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

$9,250

↑ $1,000

7110 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,387 SqFt Rental MLS® # 225070508

John R Wood Properties

$9,000

2048 Holiday Ln, NAPLES

4 Beds 3 Baths 1,600 SqFt Rental MLS® # 226030112

John R Wood Properties

$9,000

3650 Sunset Blvd, NAPLES

3 Beds 4 Baths 1,728 SqFt Rental MLS® # 226029755

Staton Properties, LLC

$9,000

791 94th Ave N, NAPLES

3 Beds 2 Baths 1,400 SqFt Rental MLS® # 226029871

ALL IN PROPERTY MANAGEMENT LLC

$9,000

4001 Gulf Shore Blvd N 303, NAPLES

2 Beds 2 Baths 1,248 SqFt Rental MLS® # 226027498

RE/MAX Hallmark Realty

$9,000

1499 Vintage Ln, NAPLES

3 Beds 2 Baths 1,754 SqFt Rental MLS® # 226028406

Alfred Robbins Realty Group

$9,000

600 L Ambiance Cir 6, NAPLES

3 Beds 2 Baths 1,967 SqFt Rental MLS® # 226027843

Compass Florida LLC

$9,000

410 Bayfront Pl 2502, NAPLES

2 Beds 2 Baths 1,344 SqFt Rental MLS® # 226027419

Compass Florida LLC

$9,000

↓ $1,000

4092 Belair Ln 17, NAPLES

4 Beds 3 Baths 2,000 SqFt Rental MLS® # 226027781

Naples Flat Fee Realty LLC

$9,000

25 Bluebill Ave 1002, NAPLES

3 Beds 2 Baths 1,613 SqFt Rental MLS® # 226027867

Berkshire Hathaway FL Realty

$9,000

458 Countryside Dr, NAPLES

3 Beds 3 Baths 2,127 SqFt Rental MLS® # 226027454

WeichertRealtors-ParadiseHomes

$9,000

765 Willowbrook Dr 1503, NAPLES

2 Beds 2 Baths 1,701 SqFt Rental MLS® # 226026737

Royal Shell Real Estate, Inc.

$9,000

9513 Ironstone Ter 202, NAPLES

4 Beds 3 Baths 2,297 SqFt Rental MLS® # 226026593

Opyt Realty Inc

$9,000

↑ $2,000

1140 5th St S A, NAPLES

3 Beds 3 Baths 1,140 SqFt Rental MLS® # 226025604

Naples Flat Fee Realty LLC

$9,000

8654 Mustang Dr 8, NAPLES

3 Beds 2 Baths 1,466 SqFt Rental MLS® # 226024533

Berkshire Hathaway FL Realty

$9,000

1910 Gulf Shore Blvd N 102, NAPLES

2 Beds 2 Baths 1,376 SqFt Rental MLS® # 226024871

Downing Frye Realty Inc.

$9,000

1200 Gulf Shore Blvd N 404, NAPLES

2 Beds 3 Baths 1,810 SqFt Rental MLS® # 226024156

Berkshire Hathaway FL Realty

$9,000

9204 Quartz Ln 3-101, NAPLES

3 Beds 3 Baths 2,090 SqFt Rental MLS® # 226022059

Opyt Realty Inc

$9,000

3200 Gulf Shore Blvd N 308, NAPLES

3 Beds 2 Baths 1,250 SqFt Rental MLS® # 226021779

Berkshire Hathaway FL Realty

$9,000

9497 Casoria Ct 101, NAPLES

3 Beds 2 Baths 1,883 SqFt Rental MLS® # 226021843

Realty One Group MVP

$9,000

930 Marble Dr, NAPLES

3 Beds 2 Baths 1,850 SqFt Rental MLS® # 226021387

Posh International Properties

$9,000

2400 Gulf Shore Blvd N 603, NAPLES

3 Beds 2 Baths 1,840 SqFt Rental MLS® # 226020923

REMAX Affinity Mercato

$9,000

823 Meadowland Dr 41-2, NAPLES

3 Beds 3 Baths 1,784 SqFt Rental MLS® # 226020018

Royal Shell Real Estate, Inc.

$9,000

929 Marble Dr, NAPLES

3 Beds 2 Baths 1,803 SqFt Rental MLS® # 226020389

Posh International Properties

$9,000

8177 Saratoga Dr 1002, NAPLES

2 Beds 2 Baths 1,880 SqFt Rental MLS® # 226019582

Premier Sotheby's Int'l Realty

$9,000

9550 Ironstone Ter 201, NAPLES

3 Beds 3 Baths 2,297 SqFt Rental MLS® # 226017917

Opyt Realty Inc

$9,000

7052 Live Oak Dr, NAPLES

2 Beds 2 Baths 1,685 SqFt Rental MLS® # 226017428

ALL IN PROPERTY MANAGEMENT LLC

$9,000

8764 Bellano Ct 3-102, NAPLES

2 Beds 2 Baths 1,624 SqFt Rental MLS® # 226014512

Naples Vibe Realty, LLC

$9,000

↑ $5,500

1208 Chelmsford Ct 67, NAPLES

2 Beds 2 Baths 1,556 SqFt Rental MLS® # 226009355

Douglas Elliman Florida, LLC

$9,000

↑ $4,000

15191 Tolmino St, NAPLES

3 Beds 2 Baths 1,950 SqFt Rental MLS® # 225078367

Waterfront Realty Group Inc

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$9,250

7110 Cayo Coco Ln, NAPLES

$9,000

2048 Holiday Ln, NAPLES

$9,000

3650 Sunset Blvd, NAPLES

$9,000

791 94th Ave N, NAPLES

$9,000

4001 Gulf Shore Blvd N 303, NAPLES

$9,000

1499 Vintage Ln, NAPLES

$9,000

600 L Ambiance Cir 6, NAPLES

$9,000

410 Bayfront Pl 2502, NAPLES

$9,000

4092 Belair Ln 17, NAPLES

$9,000

25 Bluebill Ave 1002, NAPLES

$9,000

458 Countryside Dr, NAPLES

$9,000

765 Willowbrook Dr 1503, NAPLES

$9,000

9513 Ironstone Ter 202, NAPLES

$9,000

1140 5th St S A, NAPLES

$9,000

8654 Mustang Dr 8, NAPLES

$9,000

1910 Gulf Shore Blvd N 102, NAPLES

$9,000

1200 Gulf Shore Blvd N 404, NAPLES

$9,000

9204 Quartz Ln 3-101, NAPLES

$9,000

3200 Gulf Shore Blvd N 308, NAPLES

$9,000

9497 Casoria Ct 101, NAPLES

$9,000

930 Marble Dr, NAPLES

$9,000

2400 Gulf Shore Blvd N 603, NAPLES

$9,000

823 Meadowland Dr 41-2, NAPLES

$9,000

929 Marble Dr, NAPLES

$9,000

8177 Saratoga Dr 1002, NAPLES

$9,000

9550 Ironstone Ter 201, NAPLES

$9,000

7052 Live Oak Dr, NAPLES

$9,000

8764 Bellano Ct 3-102, NAPLES

$9,000

1208 Chelmsford Ct 67, NAPLES

$9,000

15191 Tolmino St, NAPLES