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

$2,700

800 Augusta Blvd B201, NAPLES

3 Beds 2 Baths 1,294 SqFt Rental MLS® # 226028653

Marzucco Real Estate

$2,700

9735 Acqua Ct 621, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226018339

WeichertRealtors-ParadiseHomes

$2,700

800 Meadowland Dr H, NAPLES

2 Beds 3 Baths 1,432 SqFt Rental MLS® # 225080985

Coldwell Banker Realty

$2,650

2626 Seychelles Cir 1404, NAPLES

2 Beds 2 Baths 1,355 SqFt Rental MLS® # 226026131

John R Wood Properties

$2,650

↓ $100

9816 Giaveno Cir 1336, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226017297

Naples Vacation Properties

$2,600

280 Robin Hood Cir 101, NAPLES

3 Beds 2 Baths 1,413 SqFt Rental MLS® # 225080394

Waterfront Realty Group Inc

$2,600

8110 Calle Canovas St A, NAPLES

2 Beds 2 Baths 1,558 SqFt Rental MLS® # 226025714

REMAX Affinity Mercato

$2,600

2476 Orchid Bay Dr W201, NAPLES

3 Beds 2 Baths 1,928 SqFt Rental MLS® # 226002439

Downing Frye Realty Inc.

$2,600

6820 Beach Resort Dr 11, NAPLES

2 Beds 2 Baths 1,351 SqFt Rental MLS® # 226025713

DomainRealty.com LLC

New New

$2,500

5 Highpoint, NAPLES

2 Beds 2 Baths 1,100 SqFt Rental MLS® # 226031283

Sun Realty

$2,500

807 River Point Dr 304d, NAPLES

1 Bed 1 Bath 812 SqFt Rental MLS® # 226028903

Century 21 AllPoints Realty

$2,500

↓ $100

1160 Wildwood Lakes Blvd 9-206, NAPLES

2 Beds 2 Baths 1,042 SqFt Rental MLS® # 225080164

Realty One Group MVP

$2,500

53 High Point Cir W 304, NAPLES

2 Beds 2 Baths 1,015 SqFt Rental MLS® # 226004093

DomainRealty.com LLC

$2,500

105 Penny Ln 5, NAPLES

2 Beds 2 Baths 1,564 SqFt Rental MLS® # 226013293

Realty One Group MVP

$2,500

4603 Bayshore Dr F8, NAPLES

2 Beds 2 Baths 886 SqFt Rental MLS® # 226025277

Berkshire Hathaway FL Realty

$2,500

878 Meadowland Dr G, NAPLES

2 Beds 2 Baths 1,282 SqFt Rental MLS® # 226000881

Realty One Group MVP

$2,500

↓ $100

1295 Sweetwater Cv 8201, NAPLES

2 Beds 2 Baths 1,193 SqFt Rental MLS® # 226026834

AXEN Realty

$2,500

↓ $500

N/A, NAPLES

0 Beds 1 Bath 570 SqFt Rental MLS® # 225071819

SunStream Realty

$2,500

↑ $725

1808 Kings Lake Blvd 203, NAPLES

2 Beds 2 Baths 1,312 SqFt Rental MLS® # 226016223

Sun Realty

$2,500

1522 Mainsail Dr 4, NAPLES

2 Beds 2 Baths 966 SqFt Rental MLS® # 226028104

Epique Realty, INC

$2,500

9378 Pocida Ct 202, NAPLES

2 Beds 2 Baths 1,528 SqFt Rental MLS® # 226005485

Berkshire Hathaway FL Realty

$2,500

↓ $200

3021 Sandpiper Bay Cir E106, NAPLES

2 Beds 2 Baths 1,200 SqFt Rental MLS® # 2025011986

Palm Paradise Realty Group

$2,500

9596 Trevi Ct 5428, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226015886

Realty One Group MVP

$2,500

925 Palm View Dr 111, NAPLES

2 Beds 2 Baths 1,296 SqFt Rental MLS® # 226025684

DomainRealty.com LLC

$2,500

230 Sugar Pine Ln 230, NAPLES

2 Beds 2 Baths 1,311 SqFt Rental MLS® # 226029743

Parkline Realty

$2,500

1305 Mariposa Cir 1204, NAPLES

3 Beds 2 Baths 1,939 SqFt Rental MLS® # 226024557

Coldwell Banker Realty

$2,500

209 8th Ave S 209b, NAPLES

1 Bed 1 Bath 500 SqFt Rental MLS® # 226026017

William Raveis Real Estate

$2,495

N/A, NAPLES

2 Beds 2 Baths 1,203 SqFt Rental MLS® # 226021057

Fast Action Realty Inc

$2,450

138 Pebble Shores Dr 103, NAPLES

2 Beds 2 Baths 1,042 SqFt Rental MLS® # 225084850

Waterfront Realty Group Inc

$2,400

↓ $400

9727 Acqua Ct 434, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226022078

John R Wood Properties

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$2,700

800 Augusta Blvd B201, NAPLES

$2,700

9735 Acqua Ct 621, NAPLES

$2,700

800 Meadowland Dr H, NAPLES

$2,650

2626 Seychelles Cir 1404, NAPLES

$2,650

9816 Giaveno Cir 1336, NAPLES

$2,600

280 Robin Hood Cir 101, NAPLES

$2,600

8110 Calle Canovas St A, NAPLES

$2,600

2476 Orchid Bay Dr W201, NAPLES

$2,600

6820 Beach Resort Dr 11, NAPLES

$2,500

5 Highpoint, NAPLES

$2,500

807 River Point Dr 304d, NAPLES

$2,500

1160 Wildwood Lakes Blvd 9-206, NAPLES

$2,500

53 High Point Cir W 304, NAPLES

$2,500

105 Penny Ln 5, NAPLES

$2,500

4603 Bayshore Dr F8, NAPLES

$2,500

878 Meadowland Dr G, NAPLES

$2,500

1295 Sweetwater Cv 8201, NAPLES

$2,500

N/A, NAPLES

$2,500

1808 Kings Lake Blvd 203, NAPLES

$2,500

1522 Mainsail Dr 4, NAPLES

$2,500

9378 Pocida Ct 202, NAPLES

$2,500

3021 Sandpiper Bay Cir E106, NAPLES

$2,500

9596 Trevi Ct 5428, NAPLES

$2,500

925 Palm View Dr 111, NAPLES

$2,500

230 Sugar Pine Ln 230, NAPLES

$2,500

1305 Mariposa Cir 1204, NAPLES

$2,500

209 8th Ave S 209b, NAPLES

$2,495

N/A, NAPLES

$2,450

138 Pebble Shores Dr 103, NAPLES

$2,400

9727 Acqua Ct 434, NAPLES