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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

New on site 1 day ago
Welcome to Your Serene Escape in Bonita Springs Experience the perfect blend of comfort, elegance, and relaxation in this beautifully maintained vacation rental located in the sought-after community of Seasons at Bonita. Nestled in the heart of Southwest Florida, 28165 Captiva Shell Loop offers a tranquil retreat just minutes away from pristine Gulf beaches, world-class dining, shopping, and countless outdoor adventures. This spacious 3-bedroom, 2-bath single-family home boasts a thoughtfully designed open floor plan, ideal for both quiet getaways and entertaining guests. The light-filled interior features a stylish coastal aesthetic, complete with modern furnishings, luxury vinyl plank flooring, and high ceilings that enhance the sense of space and serenity. At the heart of the home is a gourmet kitchen equipped with stainless steel appliances, granite countertops, a large center island, and ample cabinetry—perfect for preparing everything from beachside snacks to chef-inspired meals. The adjoining dining and living areas flow seamlessly, opening out to a screened lanai where you can enjoy your morning coffee or evening drinks with views of the lush, landscaped backyard. The primary suite is a private sanctuary featuring a king-sized bed, large walk-in closet, and an en-suite bath with dual vanities and a spacious walk-in shower. Two additional guest bedrooms offer cozy accommodations and flexibility for family or visitors. Enjoy access to Seasons at Bonita’s resort-style amenities, including a luxurious pool with lap lanes, pickleball and bocce courts, a fitness center, walking trails, and a social clubhouse — all designed to enhance your vacation lifestyle.
#226020274

BONITA SPRINGS

28165 Captiva Shell LOOP

3 Beds

2 Baths

2,222 Sq.Ft.

$6,950

MLS#: 226020274

New on site 2 days ago
NOT AVAILABLE FOR FEBRUARY 2027 AND MARCH 2027. Discover unparalleled luxury featuring the newly available, exquisite 2023 Wisteria floor plan with a preferred WESTERLY VIEW FOR FANTASTIC SUNSETS. This impressive property spans 3100 sq ft of indoor-outdoor living space, offering 3 beautifully decorated bedrooms, 3 total bathrooms including the master with its en-suite bath, and a private den for secluded work or relaxation, all complemented by a 1-car garage (owner will keep 1 vehicle and leave 1 garage space open for his guest). Professionally decorated by Robb and Stuckey designers, the home comfortably sleeps 8 and boasts numerous upgrades, ensuring unmatched sophistication and convenience. Step outside to an oversized, screened-in lanai with panoramic super-screen for unobstructed views of the serene lake. The outdoor area is an entertainer's dream, featuring a built-in grill and wet bar for alfresco dining and entertaining. Further enhancing the outdoor living experience are the magnificent heated pool and spa, alongside a top-notch outdoor kitchen with upgraded lighting, creating the perfect setting for relaxation and social gatherings. This home's prime location is conveniently close to the clubhouse and the Overlook Bar and Grill, keeping you connected to all Naples has to offer, including the shopping and dining districts of 5th Ave S and 3rd St S, as well as the beautiful Naples Pier, making it an ideal escape to paradise. NO SMOKING AND NO PETS, ensuring a pristine and tranquil living environment for all residents. Tenant also pays 11% taxes + a $1,000 non refundable seasonal reservation fee that covers the HOA application fees, departure cleaning fee, rental incidentals and booking fees. ½ of the total rents + taxes are due now upon signing the lease and the final ½ is due 120 prior to check in.
#226020077

NAPLES

8795 Calypso CT

3 Beds

2 Baths

2,406 Sq.Ft.

$20,000

MLS#: 226020077

New on site 4 days ago
Located inside the gated community of Summit Place, this inviting 3-bedroom, 2.5-bath townhome offers the perfect blend of comfort, functionality, and peaceful living in North Naples. Step inside and you’ll immediately notice the warm and welcoming layout designed for everyday living and easy entertaining. The first floor features tile flooring throughout the main living areas, creating a clean and cohesive feel, while the open-concept design allows the kitchen, dining, and living spaces to flow effortlessly together. Slide open the doors to the spacious screened lanai and enjoy your own private outdoor retreat surrounded by lush greenery — the perfect place to sip your morning coffee, unwind after a long day, or simply enjoy the quiet backyard setting with no rear neighbors in sight. Upstairs, all three bedrooms are thoughtfully tucked away for added privacy, including the comfortable primary suite and guest bath. Soft carpet flooring in the bedrooms adds warmth and comfort, while the first floor laundry room, half bath, and attached 1 car garage make daily life convenient and practical. Whether you’re looking for a full-time residence, seasonal getaway, or low-maintenance lifestyle in Naples, this home places you inside a resort-style community offering amenities such as a clubhouse, pool, spa, fitness center, tennis, pickleball, basketball courts, playground, and more — all just minutes from shopping, dining, and everything North Naples has to offer.
#226019624

NAPLES

15208 Summit Place CIR

3 Beds

2 Baths

1,667 Sq.Ft.

$395,000

MLS#: 226019624

WOW!!! Fantastic North Naples waterfront home within walking or biking distance to Barefoot Beach and 15 minutes to open water via Wiggins Pass with no bridges. Located in Little Hickory Shores, this home has been extensively updated with concrete block construction, impact windows, shuttered lanai, newer tile roof, newer heated pool with marble deck, and a newer walk-around dock with 13,500 lb lift and covered canopy. Flexible 2+Office/Private Sitting Room's and 2 Bath layout with spacious master suite offering an additional private space. Baths have been updated with tile, cabinetry, and surfaces; the kitchen features upgraded cabinetry, appliances, and finishes. Outdoor living includes a covered lanai, large sun deck, and generous dock space ideal for entertaining or relaxing. Enjoy boating or kayaking directly to nearby waterfront restaurants. Coveted Collier County location with lower taxes, A-rated schools, and resident beach access. One or more photo(s) has been virtually staged, AI generated or rendered.
#226019635

BONITA SPRINGS

225 3rd ST

3 Beds

2 Baths

1,753 Sq.Ft.

$999,000

MLS#: 226019635

One or more photo(s) has been virtually staged, AI generated or rendered. Step into this beautifully renovated home on 2.27 private acres where nearly everything has been updated from top to bottom! Located at 741 9th St SW, this 3-bedroom, 2-bath property feels like new construction with extensive upgrades throughout. Enjoy peace of mind with a newer roof, fresh interior and exterior paint, all new lighting, fans, fixtures, faucets, vanities, toilets, flooring, cabinets, quartz countertops, and stainless steel appliances. Built in 1996, but the stylish modern interior tells a completely different story. The spacious 2-car garage features durable epoxy flooring, while the newly screened lanai offers the perfect place to relax and enjoy the peaceful surroundings. Outside, the long paved circular driveway, mature trees, and lush landscaping create a welcoming first impression with plenty of privacy and charm. A small 2-stall barn in the backyard adds extra versatility for storage, hobbies, or animals. Enjoy the perfect blend of quiet country-style living with plenty of room to spread out, while still being conveniently close to shopping, dining, and everything town has to offer!
#226019319

NAPLES

741 9th ST SW

3 Beds

2 Baths

1,854 Sq.Ft.

$624,888

MLS#: 226019319

Experience easy Florida living in this newly built home located in a popular and convenient area of Port Charlotte. Set on a nicely positioned homesite with a peaceful, natural backdrop, this thoughtfully designed 3-bedroom + den, 3-bath residence offers a bright, open layout with high ceilings, abundant natural light, and high end modern finishes throughout. The kitchen features stylish cabinetry, stainless steel appliances, and a spacious island perfect for gathering and everyday living. The private primary suite includes dual walk-in closets, a large bath with dual sinks and an oversized walk-in shower. The guest bedrooms are positioned separately and share a full bath, while a third bathroom with direct outdoor access serves perfectly as a future pool bath. The spacious backyard offers endless possibilities to create your ideal outdoor retreat, with plenty of room for a pool, expanded lanai, outdoor kitchen, or tropical landscaping surrounded by peaceful greenery. Additional features include porcelain tile flooring throughout, a two-car garage with epoxy-coated flooring, no HOA, and a convenient location close to shopping, dining, golf, and everyday essentials.
#226017401

PORT CHARLOTTE

17156 Eugene AVE

3 Beds

3 Baths

1,660 Sq.Ft.

$359,000

MLS#: 226017401

elcome to 8940 Colonnades Ct E, Unit 734, located in the sought-after gated community of San Mirage in Bonita Springs, Florida. This well-maintained third-floor condo offers a perfect blend of comfort, style, and convenience in an ideal Southwest Florida location. The open-concept living and dining area is bright and inviting, filled with natural light and extending to a private screened lanai—perfect for relaxing or entertaining. The kitchen features modern appliances, ample cabinetry, and a breakfast bar for casual dining. The primary suite offers a peaceful retreat with a walk-in closet and en-suite bathroom featuring a tub and shower combination. Additional conveniences include an in-unit washer and dryer and extra storage space. Residents enjoy resort-style amenities, including a large swimming pool with cabana area and a fully equipped fitness center. Conveniently located near Publix, Prado Stadium 12, dining, and shopping options, the property is also less than 15 minutes from Bonita Beach, offering easy access to Florida’s coastal lifestyle. A comfortable, well-located home that combines everyday convenience with resort-style living.
#226019525

BONITA SPRINGS

8940 Colonnades CT E 734

2 Beds

2 Baths

1,013 Sq.Ft.

$1,900

MLS#: 226019525

Located just 8 miles from Downtown Naples and the beautiful Gulf beaches, this upgraded first-floor coach home offers comfort, convenience, and relaxing long lake views in a desirable low-fee community. Featuring 3 bedrooms, 2 bathrooms, and a 1-car attached garage, the home has been meticulously cared for and thoughtfully updated throughout. The spacious primary suite overlooks the water and includes an updated dual vanity cabinet, a large walk-in shower, and a generous walk-in custom closet. The open living and dining areas create an inviting atmosphere, while the kitchen offers granite countertops, a breakfast area, built-in desk space, and plenty of functionality for everyday living. Additional highlights include crown molding, tile flooring throughout the entire home, electric hurricane shutters, an epoxy floor garage, and a built-in Murphy bed for added flexibility. Step out onto the tiled lanai and enjoy peaceful waterfront views year-round. Whether you’re looking for a seasonal retreat or full-time residence, this move-in ready home is an excellent opportunity in one of Naples’ most convenient locations. Schedule your private showing today!
#226015314

NAPLES

340 Robin Hood CIR 102

3 Beds

2 Baths

1,630 Sq.Ft.

$330,000

MLS#: 226015314

NOT AVAILABLE FOR JANUARY 2027, FEBRUARY 2027, MARCH 2027, AND APRIL 2027. Welcome to 3425 Grand Cypress Dr #102, an elegant vacation retreat nestled in the heart of Naples, FL. This charming ground-floor condo offers a serene escape surrounded by lush landscaping and the peaceful ambiance of a prestigious golf community. Inside, you'll find a spacious, open-concept living area with abundant natural light, high ceilings, and tasteful furnishings that create a welcoming atmosphere. The kitchen, equipped with modern appliances and ample counter space, flows seamlessly into the dining and living areas, perfect for relaxing or entertaining. The master suite is a private sanctuary, featuring a plush bed, walk-in closet, and an en-suite bathroom with dual vanities and a walk-in shower. A second bedroom offers comfort for additional guests or family members. Step out onto the screened lanai and enjoy your morning coffee while overlooking the scenic, manicured grounds. This home also boasts access to resort-style amenities, including a sparkling community pool, fitness center, and walking paths. Located just minutes from pristine beaches, high-end shopping, and fine dining, this rental provides the perfect blend of tranquility and convenience. Whether you're here to unwind or explore, 3425 Grand Cypress Dr #102 promises an unforgettable stay in paradise.
#226019324

NAPLES

3425 Grand Cypress DR 102

3 Beds

2 Baths

1,763 Sq.Ft.

$6,500

MLS#: 226019324

Welcome to stylish, easy living in this new 3-bedroom + den, 3-bath home set on a quiet street in a convenient and popular area of Port Charlotte. With 1,677 square feet of well-planned space, this home offers a comfortable balance of openness and functionality. The main living area features an easy, open flow with high ceilings and abundant natural light, creating a bright and inviting feel. The kitchen is both stylish and practical, complete with modern cabinetry, stainless steel appliances, higher end details and a large island that naturally brings everyone together. The layout is thoughtfully arranged, with a spacious primary suite offering duel walk-in closets and a generous private bath with dual vanities and a walk-in shower. The guest bedrooms are tucked away, providing a sense of privacy and separation, and are complemented by a well-placed full bathroom. A third bathroom with direct outdoor access adds flexibility and is ideal for future pool use. Tile flooring runs throughout for a clean, low-maintenance finish, and the epoxy floor attached two-car garage provides added convenience. Outside, the yard offers plenty of room to create your own outdoor space, surrounded by natural greenery, with endless possibilities to add a pool, outdoor kitchen, lounge area, or private backyard retreat tailored to your lifestyle. Located in a well-liked area known for its accessibility to shopping, dining, parks, and everyday conveniences, this home is a great option for full-time living, seasonal use, or investment.
#226018610

PORT CHARLOTTE

17165 Fallkirk AVE

3 Beds

3 Baths

1,677 Sq.Ft.

$355,000

MLS#: 226018610

4140 Looking Glass Ln #3815 is a move-in-ready 2-bedroom, 2-bath condo for sale in Winterpark, one of Naples’ established communities with resort-style amenities and a convenient location. Offered at $329,900, this updated Naples condo features a fully redesigned kitchen with white cabinetry, stainless steel appliances, a stylish backsplash, large breakfast bar, and an open layout connecting the kitchen, dining, and living areas. The interior has a clean coastal feel with updated flooring, recessed lighting, modern finishes, and a spacious living room overlooking a peaceful outdoor setting. The owner’s suite includes custom closet space and an updated bathroom with a walk-in shower. The second bedroom and bathroom provide flexibility for guests, seasonal use, or a home office. A standout feature is the custom laundry and wine cellar area, adding valuable function and a unique touch. Winterpark amenities include a resort-style community pool, clubhouse, community room, pickleball, tennis, bocce court, bike and jog path, bike storage, extra storage, and internet access. The HOA includes cable, insurance, internet/WiFi access, irrigation water, lawn and land maintenance, reserves, sewer, street lights, street maintenance, trash removal, and water. For buyers searching for Naples condos for sale, a move-in-ready condo in Winterpark, or a well-updated property near shopping, dining, beaches, and downtown Naples, this is a strong opportunity.
#226019156

NAPLES

4140 Looking Glass LN 7

2 Beds

2 Baths

1,246 Sq.Ft.

$329,900

MLS#: 226019156

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

Enjoy nearly 2,600 sq. ft. of comfortable living space in this 4-bedroom plus den, 2.5-bath residence. Positioned on a lakefront lot, this home offers a functional great room floor plan featuring 9ft ceilings and tile/wood-look flooring throughout—no carpet! The kitchen is designed for easy gatherings with a breakfast bar, nook, and adjacent formal dining area. The second floor hosts oversized bedrooms, including a generous primary suite with dual walk-in closets and a bathroom featuring dual sinks, a soaking tub, and a separate shower. Significant mechanical peace of mind is provided by a BRAND NEW AC unit. Outdoor living is a breeze on the full-length screened lanai, featuring a heated saltwater pool and spa. While privacy plantings currently frame the backyard, the property boasts a direct lakefront position. Additional features include a 2-car garage with epoxy flooring, tile roof, storm shutters, and wiring for outdoor lighting. Orange Blossom Ranch residents enjoy a premier amenity package: 2 resort pools, 2 spas, fitness center, tennis, basketball, splash pad, and a social clubhouse. A large-scale floor plan in a prime Naples location with major updates already handled.
#226018258

NAPLES

2063 Sagebrush CIR

4 Beds

2 Baths

2,598 Sq.Ft.

$549,900

MLS#: 226018258

Annual rental condo available in the Bayshore Arts District! This ground-floor two bedroom, two bathroom condo located in Abaco Bay is only a short distance to all of the areas best amenities including Sugden Regional Park, Naples Botanical Gardens, East Naples Community Park, Bayview Park & Boat Ramp, Celebration Food Truck Park, Ankrolab Brewery, Rebeccas, and is less than 10 minutes from Downtown Naples. Unit has a combo washer/dryer in it. Abaco Bay offers a community pool, community laundry room, and a BBQ picnic area. No pets allowed. One person per application must meet the credit score requirement of 675 per HOA guidelines.
#226018789

NAPLES

4617 Bayshore DR H5

2 Beds

2 Baths

886 Sq.Ft.

$1,700

MLS#: 226018789

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