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

$5,500

↓ $700

4525 Fluvia Ave, NAPLES

2 Beds 1 Bath 1,050 SqFt Rental MLS® # 226015625

John R Wood Properties

$5,500

1222 Gordon Dr 2, NAPLES

2 Beds 2 Baths 1,125 SqFt Rental MLS® # 226022848

Compass Florida LLC

$5,500

2611 Citrus Lake Dr C-203, NAPLES

3 Beds 2 Baths 1,710 SqFt Rental MLS® # 226006127

Downing Frye Realty Inc.

$5,500

↑ $1,300

5045 Cedar Springs Dr 203, NAPLES

2 Beds 2 Baths 1,427 SqFt Rental MLS® # 225082984

Parkline Realty

$5,500

760 Wiggins Lake Dr 205, NAPLES

2 Beds 2 Baths 1,179 SqFt Rental MLS® # 226007412

WeichertRealtors-ParadiseHomes

$5,500

↓ $1,000

1902 Princess Ct, NAPLES

4 Beds 3 Baths 2,174 SqFt Rental MLS® # 226016894

Coldwell Banker Realty

$5,500

↑ $600

333 Harbour Dr 211, NAPLES

2 Beds 2 Baths 975 SqFt Rental MLS® # 225074540

Naples Flat Fee Realty LLC

$5,500

1290 Yesica Ann Cir G-105, NAPLES

2 Beds 2 Baths 1,168 SqFt Rental MLS® # 226010803

Premier Sotheby's Int'l Realty

$5,500

4147 Los Altos Ct, NAPLES

2 Beds 2 Baths 1,540 SqFt Rental MLS® # 226026856

Coastal Intl Properties LLC

$5,500

9566 Trevi Ct 4944, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226025813

Bluewater Signature Realty LLC

$5,500

2880 Cypress Trace Cir 103, NAPLES

2 Beds 2 Baths 1,372 SqFt Rental MLS® # 226017167

SunStream Realty

$5,500

9735 Acqua Ct 611, NAPLES

2 Beds 2 Baths 1,408 SqFt Rental MLS® # 226029676

Naples Breeze Realty

$5,500

1802 Kings Lake Blvd 2-101, NAPLES

2 Beds 2 Baths 1,465 SqFt Rental MLS® # 226010523

Premier Sotheby's Int'l Realty

$5,500

13140 Hamilton Harbour Dr F4, NAPLES

2 Beds 2 Baths 1,340 SqFt Rental MLS® # 226017085

Royal Shell Real Estate, Inc.

$5,500

↑ $500

630 95th Ave N S, NAPLES

3 Beds 2 Baths 1,411 SqFt Rental MLS® # 226003432

REMAX Affinity Mercato

$5,500

840 Gulf Pavillion Dr 103, NAPLES

2 Beds 2 Baths 1,179 SqFt Rental MLS® # 225073993

Premier Sotheby's Int'l Realty

$5,500

2790 Cypress Trace Cir 2228, NAPLES

2 Beds 2 Baths 1,661 SqFt Rental MLS® # 225085056

William Raveis Real Estate

$5,500

1025 Tarpon Cove Dr 203, NAPLES

2 Beds 2 Baths 1,225 SqFt Rental MLS® # 225072135

Premier Sotheby's Int'l Realty

$5,500

↓ $500

671 100th Ave N, NAPLES

3 Beds 2 Baths 1,164 SqFt Rental MLS® # 224055793

Easy Living Property Services

$5,500

410 Bayfront Pl 2301, NAPLES

3 Beds 2 Baths 1,633 SqFt Rental MLS® # 226018199

Compass Florida LLC

$5,500

↓ $500

8066 Tauren Ct, NAPLES

3 Beds 2 Baths 1,821 SqFt Rental MLS® # 226018777

Coldwell Banker Realty

New New

$5,500

2730 Cypress Trace Cir 2820, NAPLES

2 Beds 2 Baths 1,373 SqFt Rental MLS® # 226027557

SunStream Realty

$5,500

↑ $500

4126 Belair Ln C4, NAPLES

2 Beds 2 Baths 1,195 SqFt Rental MLS® # 226013399

Century 21 AllPoints Realty

New New

$5,500

5 Bluebill Ave 303-1, NAPLES

2 Beds 2 Baths 1,068 SqFt Rental MLS® # 226030982

Berkshire Hathaway FL Realty

$5,500

1285 Sweetwater Cv 2106, NAPLES

2 Beds 2 Baths 1,378 SqFt Rental MLS® # 226029868

Coldwell Banker Realty

$5,500

↓ $1,000

9596 Trevi Ct 5435, NAPLES

2 Beds 2 Baths 1,194 SqFt Rental MLS® # 226028991

Parkline Realty

$5,500

↓ $500

9234 Veneto Pl, NAPLES

3 Beds 3 Baths 2,032 SqFt Rental MLS® # 226021450

Downing Frye Realty Inc.

$5,500

↓ $250

4402 Novato Ct, NAPLES

3 Beds 2 Baths 1,983 SqFt Rental MLS® # 226026582

John R Wood Properties

$5,500

2711 Citrus Lake Dr F305, NAPLES

3 Beds 2 Baths 1,480 SqFt Rental MLS® # 225085223

Downing Frye Realty Inc.

$5,500

6555 Valen Way G201, NAPLES

3 Beds 2 Baths 1,450 SqFt Rental MLS® # 226016905

Alfred Robbins Realty Group

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$5,500

4525 Fluvia Ave, NAPLES

$5,500

1222 Gordon Dr 2, NAPLES

$5,500

2611 Citrus Lake Dr C-203, NAPLES

$5,500

5045 Cedar Springs Dr 203, NAPLES

$5,500

760 Wiggins Lake Dr 205, NAPLES

$5,500

1902 Princess Ct, NAPLES

$5,500

333 Harbour Dr 211, NAPLES

$5,500

1290 Yesica Ann Cir G-105, NAPLES

$5,500

4147 Los Altos Ct, NAPLES

$5,500

9566 Trevi Ct 4944, NAPLES

$5,500

2880 Cypress Trace Cir 103, NAPLES

$5,500

9735 Acqua Ct 611, NAPLES

$5,500

1802 Kings Lake Blvd 2-101, NAPLES

$5,500

13140 Hamilton Harbour Dr F4, NAPLES

$5,500

630 95th Ave N S, NAPLES

$5,500

840 Gulf Pavillion Dr 103, NAPLES

$5,500

2790 Cypress Trace Cir 2228, NAPLES

$5,500

1025 Tarpon Cove Dr 203, NAPLES

$5,500

671 100th Ave N, NAPLES

$5,500

410 Bayfront Pl 2301, NAPLES

$5,500

8066 Tauren Ct, NAPLES

$5,500

2730 Cypress Trace Cir 2820, NAPLES

$5,500

4126 Belair Ln C4, NAPLES

$5,500

5 Bluebill Ave 303-1, NAPLES

$5,500

1285 Sweetwater Cv 2106, NAPLES

$5,500

9596 Trevi Ct 5435, NAPLES

$5,500

9234 Veneto Pl, NAPLES

$5,500

4402 Novato Ct, NAPLES

$5,500

2711 Citrus Lake Dr F305, NAPLES

$5,500

6555 Valen Way G201, NAPLES