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

$3,000

↓ $7,000

260 Southbay Dr 107, NAPLES

1 Bed 1 Bath 592 SqFt Rental MLS® # 226022043

SunStream Realty

$3,000

460 Launch Cir 301, NAPLES

3 Beds 2 Baths 1,630 SqFt Rental MLS® # 226018430

William Raveis Real Estate

$3,000

460 Launch Cir 403, NAPLES

3 Beds 2 Baths 1,475 SqFt Rental MLS® # 226018429

William Raveis Real Estate

$3,000

180 Turtle Lake Ct 210, NAPLES

2 Beds 2 Baths 842 SqFt Rental MLS® # 226027779

Waterfront Realty Group Inc

New New

$3,000

600 Neapolitan Way 223, NAPLES

2 Beds 2 Baths 864 SqFt Rental MLS® # 226031364

My Florida Real Estate, LLC

$3,000

6345 Lexington Court 201, NAPLES

3 Beds 2 Baths 2,100 SqFt Rental MLS® # 226020767

Compass Florida LLC

$3,000

↓ $200

1927 Morning Sun Ln F-27, NAPLES

2 Beds 2 Baths 1,307 SqFt Rental MLS® # 225073894

Kevin Shelly Realty Inc.

$3,000

4210 Looking Glass Ln 4210, NAPLES

2 Beds 2 Baths 1,300 SqFt Rental MLS® # 225079208

Waterfront Realty Group Inc

$3,000

1165 Mainsail Dr 603, NAPLES

2 Beds 2 Baths 843 SqFt Rental MLS® # 226028052

Bluewater Signature Realty LLC

$3,000

9715 Acqua Ct 125, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 225069586

Safe Harbor Real Estate Servic

$3,000

9560 Trevi Ct 4814, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 225071267

Realty One Group MVP

$3,000

1100 8th Ave S 314b, NAPLES

2 Beds 2 Baths 1,040 SqFt Rental MLS® # 226019121

Waterfront Realty Group Inc

$2,995

15 Bluebill Ave 103aa, NAPLES

2 Beds 2 Baths 1,569 SqFt Rental MLS® # 226021304

REMAX Affinity Mercato

$2,995

↓ $205

630 95th Ave N A, NAPLES

3 Beds 2 Baths 1,411 SqFt Rental MLS® # 226003431

REMAX Affinity Mercato

$2,975

3 Bluebill Ave 505, NAPLES

0 Beds 1 Bath 433 SqFt Rental MLS® # 226017852

Realty One Group MVP

$2,975

N/A, NAPLES

3 Beds 2 Baths 1,640 SqFt Rental MLS® # 226019679

Fast Action Realty Inc

$2,950

451 Bayfront Pl 5201, NAPLES

1 Bed 1 Bath 852 SqFt Rental MLS® # 226023325

Downing Frye Realty Inc.

$2,950

↓ $350

7710 Ahoy Ave, NAPLES

3 Beds 2 Baths 1,580 SqFt Rental MLS® # 225081279

Premiere Plus Realty Company

$2,900

↓ $350

1190 Wildwood Lakes Blvd 306, NAPLES

2 Beds 2 Baths 1,042 SqFt Rental MLS® # 225075587

Realty One Group MVP

$2,900

4523 Fluvia Ave, NAPLES

2 Beds 1 Bath 1,050 SqFt Rental MLS® # 225070486

John R Wood Properties

$2,850

↓ $150

1600 Misty Pines Cir 206, NAPLES

2 Beds 2 Baths 1,102 SqFt Rental MLS® # 226026620

Realty One Group MVP

$2,800

9826 Giaveno Cir 1511, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226014827

WeichertRealtors-ParadiseHomes

$2,800

400 Forest Lakes Blvd 106, NAPLES

1 Bed 1 Bath 638 SqFt Rental MLS® # 226027363

Sellstate Prime Realty

$2,800

7753 Haverhill Ct, NAPLES

2 Beds 2 Baths 1,840 SqFt Rental MLS® # 226018157

KW Elevate Luxury

$2,800

↓ $200

291 8th Ave S 291a, NAPLES

1 Bed 1 Bath 550 SqFt Rental MLS® # 226004118

Premiere Plus Realty Company

$2,800

6069 Islandwalk Blvd, NAPLES

3 Beds 3 Baths 1,800 SqFt Rental MLS® # 226018096

Islandwalk Properties, LLC

$2,800

N/A, NAPLES

2 Beds 2 Baths 1,341 SqFt Rental MLS® # 226026985

Fast Action Realty Inc

$2,800

↓ $200

15126 Palmer Lake Cir 101, NAPLES

3 Beds 2 Baths 1,258 SqFt Rental MLS® # 226017911

Coldwell Banker Realty

New New

$2,800

↓ $100

6045 Chardonnay Ln 302, NAPLES

2 Beds 2 Baths 1,414 SqFt Rental MLS® # 226030512

DomainRealty.com LLC

$2,765

4510 Botanical Place Cir 3, NAPLES

3 Beds 2 Baths 1,246 SqFt Rental MLS® # 226027676

Excel Real Estate Services Inc

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$3,000

260 Southbay Dr 107, NAPLES

$3,000

460 Launch Cir 301, NAPLES

$3,000

460 Launch Cir 403, NAPLES

$3,000

180 Turtle Lake Ct 210, NAPLES

$3,000

600 Neapolitan Way 223, NAPLES

$3,000

6345 Lexington Court 201, NAPLES

$3,000

1927 Morning Sun Ln F-27, NAPLES

$3,000

4210 Looking Glass Ln 4210, NAPLES

$3,000

1165 Mainsail Dr 603, NAPLES

$3,000

9715 Acqua Ct 125, NAPLES

$3,000

9560 Trevi Ct 4814, NAPLES

$3,000

1100 8th Ave S 314b, NAPLES

$2,995

15 Bluebill Ave 103aa, NAPLES

$2,995

630 95th Ave N A, NAPLES

$2,975

3 Bluebill Ave 505, NAPLES

$2,975

N/A, NAPLES

$2,950

451 Bayfront Pl 5201, NAPLES

$2,950

7710 Ahoy Ave, NAPLES

$2,900

1190 Wildwood Lakes Blvd 306, NAPLES

$2,900

4523 Fluvia Ave, NAPLES

$2,850

1600 Misty Pines Cir 206, NAPLES

$2,800

9826 Giaveno Cir 1511, NAPLES

$2,800

400 Forest Lakes Blvd 106, NAPLES

$2,800

7753 Haverhill Ct, NAPLES

$2,800

291 8th Ave S 291a, NAPLES

$2,800

6069 Islandwalk Blvd, NAPLES

$2,800

N/A, NAPLES

$2,800

15126 Palmer Lake Cir 101, NAPLES

$2,800

6045 Chardonnay Ln 302, NAPLES

$2,765

4510 Botanical Place Cir 3, NAPLES