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NOT AVAILABLE FOR JANUARY 2027, FEBRUARY 2027, MARCH 2027, AND APRIL 2027. Experience the Tranquil Beauty of Resort-Style Living in Naples, Florida Welcome to 2920 Cypress Trace Circle #204, a beautifully furnished 2-bedroom, 2-bath vacation rental nestled in the highly sought-after community of Cypress Woods Golf & Country Club in North Naples. This meticulously maintained second-floor condo offers a perfect blend of comfort, style, and convenience for those seeking a seasonal escape in paradise. Step inside to an open-concept layout flooded with natural light, featuring tile flooring in the main living areas, plush carpeting in the bedrooms, and elegant furnishings throughout. The spacious living room seamlessly extends to a private screened lanai with serene lake and golf course views—an ideal setting for morning coffee or relaxing sunsets. The kitchen is fully equipped and designed for both casual dining and entertaining, with granite countertops, stainless steel appliances, ample cabinetry, and a convenient breakfast bar. The primary suite boasts a king-size bed, walk-in closet, and an en-suite bath with dual vanities and a walk-in shower. The guest bedroom is thoughtfully appointed with twin beds and easy access to a full second bathroom. As a guest of Cypress Woods, you’ll enjoy full access to an impressive array of amenities including an 18-hole championship golf course, pro shop, resort-style pool and spa, tennis and pickleball courts, a well-equipped fitness center, on-site dining at the clubhouse, and miles of walking and biking trails surrounded by lush landscaping and wildlife. Conveniently located just minutes from the best of Naples—fine dining, world-class shopping, pristine Gulf beaches, and cultural attractions—this property offers an exceptional seasonal retreat for those who crave both relaxation and recreation.
#226020273

NAPLES

2920 Cypress Trace CIR 204

2 Beds

2 Baths

1,625 Sq.Ft.

$5,500

MLS#: 226020273

NOT AVAILABLE FOR FEBRUARY, MARCH, AND APRIL 2027. Welcome to this beautifully appointed vacation residence located at 2730 Cypress Trace Circle, Naples, FL 34119, where comfort, elegance, and relaxed Florida living come together seamlessly. Nestled within a desirable and well-maintained Naples community, this inviting home offers a tranquil retreat surrounded by lush landscaping and a serene atmosphere. Designed with both style and functionality in mind, the residence features a bright, open-concept layout that enhances natural light and creates an effortless flow between living, dining, and entertaining spaces. The living area is warm and welcoming, ideal for relaxing after a day exploring Naples’ world-class beaches, dining, and shopping. A thoughtfully designed kitchen provides ample cabinetry, generous counter space, and a layout that makes both everyday meals and casual entertaining a pleasure. Whether preparing a quick breakfast before heading out or hosting guests in the evening, the space is both practical and inviting. The bedrooms offer a peaceful escape, with comfortable proportions and a calming ambiance designed for restful nights. Bathrooms are well-appointed and maintained with a clean, timeless aesthetic. Every detail of the home has been curated to support a relaxed and enjoyable stay. Step outside and enjoy the Florida lifestyle at its finest. Whether sipping morning coffee or unwinding in the evening breeze, the outdoor surroundings provide a quiet setting perfect for relaxation. Conveniently located in Naples, this property places you just a short drive from pristine Gulf beaches, championship golf courses, shopping destinations, and a vibrant dining scene. Ideal as a seasonal getaway or extended vacation retreat, this residence delivers comfort, convenience, and the quintessential Southwest Florida lifestyle.
#226013488

NAPLES

2730 Cypress Trace CIR 2812

2 Beds

2 Baths

1,232 Sq.Ft.

$5,500

MLS#: 226013488

Welcome to St. Maarten at Pelican Bay, a premier high-rise residence offering the quintessential Naples lifestyle. This beautifully appointed annual rental presents a rare opportunity to enjoy the elegance and amenities of one of Southwest Florida’s most sought-after communities. Situated on Pelican Bay Boulevard, this residence features 2 spacious bedrooms and 2 full bathrooms. The interior showcases tasteful finishes including tile and carpet flooring, custom mirrors, walk-in closets, and turnkey furnishings for effortless living. A well-equipped kitchen with modern appliances—dishwasher, microwave, range, and disposal—complements the open layout, while expansive windows invite natural light and frame serene views of the surrounding landscape. The St. Maarten building offers a wealth of amenities designed for comfort and leisure. Residents enjoy access to a resort-style pool and spa, sauna, fitness center, billiards, library, and social rooms. Just steps away, the Pelican Bay tram provides convenient transportation to the community’s private beach clubs, where you’ll find beachfront dining, cabanas, and water sports. Outdoor enthusiasts will appreciate the walking and biking paths, tennis courts, pickleball, and kayaking facilities, all part of the Pelican Bay lifestyle. Beyond the residence itself, Pelican Bay is renowned for its lush landscaping, vibrant social scene, and unmatched Gulf of Mexico access. Living here means being part of a community that blends tranquility with sophistication, offering both relaxation and recreation at your doorstep.
#225079655

NAPLES

6101 Pelican Bay BLVD 805

2 Beds

2 Baths

1,452 Sq.Ft.

$5,500

MLS#: 225079655

AVAILABLE NOW!!! Welcome to this charming annual rental located at 523 103rd Avenue North, Naples, FL 34108, offering comfort, convenience, and the desirable Naples lifestyle. Ideally situated just minutes from pristine Gulf beaches, shopping, dining, and entertainment, this home provides an excellent opportunity for long-term living in a prime location. The interior features a bright and functional layout with a seamless flow between the living, dining, and kitchen areas. Generously sized bedrooms provide comfortable retreats with ample storage, while large windows bring in natural light throughout the home. Enjoy close proximity to Mercato, Waterside Shops, and downtown Naples, along with nearby parks, schools, and everyday conveniences. Perfect for those seeking a well-located and comfortable annual rental in one of Naples’ most sought-after areas.
#226015574

NAPLES

523 103rd AVE N

4 Beds

2 Baths

1,974 Sq.Ft.

$5,200

MLS#: 226015574

NOT AVAILABLE FOR JANUARY 2027, FEBRUARY 2027, AND MARCH 2027. 265 Deerwood Circle #10 is a well-appointed second-floor condominium located in the Glen Eagles community within Lely Resort, Naples, Florida. This end-unit condo offers 2 bedrooms and 2 bathrooms across 1,179 square feet of living space. The unit features a split floor plan for privacy, updated kitchen and bathrooms with quartz countertops, and a screened-in lanai overlooking the lake, landscaping, community pool, and golf course. Residents have access to a newly renovated clubhouse that includes an award-winning restaurant, bundled golf, a resort-style swimming area with a gazebo, lap pool, outdoor hot tub, spa, fitness center, and lighted tennis, pickleball, and bocce courts. The property is steps away from the community pool and hot tub, and the beautifully maintained grounds are ideal for leisurely walks. Please note that pets and smoking are not allowed in this unit.
#226015578

NAPLES

265 Deerwood CIR 10

2 Beds

2 Baths

1,179 Sq.Ft.

$5,000

MLS#: 226015578

One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to this spacious annual rental in the desirable Victoria Park community of North Naples. This 3-bedroom, 2-bath single-family home offers over 2,200 sq. ft. of comfortable living space with a split-bedroom layout, cathedral ceilings, and an open kitchen featuring granite countertops and stainless steel appliances. Step outside to your private outdoor retreat with a screened lanai, pool, and spa—perfect for relaxing, entertaining, and enjoying the Florida lifestyle year-round. Additional highlights include a 2-car garage and a prime Naples location close to shopping, dining, schools, parks, and Gulf beaches. Victoria Park residents also enjoy community amenities including a pool, playground, tennis courts, sidewalks, and lake/boat dock area. Schedule your private showing today and experience North Naples living at its best!
#226022419

NAPLES

1089 Nottingham DR

3 Beds

2 Baths

2,218 Sq.Ft.

$5,000

MLS#: 226022419

NOT AVAILABLE FOR JANUARY 2027, FEBRUARY 2027, AND MARCH 2027. Welcome to this stunning 2-bedroom, 2-bath condo with a detached garage, located at 2820 Cypress Trace Cir #2023 in the prestigious Cypress Woods Golf and Country Club. This beautifully designed second-floor residence offers a harmonious blend of comfort and elegance, ensuring an unforgettable stay. Highlighting your stay will be the newly renovated Club House, renowned for its friendly and welcoming members who create a warm and loving community atmosphere. The Club House also features an award-winning restaurant, adding to the delightful amenities available to residents including bundled golf, a lap pool, swimming pool, spa, fitness center, and lighted tennis courts. Enjoy all the benefits of membership, including discounts at the restaurant and pro shop. As you enter the residence, you are greeted by a spacious hallway that leads to an inviting living area. The well-equipped kitchen, featuring a cozy dining nook and a breakfast bar, is perfect for casual meals and gatherings. The formal dining area flows effortlessly into the living room, which boasts a volume ceiling, creating a bright and airy ambiance. Sliding doors open to a serene lanai, where you can relax and take in the picturesque views of the tranquil lake. The expansive primary bedroom serves as a peaceful retreat, complete with an en-suite bathroom and a generous walk-in closet. The guest bedroom includes a twin Murphy bed setup, making it versatile as a den or office, and it also has its own en-suite bathroom. Conveniently situated just across from the community pool, you can enjoy a refreshing swim at your leisure. Located in North Naples, this condo offers easy access to shopping, dining, and I-75, ensuring you are never far from the best that Southwest Florida has to offer. Discover the ultimate vacation experience at 2820 Cypress Trace Cir #2023, where luxury, convenience, and community come together to create a perfect seasonal retreat.
#226018231

NAPLES

2820 Cypress Trace CIR 2023

2 Beds

2 Baths

1,094 Sq.Ft.

$5,000

MLS#: 226018231

Welcome to your slice of paradise in the heart of Bonita Springs! Located in the desirable Bonita Fairways community, this beautifully maintained vacation rental at 26680 Bonita Fairways Boulevard offers the perfect blend of comfort, convenience, and the relaxed Florida lifestyle. Designed for effortless living, this inviting residence features a bright, open layout filled with natural light, creating a warm and welcoming atmosphere from the moment you step inside. The living and dining areas flow seamlessly, making it ideal for entertaining or simply unwinding after a day of sunshine and coastal adventures. The well-appointed kitchen provides ample cabinetry and workspace, perfect for preparing everything from casual breakfasts to evening meals at home. Bonita Fairways is a gated community known for its friendly atmosphere and outstanding amenities, including a public golf course, clubhouse, community pool, fitness center, and more. Best of all, you’re just minutes from Bonita Springs’ world-famous beaches, Coconut Point Mall, fine dining, entertainment, and easy access to Naples and Fort Myers. Contact: Perry James – Signal Property Management – (239) 571-2530
#226004789

BONITA SPRINGS

26680 Bonita Fairways BLVD 201

2 Beds

2 Baths

1,216 Sq.Ft.

$4,500

MLS#: 226004789

NOT AVAILABLE FOR FEBRUARY 2027 and MARCH 2027. Nestled in the heart of Naples, this beautifully furnished vacation rental at 2925 Cypress Trace Circle #201 offers a serene escape with a touch of luxury. Located in the prestigious gated community of Cypress Woods Golf & Country Club, this 2-bedroom, 2-bathroom condo is the perfect retreat for anyone looking to enjoy the best of Florida living. Upon entering, you’ll be greeted by an open and airy floor plan, with abundant natural light streaming through large windows. The living room is spacious and welcoming, opening onto a private screened lanai with stunning views of the lake and lush greenery—ideal for enjoying your morning coffee or evening cocktails. The master bedroom features an en-suite bathroom, walk-in closet, and more lake views, creating a peaceful sanctuary for relaxation. The guest bedroom is equally inviting, with plenty of space and privacy. This rental is fully equipped with modern conveniences, including a well-appointed kitchen with stainless steel appliances, in-unit laundry, and access to high-speed internet and cable TV. Just steps from your door, you can indulge in a variety of community amenities, including an 18-hole championship golf course, tennis courts, resort-style pools, a fitness center, and on-site dining options at the clubhouse. Whether you’re looking for a quiet getaway or an active vacation filled with golf and recreation, this property offers the perfect balance of comfort and lifestyle. Plus, with Naples’ pristine beaches, upscale shopping, and dining just a short drive away, you’ll have everything you need for an unforgettable stay.
#226019318

NAPLES

2925 Cypress Trace CIR 201

2 Beds

2 Baths

1,094 Sq.Ft.

$4,500

MLS#: 226019318

Build your dream home here. Easy access to SR82, shopping, restaurants, schools, local parks, Hertz arena, Fort Myers Airport.
#220059657

LEHIGH ACRES

509 Eisenhower BLVD

None Beds

None Baths

0.236 acres

$4,000

MLS#: 220059657

Great lot in Lehigh to build your new home. Nice size lot and this is the time to buy land!
#217027042

LEHIGH ACRES

1714 Scott AVE

None Beds

None Baths

0.5001 acres

$4,000

MLS#: 217027042

Live like a millionaire for just $4,000 a month in this meticulously upgraded 1,300 square feet unfurnished two bedroom, two and a half bath Olde Naples townhouse with garage and lanai. When you enter this property it feels like you have stepped on a fine yacht because everything you can imagine is perfect. There is nothing even close to the quality of this property that is available for annual rental in all of Naples at this price. I hope you will give us a call so that we can show you the quality of this property. The unit was completely remodeled two years ago. The location is 1130 5th St. South in Olde Naples. Just a few steps to some of the best restaurants in Naples on 3rd. Street and a short walk to the world famous beaches of Naples, Fla. Contact: Perry James – Signal Property Management – (239) 571-2530
#226012591

NAPLES

1130 5th ST S B

2 Beds

2 Baths

1,300 Sq.Ft.

$4,000

MLS#: 226012591

Great lot to build your dream home. Priced to sell!
#217024578

LEHIGH ACRES

2913 75th W ST

None Beds

None Baths

0.2501 acres

$3,500

MLS#: 217024578

Great lot ready for you to build your dream home. Priced to sell!
#217024762

LEHIGH ACRES

3004 68th W ST

None Beds

None Baths

0.25 acres

$3,500

MLS#: 217024762

Great lot priced to sell!!! Bring an offer and build your dream home asap!
#216038487

LEHIGH ACRES

3226 31st W ST

None Beds

None Baths

0.282 acres

$3,400

MLS#: 216038487

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* Listings identified with the FMLS IDX logo come from FMLS and are held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request. © 2024. First Multiple Listing Service, Inc.
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