGT

$5,200

6934 Rain Lily Ct 103, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 225064725

SunStream Realty

$5,200

83 Glades Blvd 3, NAPLES

2 Beds 2 Baths 1,204 SqFt Rental MLS® # 226001022

Napoli Realty Services, LLC

$5,200

3060 Horizon Ln 1404, NAPLES

3 Beds 3 Baths 1,818 SqFt Rental MLS® # 226025685

Naples Flat Fee Realty LLC

$5,200

159 Teryl Rd 2, NAPLES

2 Beds 2 Baths 1,080 SqFt Rental MLS® # 226007507

Napoli Realty Services, LLC

$5,100

3685 Amberly Cir W D305, NAPLES

2 Beds 2 Baths 1,320 SqFt Rental MLS® # 225073198

Napoli Realty Services, LLC

$5,100

↑ $600

3051 Horizon Ln 1803, NAPLES

2 Beds 2 Baths 1,482 SqFt Rental MLS® # 226001970

Prime Real Estate of Naples

$5,000

228 Belina Dr 604, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 226023443

Naples Vibe Realty, LLC

$5,000

2860 Citrus Lake Dr R-202, NAPLES

3 Beds 2 Baths 1,590 SqFt Rental MLS® # 226020813

Downing Frye Realty Inc.

$5,000

2021 Crestview Way 113, NAPLES

3 Beds 2 Baths 1,634 SqFt Rental MLS® # 226011192

Grice Realty Inc

$5,000

4556 Andover Way E104, NAPLES

2 Beds 2 Baths 1,072 SqFt Rental MLS® # 225077301

Waterfront Realty Group Inc

$5,000

2400 Bayou Ln 7506, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 226019724

Downing Frye Realty Inc.

$5,000

540 4th Ave S 13, NAPLES

1 Bed 1 Bath 580 SqFt Rental MLS® # 225076327

John R Wood Properties

$5,000

4607 Arboretum Cir 103, NAPLES

2 Beds 2 Baths 1,406 SqFt Rental MLS® # 226004842

Naples Flat Fee Realty LLC

New New

$5,000

1363 Woodridge Ave, NAPLES

3 Beds 2 Baths 1,577 SqFt Rental MLS® # 226030488

Downing Frye Realty Inc.

$5,000

↓ $500

9731 Acqua Ct 533, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226004922

DomainRealty.com LLC

$5,000

348 Tern Dr 4, NAPLES

2 Beds 2 Baths 1,270 SqFt Rental MLS® # 226022253

Napoli Realty Services, LLC

$5,000

577 Beachwalk Cir R202, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226010241

Realty One Group MVP

$5,000

1520 Imperial Golf Course Blvd 211, NAPLES

2 Beds 2 Baths 1,357 SqFt Rental MLS® # 226019992

Berkshire Hathaway FL Realty

$5,000

15 Bluebill Ave 805, NAPLES

2 Beds 2 Baths 1,525 SqFt Rental MLS® # 226000342

Realty One Group MVP

$5,000

6817 Sterling Greens Dr 102, NAPLES

3 Beds 2 Baths 1,499 SqFt Rental MLS® # 226027421

KW Elevate Luxury

$5,000

5045 Cedar Springs Dr 103, NAPLES

2 Beds 2 Baths 1,202 SqFt Rental MLS® # 226019659

William Raveis Real Estate

New New

$5,000

1100 Gulf Shore Blvd N 207, NAPLES

2 Beds 2 Baths 940 SqFt Rental MLS® # 226030913

Premier Sotheby's Int'l Realty

$5,000

788 Park Shore Dr B22, NAPLES

2 Beds 2 Baths 1,015 SqFt Rental MLS® # 226005499

Coldwell Banker Realty

$5,000

6954 Avalon Cir 702, NAPLES

2 Beds 2 Baths 1,467 SqFt Rental MLS® # 226026595

Waterfront Realty Group Inc

$5,000

3555 Laurel Greens Ln N 202, NAPLES

2 Beds 2 Baths 1,784 SqFt Rental MLS® # 226011660

Palm Realty Group

$5,000

↓ $500

3308 Europa Dr 30, NAPLES

2 Beds 2 Baths 1,205 SqFt Rental MLS® # 225080282

Premier Sotheby's Int'l Realty

$5,000

1420 Sweetwater Cv 102, NAPLES

2 Beds 2 Baths 1,279 SqFt Rental MLS® # 226021159

Coldwell Banker Realty

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,200

6816 Satinleaf Rd S 102, NAPLES

$5,200

1912 Tarpon Bay Dr N, NAPLES

$5,200

2815 Cypress Trace Cir 2-101, NAPLES

$5,200

6934 Rain Lily Ct 103, NAPLES

$5,200

83 Glades Blvd 3, NAPLES

$5,200

3060 Horizon Ln 1404, NAPLES

$5,200

159 Teryl Rd 2, NAPLES

$5,100

3685 Amberly Cir W D305, NAPLES

$5,100

3051 Horizon Ln 1803, NAPLES

$5,000

228 Belina Dr 604, NAPLES

$5,000

2860 Citrus Lake Dr R-202, NAPLES

$5,000

2021 Crestview Way 113, NAPLES

$5,000

4556 Andover Way E104, NAPLES

$5,000

2400 Bayou Ln 7506, NAPLES

$5,000

540 4th Ave S 13, NAPLES

$5,000

4607 Arboretum Cir 103, NAPLES

$5,000

1363 Woodridge Ave, NAPLES

$5,000

9731 Acqua Ct 533, NAPLES

$5,000

348 Tern Dr 4, NAPLES

$5,000

577 Beachwalk Cir R202, NAPLES

$5,000

1520 Imperial Golf Course Blvd 211, NAPLES

$5,000

15 Bluebill Ave 805, NAPLES

$5,000

6817 Sterling Greens Dr 102, NAPLES

$5,000

5045 Cedar Springs Dr 103, NAPLES

$5,000

1100 Gulf Shore Blvd N 207, NAPLES

$5,000

788 Park Shore Dr B22, NAPLES

$5,000

6954 Avalon Cir 702, NAPLES

$5,000

3555 Laurel Greens Ln N 202, NAPLES

$5,000

3308 Europa Dr 30, NAPLES

$5,000

1420 Sweetwater Cv 102, NAPLES