Condo holiday rentals in Old Naples

A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.

4.92 out of 5 average rating, 171 reviews

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

FamilyLocationHot tub

4.96 out of 5 average rating, 101 reviews

A serene courtyard features a large pool surrounded by lounge chairs and palm trees. An oversized spa is positioned adjacent to the pool, with lush green foliage framing the scene, offering a sense of tranquility and relaxation in the outdoor space.

Condo in Naples Park

The Sunset @ Naples Boutique | Walk 2 Beaches

Introducing The Sunset @ Naples Boutique! Our most spacious flat @ Naples Boutique; Sunset has 2 bathrooms w step-free entry showers, 2 bedrooms both w King beds. Conveniently situated oceanside of the US41, Vanderbilt beach to the left of us and Delnor Wiggins State Park beach to right. Fabulous shopping, dining & nightlife in Mercato and surrounding area! The courtyard pool and oversized spa will have you sun ledge bathing by day and will illuminate the courtyard for a different ambiance eac

LocationFamilyCheck-in

A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.

4.94 out of 5 average rating, 118 reviews

Lush tropical 1st floor getaway in Naples

Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

ValueLocationWalkability

A spacious pool area is surrounded by lush palm trees and vibrant flowers. The water is calm, with small fountains creating gentle ripples. Loungers line the pool's edge, inviting relaxation under the sun. Sunlight reflects off the surface, enhancing the serene atmosphere.

4.96 out of 5 average rating, 339 reviews

Lely Greenlinks Golf Resort Luxury Condo

This beautiful and spacious 2-bedroom, 2 bath condo is luxurious, impeccably clean, well-stocked - and perfect for your next vacation getaway! Greenlinks Golf Resort is situated within the prestigious Lely Resort Golf & Country Club in Naples. It is just a two minute walk over to the clubhouse where you can tee off on the Lely Flamingo or Mustang golf courses. Ideal central location between downtown Naples and Marco Island, you are just 15 minutes from downtown or beaches in either location.

LocationValueWi-Fi

4.9 out of 5 average rating, 184 reviews

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!

LocationValueGetting around

A bright and airy living area features a comfortable sofa paired with decorative pillows. A glass coffee table rests atop tiled flooring, while a dining table is positioned nearby. A flat-screen TV is mounted on the wall, and wall art adds a coastal touch.

4.93 out of 5 average rating, 99 reviews

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

**Newly renovated, reopened December 2024** Spend your Naples getaway in this completely renovated sun drenched, luxury corner unit. Cross the street to the sunny beaches of the Gulf of Mexico. Stroll to the famous Naples Fishing Pier. Walk a block to 3rd St S for fine dining, casual eateries, boutiques, and more. Relax indoors with 3 flat-screen TV's or by the pool. At the end of your day grab your beach chair an view the spectacular Naples sunsets. It does not get any better than this!

FamilyValueGetting around

A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.

4.92 out of 5 average rating, 140 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.

FamilyLocationOutdoor spaces

The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.

4.98 out of 5 average rating, 128 reviews

Fun At The Beach

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier (rebuilding currently) and 3rd Ave 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 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 refrigerator.

LocationFamilyTV

The outdoor patio features two wooden lounge chairs with decorative cushions positioned around a small wooden table. Lush greenery and trees provide natural shade, while a picnic table is visible in the background, inviting outdoor gatherings.

4.89 out of 5 average rating, 161 reviews

5th Ave & Beaches 10 Minutes Away! 2 BD/2 BA

Bring your family and friends to our Southwest Florida paradise! This stylish space is the newest addition to our profile. Located in Naples Florida and within a 7 min drive to 5th Ave shops, restaurants, and beaches. Enjoy a 10 min walk to Celebration Park and local restaurants. Guests can enjoy this newly remodeled condo that has everything you will need for your Naples getaway. **If you have a larger party, inquire and view our profile about the 3 other condos on this property.

FamilyLocationIndoor spaces

Condo in Vanderbilt Beach

The image captures a striking sunset over the ocean, featuring a gradient of oranges and yellows blending into deep blues. The calm water reflects the warm colors, creating a serene and expansive view of the horizon, with the last light of day disappearing into the distance.

4.96 out of 5 average rating, 144 reviews

Your Beach Hideaway

Welcome to Your Beach Hideaway! A short 3 minute walk to beautiful Vanderbilt Beach in North Naples, Fl. Light and Airy 1 bedroom condo with Wi-Fi only 1000 ft from the sand! Less than a mile to shopping, restaurants, bicycle rentals, fitness center and Paragon Pavilion movie theaters. 1.2 miles to Whole Foods and Mercato also with restaurants, shopping and Silver Spot theater. Everything you need is provided all the way to Beach chairs, umbrella and a blender for Daiquiris!

FamilyValueDecor

4.93 out of 5 average rating, 136 reviews

A modern living area is highlighted by a white sectional sofa and a circular glass dining table surrounded by stylish white chairs. Large windows provide views of a tranquil outdoor space with greenery and water, complementing the bright interior decor.

Condo in Naples

Beautiful Pool 5m to the Beach Downtown & Shopping

**Condo - Naples Modern Retreat** Welcome to Naples Modern Retreat, a fully renovated 2 bedroom, 2 bathroom condo nestled in a Tennis Resort in the heart of Naples, Florida. 6 miles to downtown and the beaches. This property offers a harmonious blend of scenic views including beach, canal, garden, lake, marina, ocean, pool, and resort vistas, ensuring a stay full of breathtaking beauty and modern luxury. ** Popular Amenities ** 2 bicycles, 5 beach chairs and umbrella

FamilyValueHospitality

Condo in Fort Myers Beach

The eight-story building stands prominently along the vibrant green waters of Lovers Key State Park. Lush landscaping surrounds the property, with residential docks and a restaurant visible along the water's edge, enhancing the serene coastal environment.

4.94 out of 5 average rating, 186 reviews

Lovers Key Resort/Ft Myers Beach/Condo/Pool/View

HIGH FLOOR Located on the 8th floor of Lovers Key Resort Unit 803, Fort Myers/Bonita Springs, FL. Private balcony overlooking the stunning water views of Lovers Key State Park and its beautiful environment Dolphins, manatees, exotic birds, and more spotted right from your balcony. Pool / Hot tub / gym

ValueLocationIndoor spaces

Popular amenities for Old Naples condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

An open living area features a comfortable sofa and armchair, complemented by natural light flowing through sliding glass doors. A dining table for four is positioned near the kitchen, and a neutral rug enhances the relaxed ambiance. Picturesque outdoor views are visible beyond the patio.

4.98 out of 5 average rating, 101 reviews

Park Shore Resort-Deluxe Condo 1st FloorBLDGE #134

LocationValueBathroom

5.0 out of 5 average rating, 30 reviews

Naples Luxurious Resort Retreat with Lazy River

ValueFamilyNearby

4.98 out of 5 average rating, 50 reviews

Downtown Naples Beach Condo, Off of Famous 5th Ave

LocationFamilyWalkability

A modern kitchen features white cabinetry and a spacious island with white quartz countertops. Stainless steel appliances, including a microwave and oven, are visible. A television displaying a beach scene adds a touch of relaxation, while natural light fills the open layout.

5.0 out of 5 average rating, 42 reviews

Luxurious condo steps to beach with heated pool!

FamilyLocationNearby

A private, landscaped patio features two swivel chairs positioned around a small table. Lush greenery and flowering plants surround the area, providing a serene view of a lake in the background. The natural setting invites relaxation and enjoyment of the outdoors.

5.0 out of 5 average rating, 91 reviews

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

ValueLocationAmenities

Superhost

4.8 out of 5 average rating, 5 reviews

Naples Pier Condo 123

FamilyLocationBathroom

An aerial view captures the condo complex positioned near the Gulf of Mexico. The scene features the peaceful sea, sandy beach, and palm trees, with a glimpse of the community pool nestled within the property.

5.0 out of 5 average rating, 18 reviews

Old Naples Beach Condo

LocationFamilySleep quality

An aerial view captures the vibrant coastal community, with turquoise waters meeting sandy beaches in the distance. Palm trees and residential properties create a lush landscape. A private parking lot is visible near the foreground, indicating easy access to the beach and surrounding amenities.

4.97 out of 5 average rating, 62 reviews

Luxury condo. 300 steps to beach & Naples Pier.

LocationValueCheckout

Pet-friendly condo rentals

4.92 out of 5 average rating, 172 reviews

A cozy living room is presented with two comfortable couches and a glass coffee table. A large smart TV is mounted on the wall, displaying a scenic beach view. Soft lighting from lamps creates a relaxed atmosphere, while a decorative rug adds texture beneath the seating area.

Condo in Naples Park

Seas the Day! Beach*Wine*Dine*Relax. And repeat!

LocationValueParking

A light-filled living area features a large, comfortable sectional sofa arranged around a white coffee table. Floor-to-ceiling glass doors lead to a balcony, while a stylish television is mounted on the wall. Soft, neutral colors enhance the serene atmosphere.

4.92 out of 5 average rating, 12 reviews

Amazing Old Naples Property!

LocationParkingBeach

A modern outdoor area features a sleek heated pool and jacuzzi, surrounded by landscaped greenery. Glass railings provide unobstructed views of the river. Natural stone surfaces complement the serene environment, creating a peaceful retreat for relaxation.

4.85 out of 5 average rating, 55 reviews

Casa Di Napoli: 2/2 Chic Retreat/Private Pool

FamilyValueOutdoor spaces

Superhost

5.0 out of 5 average rating, 5 reviews

Tranquil Luxury 2BR Condo Near Beach & 5th Ave

FamilyLocationIndoor spaces

A bright living area is showcased, featuring a comfortable sofa and accent chairs. Natural light floods in through large windows dressed with soft curtains. A framed artwork adds color to the wall, while a coffee table sits centrally, complemented by a round mirror reflecting the space.

5.0 out of 5 average rating, 17 reviews

SoCe Flats 304 - West Facing 1+Den Luxury Condo

FamilyLocationCleanliness

A modern kitchen features new stainless steel appliances, including a refrigerator and electric stove. Light-colored cabinetry complements the marble countertop, while a patterned backsplash adds texture. Sink and storage drawers enhance functionality, with dish towels neatly arranged nearby.

4.96 out of 5 average rating, 78 reviews

Newly Remodeled 2 bedroom, 2 miles to the beach!

ValueFamilyHospitality

4.91 out of 5 average rating, 70 reviews

Spacious 2BR Lely Resort Condo w/Lake View | Pool

FamilyValueWalkability

Superhost

4.9 out of 5 average rating, 48 reviews

10% Weekly Off | Naples Escape – Lely Golf, Pool

LocationValueLaundry

Condo rentals with a pool

4.95 out of 5 average rating, 152 reviews

An aerial view captures a sprawling landscape featuring residential areas interspersed with waterways. The horizon showcases the ocean, with buildings lining both sides of the main road. Lush greenery surrounds the area, providing a sense of tranquility and connectivity to nature.

Condo in Bonita Springs

Amazing Condo-1 mile from Bonita Beach

LocationFamilyCleanliness

Condo in Fort Myers Beach

4.84 out of 5 average rating, 126 reviews

206C Gulf Water Views + 2 bikes + beach gear

LocationValueLaundry

A spacious lanai features two vibrant green chairs and a small table, overlooking a tranquil body of water. Lush greenery and a wooden bridge are visible, creating a serene view that enhances the outdoor living experience.

4.9 out of 5 average rating, 119 reviews

Park Shore Resort258 Top Loc. View, Pool, Tennis +

FamilyValueAir conditioning

5.0 out of 5 average rating, 26 reviews

A clear pool is surrounded by sun loungers under blue umbrellas. The white building features arched balconies adorned with potted flowers. Additionally, an outdoor dining area with shaded seating is visible beside the pool, creating a relaxing environment.

Condo in Naples

New Naples condo. Minutes to beach & shopping.

FamilyLocationWalkability

5.0 out of 5 average rating, 58 reviews

Golf Condo @ Lely | Free Rounds | Pool + Spa

FamilyValueLong stay

An outdoor balcony features a round dining table surrounded by several chairs, offering stunning views of the ocean and a glowing sunset. The serene atmosphere is enhanced by soft colors in the sky, while a small table stands beside a chair.

5.0 out of 5 average rating, 23 reviews

The Club at Naples Cay 1101

LocationValueCheck-in

The outdoor balcony features a dining table surrounded by four patterned chairs. A lounge area is present with a spacious seating arrangement. The view beyond includes lush greenery and distant ocean glimpses, with a high-rise building visible in the background.

4.94 out of 5 average rating, 63 reviews

Westshore Naples Cay #202- Stunning Ocean view

FamilyValueWalkability

An outdoor dining area is showcased on a spacious lanai, featuring a round table surrounded by four cushioned chairs. A stunning view of the ocean and vibrant sunset colors are visible through expansive glass railings, enhancing the tranquil atmosphere.