
Holiday houses in Old Naples
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Top-rated holiday rentals in Old Naples
Guests agree: these stays are highly rated for location, cleanliness and more.

Downtown Marina Retreat
Welcome to our flawlessly remolded condo in Naples, FL, featuring a king and queen bed both with en-suites. With a perfect view of the marina you'll feel like you're in paradise. Located just 2 blocks from 5th Ave and less than a mile from the beach, it's the ideal place for a relaxing getaway. The downstairs suite offers a serene peaceful view and coffee maker and microwave. Our unit includes a wine refrigerator, covered parking, pool/spa washer/dryer, tandem bike, pickleball paddles, and more!

Home Close To Beach & Downtown Naples
We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

Magical Gateway in Naples FL
You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

FUN AT THE BEACH
2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier( to be rebuilt)and 3rd Ave Famous Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king mattress and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refridgerator.

LUXE Oasis | 10 min Beach • HTD Pool+5th Ave •Crib
Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

Downtown Condo at Naples Pier Beach
Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

By the Beach and 5th - Studio Apartment with Pool
Great location! Newly renovated! A studio guest apartment with your own private entrance, full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining & shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention there's also a pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth speaker? This home is 325 square feet of clean cuteness!

Sandy Cove Cottage/Sandy Cove Villa near the beach
Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

Renovated Studio Steps to Naples Beach & Downtown!
Your next Sunshine State retreat begins at this beautiful Naples studio condo! Cross the street to the sunny beaches of the Gulf of Mexico, take a short stroll to the famous Naples Fishing Pier, or walk a block to Third Street South - Naples' destination venue for fine dining, casual eateries, boutiques, and galleries. After a day in the sun, relax in your second-story home-away-from-home featuring a flat-screen cable TV, free WiFi, all new furnishings, and a remodeled kitchen and bathroom.

NEW! ONE BLOCK to the Beach, Restaurants & Shops!
Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

Naples Luxurious Resort Retreat with Lazy River
Naples Tyme Retreat is an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining. Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living. End of year special: Prices reduced for the holiday!

Olde Naples 5th Ave S Penthouse
Enjoy the life of luxury in the heartbeat of Naples in your own high end penthouse overlooking Naples 5th Ave. 5th Ave offers world class fine dining and shopping. Just a few blocks away lies the beautiful white sand beaches of Naples. To the south, you'll find the famous Naples Pier. Relax in the pool or spa right across from your front door, enjoy people watching from your own private balcony. Your rental includes beach chairs, bikes, and more!
Popular amenities for Old Naples holiday rentals
Stay near Old Naples's top sights
Other great holiday rentals in Old Naples

Naples Gem | 10Min Beach | BBQ | Patio | Parking

Studio in artist home close to downtown and beach

Updated, Walk to the Beach and 5th Ave

Olde Naples 2BR - Near beach and 5th Ave

Pool Home Minutes to the Beach

Beach, Sun and Fun! *Beach House * New Listing

Luxury 2-Bedroom. Steps to Naples Beach & Town.

Naples Waterfront Condo-Walk to 5th Ave, beaches
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $517 NZD | $544 NZD | $510 NZD | $515 NZD | $432 NZD | $363 NZD | $366 NZD | $351 NZD | $361 NZD | $427 NZD | $475 NZD | $486 NZD |
| Avg. temp | 18°C | 20°C | 21°C | 24°C | 26°C | 28°C | 29°C | 29°C | 28°C | 26°C | 23°C | 20°C |
Quick stats about holiday rentals in Old Naples

Total holiday rentals
Explore 330 holiday rentals in Old Naples

Nightly prices starting at
Old Naples holiday rentals start at $104 NZD per night before taxes and fees

Verified guest reviews
Over 5,370 verified reviews to help you choose

Family-friendly holiday rentals
220 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
240 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wi-Fi availability
330 of Old Naples holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Old Naples rentals

4.8 Average rating
Old Naples stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Condo rentals Old Naples
- Rentals with beach access Old Naples
- Rentals with pools Old Naples
- Apartment rentals Old Naples
- Fitness-friendly rentals Old Naples
- Waterfront rentals Old Naples
- Rentals with a patio Old Naples
- Serviced apartment rentals Old Naples
- Rentals with a washing machine and dryer Old Naples
- Pet-friendly rentals Old Naples
- Rentals with a hot tub Old Naples
- Beach house rentals Old Naples
- Rentals with a fire pit Old Naples
- Family-friendly rentals Old Naples
- Rentals with an EV charger Old Naples
- Rentals with outdoor seating Old Naples
- House rentals Old Naples
- Rentals with a fireplace Old Naples
- Hotel rooms Old Naples
- Naples Beach
- Captiva Island
- Lovers Key Beach
- Barefoot beach Bonita Springs,FL
- Clam Pass Park
- The Club at The Strand
- Bonita National Golf & Country Club
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Morgan Beach
- Seagate Beach Club
- Cypress Woods Golf & Country Club
- Spanish Wells Country Club
- LaPlaya Golf Club
- The National Golf & Country Club Ave Maria
- Panther Run Golf Club
- The Quarry Golf Club Naples
- Worthington Country Club
- Esplanade Golf & Country Club of Naples
- Del Tura Golf & Country Club
- Park Shore Beach Park
- Sanibel Island Northern Beach
- Gasparilla Island State Park
- Bunche Beach




