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

$45,000

↓ $5,000

210 Central Ave, NAPLES

5 Beds 6 Baths 4,600 SqFt Rental MLS® # 226022755

John R Wood Properties

$45,000

678 11th Ave S, NAPLES

4 Beds 4 Baths 3,394 SqFt Rental MLS® # 226000790

Royal Shell Real Estate, Inc.

$45,000

↑ $3,000

783 11th Ave S, NAPLES

4 Beds 5 Baths 3,582 SqFt Rental MLS® # 226004166

Gulf Coast International Lux R

$45,000

195 2nd Ave N, NAPLES

5 Beds 6 Baths 4,434 SqFt Rental MLS® # 225075483

John R Wood Properties

$44,000

↑ $1,100

47 8th Ave S, NAPLES

2 Beds 2 Baths 2,500 SqFt Rental MLS® # 225082838

William Raveis Real Estate

$43,500

255 2nd Ave N, NAPLES

6 Beds 7 Baths 4,351 SqFt Rental MLS® # 225083529

William Raveis Real Estate

$42,750

↑ $10,750

354 1st Ave N, NAPLES

4 Beds 5 Baths 3,100 SqFt Rental MLS® # 225075485

John R Wood Properties

$42,500

431 1st Ave N, NAPLES

4 Beds 4 Baths 3,702 SqFt Rental MLS® # 225075488

John R Wood Properties

$42,000

206 1st Ave N, NAPLES

4 Beds 3 Baths 2,216 SqFt Rental MLS® # 225075499

John R Wood Properties

$35,000

↑ $13,000

370 6th Ave S, NAPLES

4 Beds 3 Baths 2,488 SqFt Rental MLS® # 225080735

Naples Trust Real Estate Servi

$35,000

↑ $5,000

476 1st Ave N, NAPLES

4 Beds 4 Baths 2,700 SqFt Rental MLS® # 226001787

Royal Shell Real Estate, Inc.

$35,000

433 5th St S, NAPLES

3 Beds 4 Baths 3,220 SqFt Rental MLS® # 225084507

Gulf Coast International Lux R

$30,000

↑ $10,000

877 7th St S, NAPLES

3 Beds 3 Baths 1,900 SqFt Rental MLS® # 225072191

Naples Homes and Rentals Inc

$30,000

1375 Gordon Dr, NAPLES

4 Beds 3 Baths 2,150 SqFt Rental MLS® # 226007225

Premier Sotheby's Int'l Realty

$30,000

295 6th St N, NAPLES

3 Beds 3 Baths 1,868 SqFt Rental MLS® # 226014899

William Raveis Real Estate

New New

$30,000

860 7th St S, NAPLES

3 Beds 2 Baths 2,358 SqFt Rental MLS® # 226030194

Premier Sotheby's Int'l Realty

$30,000

359 2nd Ave N, NAPLES

3 Beds 3 Baths 2,252 SqFt Rental MLS® # 225080202

Royal Shell Real Estate, Inc.

$30,000

201 8th St S 310, NAPLES

2 Beds 3 Baths 1,700 SqFt Rental MLS® # 226018539

Naples Vacation Properties

$30,000

↓ $5,000

444 2nd Ave N, NAPLES

3 Beds 3 Baths 2,776 SqFt Rental MLS® # 226018241

William Raveis Real Estate

$30,000

271 1st Ave S, NAPLES

3 Beds 3 Baths 1,930 SqFt Rental MLS® # 225075501

John R Wood Properties

$28,000

92 10th Ave S, NAPLES

3 Beds 3 Baths 1,790 SqFt Rental MLS® # 226009549

Gulf Coast International Lux R

$26,500

↑ $1,500

Xxxx 11th Ave S, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 226000796

Royal Shell Real Estate, Inc.

$26,500

590 E Lake Dr, NAPLES

4 Beds 3 Baths 2,500 SqFt Rental MLS® # 226005478

Royal Shell Real Estate, Inc.

$26,000

270 5th Ave S H-2, NAPLES

4 Beds 5 Baths 3,576 SqFt Rental MLS® # 226016782

William Raveis Real Estate

$25,000

↑ $1,000

420 Palm Cir E, NAPLES

4 Beds 4 Baths 2,930 SqFt Rental MLS® # 226022366

Compass Florida LLC

$25,000

617 Gulf Shore Blvd N, NAPLES

3 Beds 2 Baths 2,147 SqFt Rental MLS® # 226000328

Coldwell Banker Realty

$25,000

↑ $2,000

295 5th Ave S, NAPLES

2 Beds 2 Baths 1,570 SqFt Rental MLS® # 225073176

Naples Vacation Properties

$25,000

215 3rd Ave N, NAPLES

5 Beds 6 Baths 6,231 SqFt Rental MLS® # 226010516

Halo Home Management LLC

$24,000

150 1st Ave N, NAPLES

3 Beds 2 Baths 2,097 SqFt Rental MLS® # 225069290

John R Wood Properties

$24,000

201 8th St S 209, NAPLES

2 Beds 3 Baths 1,704 SqFt Rental MLS® # 225082885

John R Wood Properties

Downtown Naples Vacations

Seasonal Rentals in Olde Naples

$45,000

210 Central Ave, NAPLES

$45,000

678 11th Ave S, NAPLES

$45,000

783 11th Ave S, NAPLES

$45,000

195 2nd Ave N, NAPLES

$44,000

47 8th Ave S, NAPLES

$43,500

255 2nd Ave N, NAPLES

$42,750

354 1st Ave N, NAPLES

$42,500

431 1st Ave N, NAPLES

$42,000

206 1st Ave N, NAPLES

$35,000

370 6th Ave S, NAPLES

$35,000

476 1st Ave N, NAPLES

$35,000

433 5th St S, NAPLES

$30,000

877 7th St S, NAPLES

$30,000

1375 Gordon Dr, NAPLES

$30,000

295 6th St N, NAPLES

$30,000

860 7th St S, NAPLES

$30,000

359 2nd Ave N, NAPLES

$30,000

201 8th St S 310, NAPLES

$30,000

444 2nd Ave N, NAPLES

$30,000

271 1st Ave S, NAPLES

$28,000

92 10th Ave S, NAPLES

$26,500

Xxxx 11th Ave S, NAPLES

$26,500

590 E Lake Dr, NAPLES

$26,000

270 5th Ave S H-2, NAPLES

$25,000

420 Palm Cir E, NAPLES

$25,000

617 Gulf Shore Blvd N, NAPLES

$25,000

295 5th Ave S, NAPLES

$25,000

215 3rd Ave N, NAPLES

$24,000

150 1st Ave N, NAPLES

$24,000

201 8th St S 209, NAPLES