What is downtown Naples like for vacation visitors?

Downtown Naples — centered on Olde Naples and 5th Avenue South and 3rd Street South — offers award-winning dining, art galleries, boutique shopping, and proximity to the beach in a compact, pedestrian-friendly setting. For visitors who want to experience Naples as a place rather than just a beach destination, downtown is the ideal base.

How close are downtown Naples vacation rentals to the beach?

Olde Naples sits directly adjacent to the Gulf Coast — the beach is accessible from virtually any downtown rental in under ten minutes on foot. The Naples Pier at 12th Avenue South is the neighborhood's iconic beach landmark, and the stretch of beach nearby is among Naples' most beautiful.

What types of vacation rentals are available in downtown Naples?

Downtown Naples vacation rentals range from luxury condominiums within walking distance of 5th Avenue South to private estate homes in Olde Naples and the Moorings. Many Olde Naples estates offer private pools and spacious outdoor living. Condominiums along Gulf Shore Blvd offer Gulf views and direct beach access.

What is the price range for downtown Naples vacation rentals?

Condominiums near 5th Avenue South range from $6,000 to $15,000 per month during peak season. Estate homes in Olde Naples range from approximately $15,000 to $50,000 per month. Off-season rates are typically 30-50% lower than peak season pricing.

What are the best restaurants on 5th Avenue South in Naples?

Fifth Avenue South standouts include Campiello for Mediterranean cuisine, Barbatella for American bistro cooking, The English Room for continental fine dining, and Bayside Seafood Grill and Bar for waterfront dining. Third Street South adds Ridgway Bar & Grill, Osteria Tulia, and numerous others.

How do I find and book a downtown Naples vacation rental?

Browse listings above or contact Alpizar & Company at (239) 438-1102. Share your preferred downtown location, group size, dates, and budget — we will identify matching properties. Complimentary assistance with no pressure. Our real estate team also specializes in Olde Naples ownership if your stay inspires that conversation.

Downtown Naples Vacations | Walk to 5th Avenue South & the Beach

$24,000

↑ $4,000

993 8th St S 2, NAPLES

4 Beds 5 Baths 2,473 SqFt Rental MLS® # 225082175

Naples Vacation Properties

$24,000

201 8th St S 208, NAPLES

2 Beds 3 Baths 1,704 SqFt Rental MLS® # 226019627

John R Wood Properties

$23,600

605 6th Ave N, NAPLES

3 Beds 3 Baths 2,300 SqFt Rental MLS® # 226005283

Luxury Real Estate LLC

$22,500

365 5th Ave S 306, NAPLES

2 Beds 2 Baths 1,360 SqFt Rental MLS® # 226026014

Premier Sotheby's Int'l Realty

$22,000

572 11th Ave S 2, NAPLES

3 Beds 4 Baths 2,520 SqFt Rental MLS® # 226009571

John R Wood Properties

New New

$22,000

1165 4th St S 2, NAPLES

3 Beds 4 Baths 2,100 SqFt Rental MLS® # 226031005

Royal Shell Real Estate, Inc.

$22,000

N/A, NAPLES

4 Beds 6 Baths 3,745 SqFt Rental MLS® # 226029856

John R Wood Properties

$21,500

1080 5th St S 1080, NAPLES

3 Beds 3 Baths 2,310 SqFt Rental MLS® # 225069820

Royal Shell Real Estate, Inc.

$20,000

↓ $2,000

991 8th St S 1, NAPLES

4 Beds 4 Baths 2,800 SqFt Rental MLS® # 225073085

Naples Vacation Properties

$20,000

739 7th Ave N, NAPLES

3 Beds 3 Baths 2,253 SqFt Rental MLS® # 226019054

William Raveis Real Estate

$20,000

740 5th Ave N, NAPLES

3 Beds 3 Baths 2,051 SqFt Rental MLS® # 225079434

Naples Trust Real Estate Servi

$20,000

↓ $5,000

600 5th Ave S A-212, NAPLES

3 Beds 2 Baths 2,700 SqFt Rental MLS® # 225074205

Premier Sotheby's Int'l Realty

$18,500

732 7th Ave N, NAPLES

3 Beds 2 Baths 1,829 SqFt Rental MLS® # 226024403

Premier Property Management

$18,000

850 Central Ave 305, NAPLES

2 Beds 2 Baths 1,577 SqFt Rental MLS® # 225075922

Coldwell Banker Realty

$18,000

428 9th St S, NAPLES

3 Beds 4 Baths 4,101 SqFt Rental MLS® # 225080623

Coldwell Banker Realty

$18,000

↑ $2,000

325 3rd St S 6, NAPLES

3 Beds 3 Baths 1,995 SqFt Rental MLS® # 225078435

Gulf Coast International Lux R

$18,000

411 6th St S 202, NAPLES

3 Beds 3 Baths 2,293 SqFt Rental MLS® # 226019320

Premier Sotheby's Int'l Realty

$18,000

433 2nd St S B-202, NAPLES

3 Beds 3 Baths 1,667 SqFt Rental MLS® # 226006846

Coldwell Banker Realty

$18,000

223 11th Ave S, NAPLES

4 Beds 4 Baths 2,691 SqFt Rental MLS® # 226030118

John R Wood Properties

$17,000

850 Central Ave 310, NAPLES

3 Beds 3 Baths 1,663 SqFt Rental MLS® # 225078260

Coldwell Banker Realty

$17,000

995 9th Ave S 6, NAPLES

3 Beds 4 Baths 1,838 SqFt Rental MLS® # 2026029174

Gordon Pass Realty LLC

$16,000

361 1st Ave N, NAPLES

3 Beds 3 Baths 1,500 SqFt Rental MLS® # 225084714

Royal Shell Real Estate, Inc.

$16,000

1155 6th St S, NAPLES

3 Beds 2 Baths 1,384 SqFt Rental MLS® # 226019623

John R Wood Properties

$16,000

900 5th Ave S 303, NAPLES

3 Beds 3 Baths 1,905 SqFt Rental MLS® # 226001313

William Raveis Real Estate

$15,750

↓ $6,750

101 8th St S 302, NAPLES

2 Beds 1 Bath 865 SqFt Rental MLS® # 226007634

John R Wood Properties

$15,750

↓ $6,750

101 8th St S 202, NAPLES

2 Beds 1 Bath 865 SqFt Rental MLS® # 226007611

John R Wood Properties

$15,500

1280 Gordon Dr C, NAPLES

2 Beds 3 Baths 1,920 SqFt Rental MLS® # 226019179

Diversified Real Estate Group

$15,000

1222 Gordon Dr 15, NAPLES

2 Beds 3 Baths 1,200 SqFt Rental MLS® # 226015327

Downing Frye Realty Inc.

$15,000

392 7th Ave S 4, NAPLES

2 Beds 2 Baths 1,600 SqFt Rental MLS® # 226020882

Premier Sotheby's Int'l Realty

$15,000

780 5th Ave S 302, NAPLES

2 Beds 3 Baths 1,449 SqFt Rental MLS® # 226020003

John R Wood Properties

Downtown Naples Vacations

Seasonal Rentals in Olde Naples

$24,000

993 8th St S 2, NAPLES

$24,000

201 8th St S 208, NAPLES

$23,600

605 6th Ave N, NAPLES

$22,500

365 5th Ave S 306, NAPLES

$22,000

572 11th Ave S 2, NAPLES

$22,000

1165 4th St S 2, NAPLES

$22,000

N/A, NAPLES

$21,500

1080 5th St S 1080, NAPLES

$20,000

991 8th St S 1, NAPLES

$20,000

739 7th Ave N, NAPLES

$20,000

740 5th Ave N, NAPLES

$20,000

600 5th Ave S A-212, NAPLES

$18,500

732 7th Ave N, NAPLES

$18,000

850 Central Ave 305, NAPLES

$18,000

428 9th St S, NAPLES

$18,000

325 3rd St S 6, NAPLES

$18,000

411 6th St S 202, NAPLES

$18,000

433 2nd St S B-202, NAPLES

$18,000

223 11th Ave S, NAPLES

$17,000

850 Central Ave 310, NAPLES

$17,000

995 9th Ave S 6, NAPLES

$16,000

361 1st Ave N, NAPLES

$16,000

1155 6th St S, NAPLES

$16,000

900 5th Ave S 303, NAPLES

$15,750

101 8th St S 302, NAPLES

$15,750

101 8th St S 202, NAPLES

$15,500

1280 Gordon Dr C, NAPLES

$15,000

1222 Gordon Dr 15, NAPLES

$15,000

392 7th Ave S 4, NAPLES

$15,000

780 5th Ave S 302, NAPLES