Oyster Bay Houses For Rent55+ Active Adult

Oyster Bay contains (25) subdivisions

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Mid-Tier
Ratings
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Results 4 of 4
Oyster Bay, 1400 Jewel Box Ave, Naples, Florida 34102, image 1
Turnkey
$15,000
  • 4 Beds
  • 4 Baths
  • 3,848 SqFt
  • $3.9/SqFt
House for rent in Oyster Bay
1400 Jewel Box Ave, Naples, FL 34102
Experience luxury coastal living at its finest in this stunning 4-bedroom, 4-bath waterfront property, in the heart of naples’ oyster bay. Offering nearly 3, 850 square feet of thoughtfully designed space, this fully furnished rental delivers the perfect blend of comfort, style, and direct water access. Enjoy seamless indoor-outdoor living with corner pocket sliders that open to a resort-style infinity pool, waterfall spa, and a covered outdoor kitchen complete with a gas grill, ideal for entertaining year-round. Upstairs, take in sweeping southern views of naples bay from your private balcony, perfect for sunsets and fireworks. Inside, you’ll find high-end finishes throughout: quartz countertops, stainless steel appliances, tile and hardwood flooring, coffered ceilings, and a tin ceiling over the dining area. Additional perks include a monitored alarm system, three newer hvac units, and a private den with bamboo floors. Ideally located just minutes from downtown naples, white-sand beaches, and world-class shopping and dining, this elevated home remained untouched during recent storms, offering peace of mind and security.
Oyster Bay, 1605 Osprey Ave, Naples, Florida 34102, image 1
Furnished, Negotiable, Turnkey, Unfurnished
$17,500 $4K
  • 3 Beds
  • 2 Baths
  • 1,530 SqFt
  • $11.44/SqFt
House for rent in Oyster Bay
1605 Osprey Ave, Naples, FL 34102
Available weekly, annually, furnished for the season or unfurnished/furnished annually !! Welcome to this royal harbor direct-gulf access waterfront home, ideally situated less than a mile from downtown naples. Enjoy the convenience of walking, biking, or taking your golf cart to the vibrant shopping of 5th avenue south, sunset views from naples pier, or the fine dining and shopping of 3rd street south. This 3-bedroom home, complete with a dedicated office/den, offers impeccable, all new upgrades such as natural oak wood floors, stainless steel kitchen appliances, quartz countertops, and beautifully updated baths. Step outside to discover the home’s true showstopper: 2, 000 sq ft of brick-paved outdoor living space. This lush, tropical retreat is framed by tall palms and vibrant plants, creating a serene setting to relax or entertain around your private, large heated pool. Gather with friends under the custom locally built chickee hut or enjoy a sunset boat cruise from your private dock. Boaters will love the quick, no-bridge access to naples bay and the gulf of mexico. Motivated and ready to help you lease this wonderfully located gorgeous home!
Oyster Bay, 1399 Osprey Ave, Naples, Florida 34102, image 1
Furnished, Negotiable, Turnkey, Unfurnished
$17,500 $500
  • 3 Beds
  • 3 Baths
  • 1,500 SqFt
  • $11.67/SqFt
House for rent in Oyster Bay
1399 Osprey Ave, Naples, FL 34102
This fully renovated coastal waterfront home offers a truly exceptional lifestyle. Framed by elegant christmas & royal palms, a brick-paved driveway, and lush tropical landscaping, it creates a warm, welcoming entrance. Inside, an open floor plan offers stunning water views from every room, along with upscale finishes, including quartz countertops, custom cabinetry, stainless steel appliances, a beverage bar with an ice maker, and elegant all-new porcelain wood-plank styled flooring throughout. Premium details such as crown molding, hurricane-impact doors and windows, and plantation shutters add sophistication and easy flowing opulence. Designed for seamless indoor-outdoor living, this home features a screened-in patio with a spa and a lounge area, perfect for entertaining. The spacious, private backyard is lined with a towering clusia hedge, creating an oasis of privacy. Enjoy the custom wood dock, ideal for watching breathtaking western sunsets or setting out on a night cruise. Located just a short walk from downtown naples and its iconic white sandy beaches, this property combines luxury, privacy, and unmatched waterfront to bay to gulf to beach access. Also available for annual rental!
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Oyster Bay, 1100 Sandpiper St, Naples, Florida 34102, image 1
Unfurnished
$60,000 $15K
  • 5 Beds
  • 5 2/2 Baths
  • 3,600 SqFt
  • $16.67/SqFt
House for rent in Oyster Bay
1100 Sandpiper St, Naples, FL 34102
Brand new 2025 home!Available for season: november, december january, february and march! Bring all offers stoff cooney modern masterpiece: a trophy of timeless elegance located just one mile from naples’ renowned 5th avenue and 1.8 miles from pristine gulf beaches, this architectural marvel boosting sophisticated luxury by star designer tina twigger sets a new standard for luxury living. With nearly 200 feet of direct oyster bay frontage, the property offers an unrivaled waterfront lifestyle, complete with the opportunity to build multiple docks and a nearly 60 ft existing dock, making it a dream for boating enthusiasts. Spanning almost 4, 000 sq. Ft. Of interior space and over 7, 000 sq. Ft. Of total living area, the home features five spacious bedrooms, five full baths, two half baths, and an ergonomic office. At its heart, a 2, 500 sq. Ft. Wrap-around sun terrace seamlessly blends indoor and outdoor living spaces, showcasing breathtaking panoramic water views. Nicknamed the “modern taj mahal, ” this residence stands as a first-of-its-kind masterpiece, celebrated for its exceptional design and meticulous craftsmanship. Boasting over 7, 500 sq. Ft. Of marble finishes—including more than 40 full-size slabs—the home is a testament to timeless elegance. The striking glass-box architecture, with floor-to-ceiling sliders and expansive windows, floods every room with natural light. Built with durability and resilience in mind, the property features concrete duroc walls, water-resistant custom cabinetry, and commercial-grade heavy-duty flood panels, which provide an additional 4 feet of storm protection. This cutting-edge construction has kept the home safe and dry during recent hurricanes, offering unmatched peace of mind. •sustainable living: a high-power solar roof and tesla powerwalls deliver self-sufficient energy, drastically lowering electricity costs while serving as an instant backup generator during outages. •sophisticated ambiance: the residence features a 30+ speaker high-fidelity sound system, three indoor fireplaces, and an oversized outdoor fireplace that beautifully frames the 12x14 hot tub, creating a luxurious and welcoming atmosphere. •the custom light fixtures for the home from multiple famous design houses serve as jewelry throughout outdoor oasis: the meticulously landscaped grounds include three poolside fire bowls, six water features, and over 25 rare exotic palms illuminated by more than 100 warm landscape lights, creating a private tropical retreat. A timeless lifestyle situated in a prime location near naples’ vibrant downtown and stunning beaches, this stoff cooney creation blends convenience, elegance, and innovation. With its seamless integration of indoor and outdoor living, meticulous design, and thoughtful resilience, the home offers more than just a place to live it provides an extraordinary lifestyle.

Subdivision Amenities

Bike Storage
Car Wash Area
Common Laundry
Community Boat Dock
Community Boat Slip
Community Gulf Boat Access
Fish Cleaning Station
Fishing Pier
Guest Room
Internet Access
Pool
See Remarks
Shuffleboard Court
Sidewalk
Storage
Streetlight
Tennis Court(s)
Trash Chute
Underground Utility
Barbecue
Bike Storage
Clubhouse
Common Laundry
Community Boat Dock
None
Pool
Storage

Scores

Walk Score®

Car-Dependent. Most errands require a car.

31

100

Transit Score®

No data.

N/A

Bike Score®

Somewhat Bikeable. Minimal bike infrastructure.

41

100

Sound Score®

Bearable noise.

79

100

Oyster Bay Communities in Naples, FL

Naples
Mid-Tier Homes & Condos

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