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

$10,000

↑ $1,500

663 110th Ave N, NAPLES

4 Beds 3 Baths 1,936 SqFt Rental MLS® # 2026007122

RE/MAX Realty Group

$10,000

2328 Clipper Way, NAPLES

2 Beds 2 Baths 1,469 SqFt Rental MLS® # 226005520

John R Wood Properties

$10,000

10420 Gulf Shore Dr 121, NAPLES

2 Beds 2 Baths 1,329 SqFt Rental MLS® # 226004993

Alpizar & Company, LLC

$10,000

↑ $4,500

9115 Strada Pl 5211, NAPLES

2 Beds 2 Baths 1,435 SqFt Rental MLS® # 225085055

Berkshire Hathaway FL Realty

$10,000

797 Willowbrook Dr 203, NAPLES

2 Beds 2 Baths 1,701 SqFt Rental MLS® # 225083028

William Raveis Real Estate

$10,000

3951 Gulf Shore Blvd N 1203, NAPLES

2 Beds 2 Baths 1,770 SqFt Rental MLS® # 225083717

William Raveis Real Estate

$10,000

450 Bayfront Pl 4304, NAPLES

2 Beds 2 Baths 1,518 SqFt Rental MLS® # 225081176

Compass Florida LLC

$10,000

↑ $1,000

1747 Sandpiper St B, NAPLES

3 Beds 2 Baths 1,800 SqFt Rental MLS® # 225079753

DC Fiene Realty

$10,000

802 10th Ave S 802, NAPLES

2 Beds 2 Baths 1,480 SqFt Rental MLS® # 225079052

Naples Diamond Realty

$10,000

3400 Gulf Shore Blvd N K2, NAPLES

3 Beds 2 Baths 1,540 SqFt Rental MLS® # 225077642

Compass Florida LLC

$10,000

↑ $1,500

15 Bluebill Ave 406, NAPLES

2 Beds 2 Baths 1,525 SqFt Rental MLS® # 225076534

Sun Realty

$10,000

400 Flagship Dr 1008, NAPLES

3 Beds 2 Baths 1,734 SqFt Rental MLS® # 225076165

Alpizar & Company, LLC

$10,000

7142 Cayo Coco Ln, NAPLES

2 Beds 2 Baths 1,490 SqFt Rental MLS® # 225069863

William Raveis Real Estate

$10,000

8023 Players Cove Dr 6-101, NAPLES

2 Beds 3 Baths 2,091 SqFt Rental MLS® # 225074125

Premier Sotheby's Int'l Realty

$10,000

5501 Heron Point Dr 204, NAPLES

2 Beds 2 Baths 1,230 SqFt Rental MLS® # 225067504

William Raveis Real Estate

$10,000

1060 Borghese Ln 2002, NAPLES

2 Beds 3 Baths 2,349 SqFt Rental MLS® # 225067501

William Raveis Real Estate

$10,000

12885 Brynwood Way, NAPLES

3 Beds 3 Baths 2,489 SqFt Rental MLS® # 225071305

Premier Sotheby's Int'l Realty

$10,000

↓ $5,000

16885 Fairgrove Way 6-201, NAPLES

3 Beds 2 Baths 2,376 SqFt Rental MLS® # 225070472

RMC REALTY INTERNATIONAL

$10,000

8909 Yucatan Ct, NAPLES

2 Beds 2 Baths 1,616 SqFt Rental MLS® # 225068914

Berkshire Hathaway FL Realty

$10,000

250 7th Ave S 301, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 225068977

Coldwell Banker Realty

$10,000

250 7th Ave S 202, NAPLES

2 Beds 2 Baths 1,000 SqFt Rental MLS® # 225068976

Coldwell Banker Realty

$9,995

5815 Persimmon Way, NAPLES

3 Beds 3 Baths 2,900 SqFt Rental MLS® # 225069811

Royal Shell Real Estate, Inc.

$9,900

10307 Gator Bay Ct, NAPLES

2 Beds 2 Baths 1,855 SqFt Rental MLS® # 225078681

Sun Realty

$9,850

↓ $650

538 Avellino Isles Cir 9201, NAPLES

3 Beds 4 Baths 2,717 SqFt Rental MLS® # 225072145

Premier Sotheby's Int'l Realty

$9,800

↑ $2,800

1973 Yellowfin Cir, NAPLES

4 Beds 3 Baths 2,894 SqFt Rental MLS® # 226030205

Premier Sotheby's Int'l Realty

$9,800

2750 Gulf Shore Blvd N 602, NAPLES

2 Beds 2 Baths 1,617 SqFt Rental MLS® # 225077295

Posh International Properties

$9,750

265 Indies Way 1404, NAPLES

3 Beds 3 Baths 2,798 SqFt Rental MLS® # 226017679

Keller Williams Realty Naples

$9,750

550 Forest Hills Blvd, NAPLES

3 Beds 2 Baths 1,650 SqFt Rental MLS® # 225072079

London Foster Realty

$9,650

↓ $100

410 Bayfront Pl 2503, NAPLES

2 Beds 2 Baths 1,511 SqFt Rental MLS® # 225070346

Orlando Regional Realty Inc

New New

$9,500

823 Tanbark Dr 101, NAPLES

3 Beds 2 Baths 1,481 SqFt Rental MLS® # 226031344

Royal Shell Real Estate, Inc.

Naples Vacation Rentals

Naples Vacation Rentals - Active Listings

$10,000

663 110th Ave N, NAPLES

$10,000

2328 Clipper Way, NAPLES

$10,000

10420 Gulf Shore Dr 121, NAPLES

$10,000

9115 Strada Pl 5211, NAPLES

$10,000

797 Willowbrook Dr 203, NAPLES

$10,000

3951 Gulf Shore Blvd N 1203, NAPLES

$10,000

450 Bayfront Pl 4304, NAPLES

$10,000

1747 Sandpiper St B, NAPLES

$10,000

802 10th Ave S 802, NAPLES

$10,000

3400 Gulf Shore Blvd N K2, NAPLES

$10,000

15 Bluebill Ave 406, NAPLES

$10,000

400 Flagship Dr 1008, NAPLES

$10,000

7142 Cayo Coco Ln, NAPLES

$10,000

8023 Players Cove Dr 6-101, NAPLES

$10,000

5501 Heron Point Dr 204, NAPLES

$10,000

1060 Borghese Ln 2002, NAPLES

$10,000

12885 Brynwood Way, NAPLES

$10,000

16885 Fairgrove Way 6-201, NAPLES

$10,000

8909 Yucatan Ct, NAPLES

$10,000

250 7th Ave S 301, NAPLES

$10,000

250 7th Ave S 202, NAPLES

$9,995

5815 Persimmon Way, NAPLES

$9,900

10307 Gator Bay Ct, NAPLES

$9,850

538 Avellino Isles Cir 9201, NAPLES

$9,800

1973 Yellowfin Cir, NAPLES

$9,800

2750 Gulf Shore Blvd N 602, NAPLES

$9,750

265 Indies Way 1404, NAPLES

$9,750

550 Forest Hills Blvd, NAPLES

$9,650

410 Bayfront Pl 2503, NAPLES

$9,500

823 Tanbark Dr 101, NAPLES