Apartment holiday rentals in Old Naples

4.98 out of 5 average rating, 43 reviews

Upstairs - 2 Blocks From Everything

This is one of five quaint rental opportunities on a magnificently restored 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.

5.0 out of 5 average rating, 4 reviews

Modern & Chic 5th Ave Historic Naples

Highly desirable & exclusive condo directly on 5th Ave S in Olde Naples. Experience the night life and luxury Naples has to offer right just a few steps away. We're only 5 blocks from Naples famous white sand beaches. 5th Ave offers some of Naples most prestigious and high-end dining and shopping. From cafes, bistros, boutiques, ice cream parlors, designer jewelers, fine art, 5th Ave's modern and historic district has it all. Your condo is completely outfitted for a luxury and stress-free vacati

4.99 out of 5 average rating, 146 reviews

A sunset view features a wooden pier stretching over waves, with silhouettes of people gathering at the end. Warm hues of orange and yellow illuminate the sky, creating a serene backdrop against the gently rolling ocean.

Flat in Naples

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

A well-lit bedroom features a spacious bed adorned with decorative pillows and a soft blanket. Two windows with light-filtering shades provide natural light. A minor desk is placed beside a comfortable chair, complemented by stylish blue accent pieces against neutral walls.

4.95 out of 5 average rating, 105 reviews

Coastal Retreat - 5th Ave & Beaches 10 min away

Welcome to your perfect Naples Coastal Retreat! Step into this beautifully decorated, brand-new apartment designed for comfort and relaxation in the highly desired Bayshore Arts District. Located just minutes from the beautiful Naples beach and 5th Ave. Whether you're here for a weekend getaway or an extended stay, you'll love the thoughtful touches, stylish decor, and unbeatable location. Walkable restaurants, live music, waterfront drinks, and nearby trails. We are pet-friendly! :)

A bright bedroom features a spacious bed with a soft yellow coverlet. A small dining table with two chairs is positioned nearby. A painting adorns the wall, with light entering through the window. A laundry area is visible, providing added convenience.

4.99 out of 5 average rating, 109 reviews

Rare Gem, Fast WiFi, 3 Min to Town, King Bed

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. FAST WiFi at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

4.96 out of 5 average rating, 249 reviews

A serene beach scene captures the sun setting on the horizon, casting warm golden reflections on the calm water. Fine white sand fills the foreground, enhancing the peaceful ambiance of the location.

Flat in Naples

Naples Getaway for Two • Central to Everything

This apartment offers the perfect combination of convenience, comfort, and value. Located in the heart of naples. It is only 3 miles from the beach, 3 miles from the downtown district and less than a mile from shopping centers with Publix, Target and more. Guest favorites: ✔ 1 comfortable queen mattress ✔ Fully equipped kitchen ✔ Fast Wi-Fi ✔ Strong A/C ✔ Easy parking ✔ Self check-in ✔ Minutes to beaches ✔ Close to restaurants & shopping ✔ Great for weekend getaways or longer stays

4.9 out of 5 average rating, 21 reviews

Modern 5th Ave Beach Condo!

Where Fifth Avenue Meets the Gulf! Located just two blocks from the beach, ON 5th Avenue South & 1 block from 3rd Street South. Walk to world-class restaurants, shops, art galleries and more. Or just simply relax and unwind at home in this newly renovated, never-lived-in 2BR/2BA end unit with outdoor space to enjoy the coastal breeze. The heated pool & modern coastal finishes complete this perfect retreat. Unbeatable location. Parking included. Available weekly, monthly, or annually.

4.86 out of 5 average rating, 124 reviews

A large community pool is framed by a spacious patio area, with lounge chairs neatly arranged around it. A clubhouse with a distinctive roof is visible in the background, surrounded by palm trees and lush landscaping. The sky is partly cloudy, contributing to a bright atmosphere.

Flat in North Naples

Oasis Naples Condo 2BR/2Bath

Soak up the warm southwest Florida sun and enjoy a clean modern home with gorgeous views. This newly renovated condo is a short 5 minute car ride to Naples Beaches and 15 minutes to downtown. Two bedroom, two full bath home is the perfect quiet place for a couple’s retreat or for working remotely with high speed internet. The main pool IS open dawn to dusk!!! It’s a two minute walk within the community! (The smaller pool by the condo is closed and still waiting for completion.)

A light-filled living area features a spacious beige sofa and a comfortable lounge chair. A coffee table sits in front, with decorative items placed on it. A dining table for four is visible, accompanied by abstract wall art and soft lighting from ceiling fans.

4.96 out of 5 average rating, 138 reviews

Cozy 1 Bedroom Villa - Beautiful Naples, Florida!

Perfect One Bedroom Villa only 2.5 miles from the beach and 2 miles from beautiful 5th Ave in Naples! This Villa is perfect for those coming to Naples on Vacation, for work, or seasonally! It has everything you need to live comfortably for a short or long period of time including a 200 sq foot private front porch. Enjoy everything Naples has to offer within a short drive! This unit is perfect for 1-2 guests. It can fit up to 3 with a pullout couch in the living room.

4.71 out of 5 average rating, 14 reviews

Waterfront Condo near Tin City |Balcony + views|

Stay right on Naples Bay — minutes from Tin City, 5th Ave South, and boat docks. This bright space features a loft-style layout with a spiral staircase, a modern open design, and a private screened balcony perfect for enjoying the Florida breeze. Guests can unwind by the resort-style pool or explore nearby dining, shopping, and beaches. Ideal for couples, families, or small groups looking for both comfort and location.

4.97 out of 5 average rating, 134 reviews

A modern kitchen is equipped with sleek white cabinetry and stainless steel appliances. A large island with two brown bar stools offers a space for dining or casual gatherings. Soft lighting and large windows contribute to a bright and open atmosphere.

Flat in North Naples

Las Casitas in Naples #2

Welcome to your home away from home! Beautifully renovated condo, located close to shops, restaurant, and the beach. This condo is located at the edge of a natural preserve; giving you the best of both worlds: you can sit in the backyard and enjoy a quiet and relaxing afternoon, or take a short walk and find yourself at local restaurants, the beach, wine bars, or shops.

A light-filled seating area features a white sofa adorned with a decorative pillow, complemented by two patterned armchairs. A circular ottoman sits at the center, surrounded by a natural fiber area rug. Lush greenery can be seen through shuttered windows, enhancing the serene atmosphere.

4.96 out of 5 average rating, 28 reviews

Olde Naples 2BR - Near beach and 5th Ave

Welcome to Maison Du Soleil, a quiet 2 bedroom, 1 bath condo in the heart of downtown Naples. It's close to all that Naples has to offer: beaches, shopping, restaurants, golf, East Naples pickleball. The second-floor condo is light-filled and well-appointed. It comes fully stocked with everything you need to enjoy your stay, whether it's for a week or for the season.

Popular amenities for Old Naples apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.84 out of 5 average rating, 19 reviews

A bright bedroom is furnished with a spacious bed dressed in crisp white linens. Two bedside lamps provide gentle illumination. A ceiling fan rotates above, and large windows invite natural light, while sheer curtains frame a view of greenery outside.

Flat in Naples

Near Downtown & Beaches & Pool

A large swimming pool is surrounded by lush palm trees and vibrant tropical landscaping. Comfortable lounge chairs are arranged around the pool, with umbrellas offering shade. A rock formation features a waterfall, enhancing the serene atmosphere of the resort's outdoor space.

5.0 out of 5 average rating, 17 reviews

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

5.0 out of 5 average rating, 22 reviews

Flat in Park Shore

Lux Lakefront Resort | Beach 3 MIN Drive | 70"TVs

A welcoming entrance is framed by lush greenery and palm trees. A paved pathway leads to the building's entrance, which is highlighted by elegant white architecture and soft sunlight casting gentle shadows. The atmosphere is serene, showcasing the condo's accessibility and appealing curb appeal.

5.0 out of 5 average rating, 10 reviews

Best Beach, Dining & Shopping! 1.5 Blocks-beach!

4.92 out of 5 average rating, 49 reviews

Luxury Condo 2BR at Resort near 5th Ave & Beach

4.6 out of 5 average rating, 5 reviews

2/2 White Sands Naples - 2brm 2 bath

5.0 out of 5 average rating, 58 reviews

Flat in Vanderbilt Beach

Seashell Beach, your place to relax and enjoy.

A bright bedroom features a spacious bed with a turquoise blanket and subtle accent pillows. Natural light enters through two large windows. A small nightstand with a lamp is positioned next to the bed, while a modern kitchenette and bathroom entrance are visible in the background.

4.93 out of 5 average rating, 83 reviews

Coastal Guest Suite Near Downtown

Private apartment rentals

5.0 out of 5 average rating, 10 reviews

Flat in Park Shore

Newly Remodeled, Naples Escape 2 Kings, Pickleball

4.84 out of 5 average rating, 61 reviews

15 Beautiful near beach w Free Heated Pool and Spa

A bright studio features a queen-sized bed with a turquoise coverlet and decorative pillows. Natural light floods the room, highlighting the light wood flooring and modern furnishings. A small dining area is visible, with artwork showcasing a coastal theme.

4.99 out of 5 average rating, 67 reviews

Naples Gem|Perfect for 2|Beach 10Min|BBQ|Parking

A screened-in balcony features comfortable seating arranged around a coffee table. A view of the horizon can be seen, showcasing the gradient of colors at sunset. Ceiling fans are installed to provide airflow and enhance relaxation.

5.0 out of 5 average rating, 49 reviews

The Fitz

A spacious living area features a large sectional sofa in a warm brown tone, paired with a coffee table on a textured area rug. A ceiling fan provides airflow, while natural light filters through the window adorned with blinds. A flat-screen TV is mounted on the wall.

4.96 out of 5 average rating, 26 reviews

Brand new unit! 2 miles to Beach

4.93 out of 5 average rating, 14 reviews

Flat in Park Shore

Beautiful Updates - Relaxing Views - Close to Pool

4.94 out of 5 average rating, 17 reviews

The Tropic

A spacious living area is highlighted by a comfortable blue sectional sofa, paired with a light coffee table. A dining table can be seen in the background, complemented by an open kitchen. Natural light fills the room, accentuating the soft color palette.

4.83 out of 5 average rating, 76 reviews

541 Seashell Cottage | Pool-Spa

Apartment rentals with a hot tub

4.99 out of 5 average rating, 107 reviews

A screened-in pool area features a spacious swimming pool with a built-in seating area and spa. Lounge chairs are positioned beside the pool, and a covered patio area is visible above, offering shaded seating options. Lush greenery surrounds the space, enhancing the serene atmosphere.

Flat in Fort Myers Beach

Seaside oasis studio with with heated pool

5.0 out of 5 average rating, 34 reviews

Greenlinks Flamingo Golf Villa at Lely Resort

5.0 out of 5 average rating, 13 reviews

Lely Resort Condo · Pool · Near Beach · Sleeps 6

A comfortably arranged living space includes a light-colored sofa and a blue accent chair, positioned around a wooden coffee table. Shelving displays books and decor pieces. Natural light enters through large windows covered by blinds, complemented by colorful artwork on the walls.

4.89 out of 5 average rating, 18 reviews

Adorable cottage, pool/hot tub, 1.5 mile to beach

A serene lanai features red seating on either side of a decorative black table, set against a backdrop of lush greenery visible through large glass screens. A stylized rug lies beneath the furniture, contributing to the inviting space for relaxation.

4.96 out of 5 average rating, 26 reviews

The Coral in Lely Resort 2 Kings-Heated Pool to 89

An open living area features contemporary furnishings, including a light-colored sofa and a dark coffee table. A spacious island with seating is seen in the background, complementing an adjacent fully-equipped kitchen. Warm lighting fixtures hang above, enhancing the inviting atmosphere.

5.0 out of 5 average rating, 4 reviews

The Oasis: Naples Luxury Condo and Dock

4.73 out of 5 average rating, 26 reviews

Flat in Fort Myers Beach

Sand Dollar South - Beachfront

A modern living area is shown, featuring a cozy sofa, a glass dining table, and large sliding doors that open to a scenic outdoor view. Natural light fills the space, highlighting decorative wall art and a stylish ceiling fan.