Apartment holiday rentals in Old Naples

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Top-rated apartment rentals in Old Naples

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Guest favourite

Flat in East Naples

5 out of 5 average rating, 7 reviews

Chic resort, 4 pools, walk to 5th Ave Restaurants!

Welcome to Naples finest gated downtown resort, rewarding guests with a measure of privacy and serenity. The resort features an amenity rich environment with marina, waterfront dining and shopping, Euro-style spa, an expansive activity center, three crystal-blue resort pools, multiple hot tubs, meandering lazy river and a complete fitness center. Walk to downtown 5th ave or take the complimentary shuttle to beaches or 5th Ave HAVE A LARGER GROUP? - ASK ABOUT ADDING ANOTHER UNIT TO YOUR BOOKING

Superhost

Flat in Old Naples

5 out of 5 average rating, 4 reviews

Romantic Condo Directly on Downtown 5th Ave

Top floor condominium in highly desirable Downtown Olde Naples! Located in the heart of 5th Ave South. Downstairs you'll find the best of Naples dining, shopping, luxury art galleries, boutiques, ice cream parlors and more! Enjoy a dip in the rooftop pool and spa just steps outside your door. Inside, the kitchen is fully stocked with everything you need to feel at home. Your master bedroom is outfitted with a King size bed. En suite bathroom also has a large walk-in tile shower, and skylight.

Top guest favourite

Flat in Fort Myers Beach

4.98 out of 5 average rating, 115 reviews

Island Oasis Steps From the Sugar Sand Beach

Important Note: This apartment had no damage from hurricanes in 2024. Everything is perfect here. Beaches are beautiful, pool is relaxing and welcoming. Thankfully the island restaurants and bars are also back up and going in fun island style! Beaches are beautiful and our brand new pool is complete and ready to enjoy. Be one of the first to enjoy this complete remodel renovation. No expense was spared here. Top quality memory foam mattresses with high end bed linens for a restful sleep. F

Top guest favourite

Flat in Naples

4.99 out of 5 average rating, 134 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

Superhost

Flat in Naples

4.83 out of 5 average rating, 6 reviews

Lovely Water View Retreat

Enjoy this peaceful and wonderfully located , water view condo near Olde Naples and it’s beautiful beaches. Remodelled and in the very desirable Oyster Bay/Royal Harbor neighborhood Just a mile from the prestigious 5 th Avenue So. shopping and restaurants area as well as boat tours, the Olde Naples historical area including the loved 3rd Street So. area with its lovely Farmer’s Market, and only 2 miles from the beach. A fabulous location for all who would like to enjoy many of Naple’s charms!

Top guest favourite

Flat in Old Naples

5 out of 5 average rating, 14 reviews

Upstairs - 2 Blocks From Everything

This is one of five quaint rental opportunities on a magnificently rebuilt Old Naples Cottage Estate c.1910. Located two blocks from the Gulf of Mexico & Naples Pier and within walking distance of everything 5th Avenue and 3rd Street have to offer. The private entrance to the stairs brings you to a newly renovated, magical spot. Comfortable seating arrangement, full kitchen with marble counters forming a sitting bar, all new equipment, two king bedrooms, and a full bathroom off the kitchen.

Superhost

Flat in Old Naples

4.84 out of 5 average rating, 43 reviews

Beautifully Renovated Condo, Walk to Beach/3rd St

Take a break and unwind at this peaceful oasis. Embrace the laid back lifestyle of the beach when you stay at our downtown Naples condo! The 2-bedroom, 2-bath vacation rental provides updated finishes throughout and wonderful shared amenities. Spend your mornings on the beach, dolphin watching, or perusing the farmers market. Enjoy afternoons on the beach, swimming in the heated on-site pool, or shopping on 3rd St and 5th Ave. You'll love this Old Naples location, promising endless fun!

Top guest favourite

Flat in East Naples

5 out of 5 average rating, 95 reviews

Artistic w Lush Surroundings Quiet Great Location!

For Guests Who Love Privacy! Sunny Studio where Art is highlighted. French Doors to Lg Screened Porch for Outside Dining/Working. Peaceful. Stilt home (8 steps) in Safe, Quiet area w parking right outside. Backyard is yours w BBQ grill, table & chairs. Charmingly Furnished w Recliner, Heavenly King Bed, Convection/Microwave oven, Kitchen Aid stove top & Full Fridge. 83 Mbps at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

Top guest favourite

Flat in Fort Myers Beach

4.98 out of 5 average rating, 118 reviews

Ready to Enjoy again! Everything is brand new!

This vacation rental unit has been totally rebuilt and is now ready to welcome guests again! Nearly everything is brand new and it is likely one of the nicest studio apartments now available on the entire island. Skip the dated condos and hotels and get ready to enjoy this newer, nicer option, located just 1 short block (800 feet) from the sand. As you’ll see from the reviews it had a great track record before the storm, and it’s been rebuilt even better! Enjoy NEW!

Superhost

Flat in Naples Park

4.79 out of 5 average rating, 131 reviews

563 Park Place | Bougain"Villa" | Mins to Beaches

Welcome to 559 Park Place | BougainVilla! Tropical colors make life feel like a permanent vacation in this beautifully decorated, modern Villa. The BougainVilla is freshly updated & fully equipped with all of the comforts of home. Located in the heart of the Vanderbilt Beach area, just minutes to the beaches & the Mercato Shopping & Dining District. This space is designed for our guests & their families to have everything they may need while on vacation.

Top guest favourite

Flat in Park Shore

5 out of 5 average rating, 30 reviews

Park Shore Resort-BLDGC#218*Amazingly remodeled*

*REMODELED 2024* One of the Nicest & most luxurious condos at PSR-Top Floor condo. This condo has been lovingly restored. Park Shore Resort has all the amenities you could want with an on-site restaurant, Heated Pool, BBQ's, Tennis, Pickleball courts, Basketball, Exercise room. In the middle of Naples walking distance to numerous Restaurants & Shops within minutes to the Village Shops on Venetian Bay, Mercato, Waterside Shops, and of course Naples Famous Beaches.

Guest favourite

Flat in Naples Park

4.85 out of 5 average rating, 149 reviews

#Blocks2Beach Lower 1BR1BA LARGE Palm Villa #RITZ

Casual chic décor are features of this fantastic 1 bedroom/1 bath Villa. Quiet spaces and enough room for extended stays or a weekend getaway. Comfortably sleeps 4 guest with sleeper sofa in living room and master bedroom with cozy king bed. Located in the highly sought after Naples Park neighborhood. Close to Naples beautiful white sandy beaches, upscale shopping, fine & casual dining and entertainment to suite any style!