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

$15,000

850 Central Ave 203, NAPLES

2 Beds 2 Baths 1,397 SqFt Rental MLS® # 226020175

Naples Vacation Properties

$15,000

1100 8th Ave S 123f, NAPLES

2 Beds 2 Baths 1,440 SqFt Rental MLS® # 226021935

John R Wood Properties

$15,000

544 10th Ave S 202n, NAPLES

3 Beds 2 Baths 1,365 SqFt Rental MLS® # 226026403

John R Wood Properties

$15,000

684 10th Ave S D1, NAPLES

3 Beds 3 Baths 2,321 SqFt Rental MLS® # 225070446

John R Wood Properties

$15,000

↑ $2,000

365 5th Ave S 303, NAPLES

2 Beds 2 Baths 1,090 SqFt Rental MLS® # 226009218

Parkline Realty

$14,175

101 8th St S 304, NAPLES

1 Bed 1 Bath 920 SqFt Rental MLS® # 226008148

John R Wood Properties

$14,175

101 8th St S 210, NAPLES

1 Bed 2 Baths 1,190 SqFt Rental MLS® # 226008147

John R Wood Properties

$14,000

365 5th Ave S 307, NAPLES

2 Beds 2 Baths 1,150 SqFt Rental MLS® # 226023427

Royal Shell Real Estate, Inc.

$14,000

850 Central Ave 202, NAPLES

2 Beds 2 Baths 1,482 SqFt Rental MLS® # 225077436

Coldwell Banker Realty

$14,000

116 3rd St N, NAPLES

3 Beds 3 Baths 1,400 SqFt Rental MLS® # 226023526

Premier Sotheby's Int'l Realty

$13,500

850 Central Ave 311, NAPLES

2 Beds 2 Baths 1,209 SqFt Rental MLS® # 226028209

Gulf Coast International Lux R

$13,500

↓ $750

1222 Gordon Dr 18, NAPLES

2 Beds 3 Baths 1,300 SqFt Rental MLS® # 226022726

Stewart Real Estate Company

$13,500

↑ $3,500

1222 Gordon Dr 14, NAPLES

2 Beds 3 Baths 1,200 SqFt Rental MLS® # 225073581

John R Wood Properties

$13,000

↓ $2,000

375 8th Ave S D, NAPLES

3 Beds 3 Baths 1,915 SqFt Rental MLS® # 226011743

Premier Sotheby's Int'l Realty

$12,600

↓ $5,400

101 8th St S 206, NAPLES

1 Bed 1 Bath 691 SqFt Rental MLS® # 226007620

John R Wood Properties

$12,600

101 8th St S 306, NAPLES

1 Bed 1 Bath 725 SqFt Rental MLS® # 226008180

John R Wood Properties

$12,600

101 8th St S 308, NAPLES

1 Bed 1 Bath 691 SqFt Rental MLS® # 226008184

John R Wood Properties

$12,500

271 Broad Ave S 202, NAPLES

2 Beds 2 Baths 1,500 SqFt Rental MLS® # 225080624

Coldwell Banker Realty

$12,000

↑ $1,000

230 3rd Ave S 4, NAPLES

2 Beds 3 Baths 978 SqFt Rental MLS® # 226018533

Compass Florida LLC

$12,000

↓ $2,500

302 2nd St S 302, NAPLES

2 Beds 2 Baths 1,340 SqFt Rental MLS® # 226012879

Diversified Real Estate Group

$12,000

651 10th Ave S C651, NAPLES

2 Beds 2 Baths 1,241 SqFt Rental MLS® # 226026514

Diversified Real Estate Group

$12,000

430 10th Ave S 305, NAPLES

3 Beds 3 Baths 2,280 SqFt Rental MLS® # 226027583

Douglas Elliman Florida, LLC

$11,025

↓ $4,725

101 8th St S 205, NAPLES

1 Bed 1 Bath 790 SqFt Rental MLS® # 226007639

John R Wood Properties

$11,025

↓ $4,725

101 8th St S 207, NAPLES

1 Bed 1 Bath 691 SqFt Rental MLS® # 226007646

John R Wood Properties

$11,025

101 8th St S 305, NAPLES

1 Bed 1 Bath 790 SqFt Rental MLS® # 226008174

John R Wood Properties

$11,000

271 Broad Ave S 203, NAPLES

2 Beds 2 Baths 1,400 SqFt Rental MLS® # 225080625

Coldwell Banker Realty

$11,000

1080 6th St S, NAPLES

2 Beds 3 Baths 1,584 SqFt Rental MLS® # 226021651

Gulf Coast International Lux R

$11,000

1060 6th St S 1060, NAPLES

2 Beds 3 Baths 1,570 SqFt Rental MLS® # 226023437

Compass Florida LLC

$10,800

↓ $1,000

282 4th St S, NAPLES

2 Beds 2 Baths 1,058 SqFt Rental MLS® # 225084222

ALL IN PROPERTY MANAGEMENT LLC

$10,500

285 5th Ave S 2b, NAPLES

2 Beds 2 Baths 1,568 SqFt Rental MLS® # 226009654

Sun Realty

Downtown Naples Vacations

Seasonal Rentals in Olde Naples

$15,000

850 Central Ave 203, NAPLES

$15,000

1100 8th Ave S 123f, NAPLES

$15,000

544 10th Ave S 202n, NAPLES

$15,000

684 10th Ave S D1, NAPLES

$15,000

365 5th Ave S 303, NAPLES

$14,175

101 8th St S 304, NAPLES

$14,175

101 8th St S 210, NAPLES

$14,000

365 5th Ave S 307, NAPLES

$14,000

850 Central Ave 202, NAPLES

$14,000

116 3rd St N, NAPLES

$13,500

850 Central Ave 311, NAPLES

$13,500

1222 Gordon Dr 18, NAPLES

$13,500

1222 Gordon Dr 14, NAPLES

$13,000

375 8th Ave S D, NAPLES

$12,600

101 8th St S 206, NAPLES

$12,600

101 8th St S 306, NAPLES

$12,600

101 8th St S 308, NAPLES

$12,500

271 Broad Ave S 202, NAPLES

$12,000

230 3rd Ave S 4, NAPLES

$12,000

302 2nd St S 302, NAPLES

$12,000

651 10th Ave S C651, NAPLES

$12,000

430 10th Ave S 305, NAPLES

$11,025

101 8th St S 205, NAPLES

$11,025

101 8th St S 207, NAPLES

$11,025

101 8th St S 305, NAPLES

$11,000

271 Broad Ave S 203, NAPLES

$11,000

1080 6th St S, NAPLES

$11,000

1060 6th St S 1060, NAPLES

$10,800

282 4th St S, NAPLES

$10,500

285 5th Ave S 2b, NAPLES