Holiday rentals in Old Naples

5 out of 5 average rating, 24 reviews

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a 1 BR beach rental condo in the heart of Old Naples, FL, and is perfectly situated a 1/2 block off famous 5th Avenue lined with restaurants and shops and 4 short blocks to the beach. The condo is located in a charming "Old Florida" building surrounded by multi-million dollar estates with a heated pool in the courtyard. The unit is equipped with high speed wifi and has a dedicated work space and desk in the unit. There is a wifi enabled keypad to ensure simple contactless entry!

4.89 out of 5 average rating, 18 reviews

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!

4.98 out of 5 average rating, 109 reviews

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.

5 out of 5 average rating, 85 reviews

Little Gem By the Beach and 5th w/Patio Old Naples

JUST A SHORT WALK TO THE BEACH AND 5th AVE, IN THE HEART OF OLD NAPLES, WITH A RARE, PRIVATE PATIO! Totally renovated in January 2023! A beautiful, one-bedroom, one-bath home, with only a 5-minute stroll to the beach and dining! Just outside the living room is a private, landscaped patio overlooking a pretty lake, which is an unusual and lovely feature of this home! Inside, you'll enjoy a fully-equipped kitchen with granite countertops, a comfortable king bed, and washer/dryer in the condo.

4.92 out of 5 average rating, 118 reviews

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.

4.95 out of 5 average rating, 19 reviews

Downtown Naples Beach Condo, Off of Famous 5th Ave

This peaceful Olde Naples condo is just half a block from dining and shops on famous Downtown 5th Ave and 4 blocks from Naples Beach. This first-floor end-unit condo is perfect for a beach getaway. This clean, modern unit has a pool just feet from the front door, a complete kitchen with updated appliances, a new washer and dryer, comfy furniture, beach chairs and umbrella, and high-speed internet. This property offers a perfect blend of relaxation and convenience to sleep up to 4 guests.

Superhost

5 out of 5 average rating, 3 reviews

Amazing Old Naples Property!

Indulge in this beautifully appointed two-bedroom, two-bath retreat nestled in the heart of Old Naples. Soaring ceilings and an open-concept layout create an airy, welcoming ambiance, complemented by a sleek modern kitchen, in-unit laundry, and a private balcony perfect for al fresco dining or sunset cocktails. Retreat to plush hotel-quality linens and premium mattresses in the primary king suite and secondary full bedroom—each featuring an ensuite bathroom for privacy and convenience.

4.94 out of 5 average rating, 122 reviews

Home in Naples

LUX Oasis~10 min Beach/5th Ave~Custom pool w/shelf

Paradise awaits! This newly updated, 3 bed 3 bath home is just perfect for your family vacation! *10-15 minute drive to our favorite local beaches: Via Miramar and Lowdermilk. *Located on a quiet street just 7 minutes from 5th Avenue!* Our screened in lanai makes our home the perfect mix of indoor/outdoor living! Lay out on our luxury chaise loungers, sip a cocktail, watch the game while taking a dip in the heated pool, grill up some grub, kick back and relax!

Apartment in South Naples

4.95 out of 5 average rating, 153 reviews

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.

5 out of 5 average rating, 7 reviews

Apartment in East Naples

Naples Tyme Retreat

New spring rates! Enjoy Spring at Naples Tyme Retreat — an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, 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.

Superhost

Guest house in Naples

4.81 out of 5 average rating, 148 reviews

Coastal Cabana - 2 Miles to Beach and 5th Ave

The Coastal Cabana is an adorable one-bedroom guest house less than two miles to the beach and the best shopping and dining in Naples. This downtown location in the 34102 zip is unmatched when it comes to beach accessibility and the best of everything downtown Naples has to offer. The Cabana is tucked away in a small, quiet coastal neighborhood walking distance to the Naples Zoo and Conservancy of Southwest Florida, and Gordon River Greenway!

5 out of 5 average rating, 19 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.

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Popular amenities for Old Naples holiday rentals

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Other great holiday rentals in Old Naples

4.91 out of 5 average rating, 53 reviews

Apartment in Naples

3 Bedroom Waterfront Getaway in Downtown Naples!

WilliamRating, 5 stars1 month ago

Nice location near downtown and the Tin City complex. Quiet neighborhood and a great little coffee shop at the Naples Resort a short walk away. The dock in back was a great place for early coffee or a sundown cocktail. Well equipped kitchen and the deck has nice seating and a Bar-B-Que. I would recommend .

4.64 out of 5 average rating, 11 reviews

Olde Naples Paradise 803

NicoleRating, 5 stars1 month ago

We have stayed at this location a few times and love the location. We love to walk and it is a perfect distance from the beach, shops, coffee shops, and restaurants.

4.92 out of 5 average rating, 26 reviews

Sleek Coastal Abode: 1 Block to Naples Beach!

CalvinRating, 5 stars1 month ago

Great location & space.

Home in Old Naples

4.62 out of 5 average rating, 79 reviews

Walk to the Beach and 5th Ave

LeeRating, 5 stars2 months ago

Fantastic location - close to restaurants, galleries, etc. but still private. Joe was very communicative and helpful. Totally satisfied.

5 out of 5 average rating, 6 reviews

Old Naples Condo

PeterRating, 5 stars4 months ago

Very nice place in a great location! Jennifer was great! Just a small fyi. The clear rubber bath matt in the master bath really smells awful. A stong petroleum or bad rubber smell. I would suggest getting another brand. Otherwise everything was great!

5 out of 5 average rating, 8 reviews

LeMalo, Olde Naples Condo, walk to Beach & 5th Ave

Dale & JanRating, 5 stars1 week ago

Perfect location for biking to shops and restaurants or through lovely neighborhoods. Quiet, clean, updated, comfortable, had everything we needed. Table & chairs out front to relax and read, and also had an overhead, which was nice the day it rained. We could open the door and listen to the rain. We’d come back here!

5 out of 5 average rating, 3 reviews

Old Naples Beach Condo

JamesRating, 5 stars2 months ago

Location, location, location! This place is the best, if you're looking for easy walks, as it is situated in the heart of Old Naples, just a 10 minute walk to the Naples Pier and beautiful beaches. One block from great restaurants, and retail shops. The Saturday Farmers Market is a must visit! The condo is perfect for two people, clean, comfortable and easy access on the first floor with no stairs to climb! Enjoyed the use of the large pool during our visit. Only a 15 minute walk away is the infamous Fifth Avenue. Overall a very fun experience and convenient place to stay!