Olde Naples Homes with Cabana Amenities

Welcome to Olde Naples, a picturesque gem nestled along the stunning Gulf Coast of Florida. Renowned for its charming tree-lined streets and historic architecture, Olde Naples exudes a unique blend of coastal elegance and small-town warmth. This vibrant neighborhood is a true reflection of the quintessential Florida lifestyle, where residents enjoy the perfect balance of relaxation and sophistication.

As you stroll through Olde Naples, you’ll discover an array of upscale boutiques, art galleries, and gourmet restaurants that cater to every palate. The pristine beaches, just a stone’s throw away, offer breathtaking sunsets and endless opportunities for outdoor activities, from sunbathing to paddleboarding. The vibrant community spirit is palpable, with events and festivals that bring neighbors together and celebrate the area’s rich culture.

For those seeking a home in this idyllic locale, Olde Naples boasts an impressive selection of properties, many featuring cabana amenities that elevate the living experience. Imagine relaxing by your private cabana, sipping on a refreshing drink while enjoying the gentle coastal breeze. These luxurious outdoor spaces are perfect for entertaining guests or unwinding after a long day.

Whether you’re searching for a charming historic home or a modern retreat, Olde Naples offers a variety of options to suit your lifestyle. Embrace the serene coastal living and vibrant community spirit that makes Olde Naples a sought-after destination for homebuyers. Your dream home awaits in this enchanting neighborhood, where every day feels like a vacation.

Newest Olde Naples Homes with Cabana Amenities

$4,750,000

5 Beds ⋅ 5.5 Baths ⋅ 226025231 MLS

Exceptional Olde Naples living in the heart of it all. Ideally located just 5 blocks from Historic Fifth Avenue South, 8 blocks from Third Street South, and minutes to the City Dock, lovely park overlooking the bay across the street, 888 10th Avenue South offers a sophisticated blend of luxury, comfort, and effortless coastal living. The spacious residence features four bedrooms in the main house plus a private guest cabana above the garage, providing an ideal setting for family and guests. Soaring 11-foot ceilings, Legno Bastone flooring, UMI quartz countertops, and a Thermador Professional Series kitchen showcase the home's elevated finishes. Generously sized primary suites and laundry facilities on both levels add exceptional functionality. The outdoor living spaces are designed for quintessential Naples entertaining, with a fully equipped outdoor kitchen, grilling area, gas fireplace, retractable screens, and sun deck surrounding the beautiful pool and raised spa. Three additional balconies offer glimpses of Naples Bay and the surrounding area. A rare opportunity to enjoy the privacy and comfort of a refined Olde Naples residence within easy walking distance of the very best of downtown Naples.

888 10th AVE S, Naples

$2,700,000

3 Beds ⋅ 3.5 Baths ⋅ 226028473 MLS ⋅ Victor Del Rey BLDG.

A rare opportunity to own a completely renovated residence in the heart of Old Naples, just one mile from the Gulf's white sand beaches and moments from renowned shopping, dining, art galleries and entertainment. This beautifully reimagined three-bedroom, 3.5-bath condominium offers nearly 3,000 square feet of thoughtfully designed living space and includes the rare convenience of a private pool cabana, private one-car garage and an additional assigned covered parking space. Newly renovated and remodeled, the residence blends timeless design with exceptional craftsmanship. Natural light fills the open great room, where wide-plank flooring, detailed custom millwork, designer lighting and volume ceilings give the space a polished, airy feel. The living area extends outdoors to a generous private balcony with views of the community pool and lush tropical landscaping. The gourmet kitchen was designed for everyday living and entertaining, featuring floor-to-ceiling custom cabinetry with soft-close doors and drawers, Italian porcelain countertops and a backsplash with waterfall edges, an oversized island, integrated refrigerator, wine storage and a striking black ILVE range with a matching statement hood. The redesigned laundry room offers additional cabinetry, counter space and storage for added functionality. The spacious primary suite opens directly to the balcony and features dual custom walk-in closets and a beautifully renovated bath with dual vanities, a freestanding soaking tub, an oversized walk-in shower and thoughtfully selected designer finishes. Each guest bedroom offers its en-suite bath, providing comfort and privacy for family and guests. One of the property's distinctive features is the private air-conditioned pool cabana complete with a half bath, offering exceptional flexibility as a home office, fitness room, lounge or additional entertaining space. Additional improvements include updated electrical and thoughtfully planned lighting throughout, 2025 and 2026 appliances, a 2024 HVAC system, a 2026 water heater, secure semi-private elevator access, a gated garage entry and extra storage. Victor Del Rey is an intimate boutique building of only 12 residences, where owners enjoy a heated community pool, grilling area and a navigable Old Naples lifestyle just moments from Fifth Avenue South, Third Street South, the beach and everything downtown Naples has to offer.

705 10th ST S Unit 202, Naples

$499,000

1 Beds ⋅ 1 Baths ⋅ 226025950 MLS ⋅ Castleton Gardens BLDG.

Welcome to Castleton Gardens 204, a rare second floor renovated and beautifully furnished one-bedroom condominium in the heart of Old Naples. This unit features a king-sized bedroom, updated bath, open kitchen with large island and a comfortable living space. Ideally just three blocks to 5th Avenue South, two blocks to Cambier Park and one block to Tin City, with Naples beaches less than a mile away. Ideal for owners and investors, the community allows rentals up to 12 times per year with a 30-day minimum. Amenities include a heated pool, spa and barbecue area set within a charming banyan tree-lined courtyard. Exterior stair access with no elevator! Castleton Gardens 204 presents a rare opportunity to own a turnkey property that captures the essence of Naples living while delivering exceptional versatility.

980 7th AVE S Unit 204, Naples

$380,000

1 Baths ⋅ 226019629 MLS ⋅ Cove Inn BLDG.

Discover the perfect mix of laid-back coastal charm and savvy investing at this beautifully upgraded efficiency unit at the iconic Cove Inn on Naples Bay. Wake up to breathtaking, picture-perfect water views from your private patio, where a thoughtful privacy wall frames the shimmering marina and Naples Bay, your own personal slice of paradise. This fully furnished, turnkey efficiency features a kitchenette and stylish upgrades throughout, making it as comfortable as it is effortless to own. Guests and owners alike will revel in resort-style amenities, including a sparkling pool and beloved Chickee Bar, all set against the backdrop of one of Naples' most storied waterfront destinations. Cove Inn stands apart as one of the rare waterfront hotels in historic Old Naples, perfectly positioned at the gateway to Crayton Cove, a charming village of eclectic boutiques and restaurants hugging the banks of City Dock and Naples Bay. Stroll to world-class shopping and dining along famous 5th Avenue South, or take a short walk to the sugar-white sands of Naples Beach. Whether you're seeking a personal retreat, a high-demand rental income property, or both, this condo hotel unit delivers an exceptional opportunity in one of Southwest Florida's most coveted destinations.

900 Broad AVE S Unit 117, Naples

$464,000

1 Beds ⋅ 1 Baths ⋅ 226017941 MLS ⋅ Castleton Gardens BLDG.

RARE OPPORTUNITY IN OLDE NAPLES – TURNKEY & FULLY REMODELED! Experience the ultimate Naples lifestyle in this stunning, 1st-floor residence at the gated Castleton Gardens. Perfectly situated just blocks from the world-class dining of 5th Avenue South, the shops of 3rd Street South, and the pristine white sands of Naples Beach. No expense was spared in this top-to-bottom renovation. The chef-inspired kitchen features sleek quartz countertops, a custom island, an efficient induction cooktop, and premium Bosch appliances. The open-concept living area flows seamlessly onto elegant flooring, while the master suite offers a spacious walk-in closet with custom built-ins. Additional premium upgrades include impact windows and doors for peace of mind and an in-unit washer/dryer for total convenience. Castleton Gardens provides a serene, private oasis with a lushly landscaped courtyard, heated community pool, and spa. Sold turnkey furnished, this property is a "just bring your toothbrush" retreat or a high-demand seasonal rental. Whether you're looking for a chic second home or a savvy investment, this gem in the heart of 34102 won’t last.

980 7th AVE S Unit 109, Naples

$349,000

1 Beds ⋅ 1 Baths ⋅ 226000135 MLS ⋅ Castleton Gardens BLDG.

Welcome to an exquisite property nestled in the vibrant city of Naples, offering an unparalleled blend of luxury and convenience. This gated community features exceptional amenities, including a community pool and spa, providing a serene oasis for relaxation. The residence boasts stunning views of Downtown Naples and an inviting outdoor space featuring a grilling area, perfect for entertaining. The interior is thoughtfully renovated with upscale touches such as quartz countertops, an undermounted sink, and sleek new ceramic flooring. The kitchen is equipped with premium stainless steel appliances, complemented by modern cabinets and enhanced by designer lighting and fans. The bathroom showcases a seamless glass shower door, adding to the sense of elegance, while hurricane windows throughout ensure safety and peace of mind. Ample storage is achieved with expertly installed closet organizers. Ideally located, this home offers proximity to the vibrant Naples beaches, pier, lively nightlife, refined restaurants, bustling art district, and the local theater, promising a lifestyle of sophistication and excitement.

980 7th AVE S Unit 101, Naples

$2,980,000

2 Beds ⋅ 2 Baths ⋅ 224018674 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches.This expansive 2-bedroom, 2-bathroom residence defines elevated living. Unit 303 features a thoughtfully designed open layout, a private one-car garage, and a generous balcony that overlooks the oversized rooftop pool, offering stunning views of downtown Naples. The Cayden offers more than just beautifully crafted homes—it elevates everyday living with exceptional amenities, including a dog run, fitness center, community room, and a secure mailroom. For those seeking a truly personalized touch, this property presents a rare opportunity to work directly with builders to customize the interior features and reflect your unique style.

180 9th ST S Unit 303, Naples

$3,590,000

2 Beds ⋅ 2 Baths ⋅ 224018668 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches. This exceptional 2-bedroom, 2-bathroom residence embodies refined and comfortable upscale living at its best. Unit 302 offers a well-thought-out open layout, a private one-car garage, and a spacious balcony that provides sweeping views of the oversized rooftop pool and downtown Naples. The Cayden delivers more than just beautiful homes—it enhances your lifestyle with premium amenities, including a dog run, fitness center, community room, and secure mailroom. For those looking to add a personal touch, this property offers a unique opportunity to collaborate directly with builders to customize the interior features to your taste.

180 9th ST S Unit 302, Naples

$3,200,000

2 Beds ⋅ 2 Baths ⋅ 224018654 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches. Step into refined coastal living with this inviting 2-bedroom, 2-bathroom residence. Unit 202 features a smart, open layout with a private one-car garage and a spacious balcony that overlooks the expansive rooftop pool, offering sweeping views of downtown Naples. The Cayden is more than just a collection of homes—it's a lifestyle, with exclusive amenities such as a dog run, a state-of-the-art fitness center, a community room, and a secure mailroom. Plus, future homeowners will enjoy the unique opportunity to collaborate with builders to personalize their interiors, creating a space that truly reflects their style.

180 9th ST S Unit 202, Naples

$2,950,000

2 Beds ⋅ 2 Baths ⋅ 224018659 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches. This elegant 2-bedroom, 2-bathroom residence perfectly captures the charm of upscale coastal living. Unit 203 features a thoughtfully designed open layout, complete with a private one-car garage and a spacious balcony that overlooks the expansive rooftop pool, offering stunning views of downtown Naples. Beyond the stunning residences, The Cayden delivers a premium lifestyle with top-tier amenities, including a dog run, state-of-the-art fitness center, community room, and secure mailroom. Future residents will also have the unique opportunity to collaborate with builders to personalize their interiors, tailoring every detail to reflect their own style.

180 9th ST S Unit 203, Naples

$3,890,000

3 Beds ⋅ 2.5 Baths ⋅ 224018642 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches. Discover the pinnacle of coastal luxury in this expansive 3-bedroom plus den, 2.5-bathroom residence. Unit 301 is designed to embody the essence of modern elegance, featuring an open-concept layout, a private two-car garage, and a spacious balcony that offers one of the most spectacular views in the area. Imagine waking up to sweeping vistas of lush palm trees framed by a vast, endless sky—truly a breathtaking sight that elevates every moment. The Cayden takes coastal living to new heights, offering premium amenities such as a dog run, state-of-the-art fitness center, community room, and secure mailroom. For those who want to make this home uniquely theirs, the property provides an exceptional opportunity to collaborate with builders and customize interior finishes, creating a space that reflects your personal style.

180 9TH ST S Unit 301, Naples

$3,950,000

3 Beds ⋅ 2.5 Baths ⋅ 224018643 MLS ⋅ The Cayden Olde Naples BLDG.

NOW SELLING! Introducing The Cayden Olde Naples – an exclusive retreat nestled in the heart of Naples, Florida to be completed May 2026! With just six residences, this boutique community offers unparalleled privacy and a prime location, only 0.2 miles from the lively 5th Avenue and a short mile to Naples’ pristine beaches. This spacious 3-bedroom + den, 2.5-bathroom unit perfectly captures the essence of sophisticated coastal living. Unit 201 showcases an open, thoughtful layout with a private two-car garage, a generous balcony overlooking an oversized rooftop pool, and stunning views of downtown Naples. The Cayden’s design goes beyond individual residences, offering exceptional amenities like a dog run, fitness center, community room and secured mail room. The property provides an exceptional opportunity for future residents to collaborate directly with builders, tailoring interior features to reflect personal style.

180 9TH ST S Unit 201, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.