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

$2,400

↓ $250

154 Cypress Way E 1102, NAPLES

3 Beds 2 Baths 1,150 SqFt Rental MLS® # 226012773

John R Wood Properties

$2,395

5 High Point Cir W 104, NAPLES

2 Beds 2 Baths 871 SqFt Rental MLS® # 226029644

Downing Frye Realty Inc.

$2,350

150 Round Key Cir G-15, NAPLES

2 Beds 2 Baths 1,222 SqFt Rental MLS® # 226030491

Naples Vibe Realty, LLC

$2,350

135 Cypress Way E C, NAPLES

2 Beds 2 Baths 1,377 SqFt Rental MLS® # 226021581

Realty One Group MVP

$2,300

↓ $500

3298 Megan Ln 2, NAPLES

3 Beds 3 Baths 1,437 SqFt Rental MLS® # 226025056

Waterfront Realty Group Inc

$2,300

↓ $550

4187 Lakewood Blvd E13, NAPLES

2 Beds 1 Bath 1,051 SqFt Rental MLS® # 226014325

Waterfront Realty Group Inc

$2,300

↓ $2,600

1120 Sarah Jean Cir B205, NAPLES

3 Beds 2 Baths 1,370 SqFt Rental MLS® # 226015423

Florida Realty & Mgmt Services

$2,300

↓ $600

1190 Reserve Way 304, NAPLES

2 Beds 2 Baths 1,059 SqFt Rental MLS® # 226010644

Downing Frye Realty Inc.

$2,300

2860 Citrus Lake Dr R-202, NAPLES

3 Beds 2 Baths 1,590 SqFt Rental MLS® # 226027169

Downing Frye Realty Inc.

$2,300

7360 Glenmoor Ln 4301, NAPLES

2 Beds 2 Baths 954 SqFt Rental MLS® # 226005052

William Raveis Real Estate

$2,300

↓ $200

1700 Windy Pines Dr 1701, NAPLES

2 Beds 2 Baths 1,349 SqFt Rental MLS® # 225084881

Marzucco Real Estate

$2,300

112 Bob O Link Way B, NAPLES

2 Beds 2 Baths 1,235 SqFt Rental MLS® # 226025421

Coldwell Banker Realty

$2,300

37 High Point Cir E 305, NAPLES

2 Beds 2 Baths 1,015 SqFt Rental MLS® # 226029614

Downing Frye Realty Inc.

New New

$2,295

3370 10th St N 1304, NAPLES

2 Beds 2 Baths 1,186 SqFt Rental MLS® # 226025715

Current Property Management

$2,250

15171 Cedarwood Ln 3604, NAPLES

2 Beds 2 Baths 1,267 SqFt Rental MLS® # 226022703

Downing Frye Realty Inc.

$2,250

106 Siena Way 1508, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226008368

Downing Frye Realty Inc.

$2,225

↓ $10

5928 Cranbrook Way D202, NAPLES

2 Beds 2 Baths 1,318 SqFt Rental MLS® # 226024335

Excel Real Estate Services Inc

$2,200

↓ $195

1086 Forest Lakes Dr 303, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 226017688

Century 21 AllPoints Realty

$2,200

↑ $500

3323 Olympic Dr 716, NAPLES

2 Beds 2 Baths 965 SqFt Rental MLS® # 226013585

Downing Frye Realty Inc.

$2,200

2865 Cypress Trace Cir 203, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226018427

Palm Realty Group

$2,195

↓ $200

8680 Cedar Hammock Cir 116, NAPLES

2 Beds 2 Baths 1,232 SqFt Rental MLS® # 226015982

Premier Property Management

$2,175

9521 Avellino Way 2415, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226022479

Realty One Group MVP

$2,150

1315 Mainsail Dr 1115, NAPLES

2 Beds 2 Baths 843 SqFt Rental MLS® # 225082966

Re/Max Alliance Group

$2,100

↓ $300

1950 W Crown Pointe Blvd B106, NAPLES

2 Beds 2 Baths 1,129 SqFt Rental MLS® # 225069215

Premiere Plus Realty Company

$2,050

↓ $200

1645 Spoonbill Ln C, NAPLES

2 Beds 2 Baths 1,350 SqFt Rental MLS® # 226012832

Realty Hub

$2,000

1325 Mainsail Dr 1213, NAPLES

2 Beds 2 Baths 843 SqFt Rental MLS® # 225082981

Re/Max Alliance Group

$2,000

2058 Arbour Walk Cir 322, NAPLES

2 Beds 2 Baths 918 SqFt Rental MLS® # 226020300

Century 21 AllPoints Realty

$2,000

↓ $300

760 Augusta Blvd D204, NAPLES

3 Beds 2 Baths 1,294 SqFt Rental MLS® # 226011730

Supreme Rental Solutions PM

$2,000

468 12th Ave S 468, NAPLES

2 Beds 1 Bath 848 SqFt Rental MLS® # 226030459

Daane Properties LLC

$2,000

2730 Cypress Trace Cir 2836a, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226003443

REMAX Affinity Mercato

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$2,400

154 Cypress Way E 1102, NAPLES

$2,395

5 High Point Cir W 104, NAPLES

$2,350

150 Round Key Cir G-15, NAPLES

$2,350

135 Cypress Way E C, NAPLES

$2,300

3298 Megan Ln 2, NAPLES

$2,300

4187 Lakewood Blvd E13, NAPLES

$2,300

1120 Sarah Jean Cir B205, NAPLES

$2,300

1190 Reserve Way 304, NAPLES

$2,300

2860 Citrus Lake Dr R-202, NAPLES

$2,300

7360 Glenmoor Ln 4301, NAPLES

$2,300

1700 Windy Pines Dr 1701, NAPLES

$2,300

112 Bob O Link Way B, NAPLES

$2,300

37 High Point Cir E 305, NAPLES

$2,295

3370 10th St N 1304, NAPLES

$2,250

15171 Cedarwood Ln 3604, NAPLES

$2,250

106 Siena Way 1508, NAPLES

$2,225

5928 Cranbrook Way D202, NAPLES

$2,200

1086 Forest Lakes Dr 303, NAPLES

$2,200

3323 Olympic Dr 716, NAPLES

$2,200

2865 Cypress Trace Cir 203, NAPLES

$2,195

8680 Cedar Hammock Cir 116, NAPLES

$2,175

9521 Avellino Way 2415, NAPLES

$2,150

1315 Mainsail Dr 1115, NAPLES

$2,100

1950 W Crown Pointe Blvd B106, NAPLES

$2,050

1645 Spoonbill Ln C, NAPLES

$2,000

1325 Mainsail Dr 1213, NAPLES

$2,000

2058 Arbour Walk Cir 322, NAPLES

$2,000

760 Augusta Blvd D204, NAPLES

$2,000

468 12th Ave S 468, NAPLES

$2,000

2730 Cypress Trace Cir 2836a, NAPLES