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Welcome to your Naples retreat at 4290 Gulfstream Drive, #5 — an inviting annual rental offering comfort, convenience, and the laid-back Florida lifestyle. Nestled in a desirable location just minutes from Naples’ world-renowned beaches, shopping, dining, and entertainment, this residence provides the perfect balance of tranquility and accessibility. Enjoy a bright and airy interior filled with natural light, complemented by an open and functional layout ideal for both everyday living and entertaining. The home features well-proportioned living spaces, comfortable bedrooms, and a thoughtfully designed kitchen ready for your culinary needs. Step outside and take advantage of the community’s peaceful surroundings, perfect for relaxing after a day exploring all that Naples has to offer. Whether you're looking for a long-term home base or a comfortable coastal escape, this annual rental delivers exceptional value in one of Southwest Florida’s most sought-after destinations.
#226005331

NAPLES

4290 Gulfstream DR 5

2 Beds

2 Baths

956 Sq.Ft.

$1,600

MLS#: 226005331

*This is a 55+ community, tenants must be 55 years old or older to live here.* This beautifully maintained end-unit 2-bedroom, 2-bath rental offers the perfect blend of comfort and convenience, located just moments from downtown 5th Avenue, restaurants, shopping, and Naples’ pristine beaches. Inside, you’ll find new flooring throughout the main living areas and bedrooms—no carpet here—along with elegant crown molding and two inviting sunrooms, one at the front and another off the guest bedroom, ideal for relaxing or entertaining. The master bedroom provides a restful retreat with its generous king bed and comfortable mattress. The guest room is furnished with a queen bed. Both bedrooms are furnished with dressers, closets, and plenty of storage space. This unit is close to the pool yet tucked away for privacy, and features the ease of an in-unit laundry so you can skip the common area. With thoughtful updates and a move-in-ready design, this retreat is ready to be enjoyed.
#225083112

NAPLES

300 Valley Stream Dr A7

2 Beds

2 Baths

979 Sq.Ft.

$1,600

MLS#: 225083112

Welcome to this inviting annual rental in the heart of Naples, offering comfort, convenience, and the relaxed Southwest Florida lifestyle. Located at 194 Santa Clara Drive #194-3, this well-maintained residence provides a bright and functional living space designed for easy everyday living.

The home features a thoughtfully arranged layout with spacious living areas, abundant natural light, and a warm, welcoming atmosphere throughout. The kitchen offers ample cabinetry and workspace, flowing seamlessly into the main living and dining areas—ideal for both quiet evenings at home and casual entertaining. Generously sized bedrooms provide comfortable retreats, while the overall design emphasizes practicality and livability.

Enjoy a desirable location close to shopping, dining, major roadways, and all that Naples has to offer, including beautiful beaches, golf, parks, and vibrant local attractions. This property presents an excellent opportunity for tenants seeking a well-situated, long-term rental in a sought-after area.
#226008248

NAPLES

194 Santa Clara DR 194

1 Beds

1 Baths

833 Sq.Ft.

$1,600

MLS#: 226008248

Available for Rent Now Totally remodeled home. Newer appliances, floors, everything redone !! Lots of light. Huge backyard and all fenced in. Pets OK with pet deposit.
#226007567

LEHIGH ACRES

3820 20th ST W

3 Beds

1 Baths

1,000 Sq.Ft.

$1,395

MLS#: 226007567

This office has an attractive reception area and offices of various sizes which would accommodate many types of businesses.  At this price, a tenant could have room to grow.  Break Room and Storage rooms.
This is a Sublease and the lease rate is extremely competitive even with other spaces in the same complex.  Tax is paid on all FL leases and the CAM is a moderate $3.83 SF or $798.19 monthly on the entire space.
#214035374

NAPLES

3765 Airport Pulling N RD 201

None Beds

None Baths

N/A

$10

MLS#: 214035374

Current Tenants are extremely motivated to Sub-Lease this ready to occupy space !!! There is one office suite remaining  with 1,182 sq foot. All reasonable offers will be considered. Very nice office space in the growing South Naples area. The suite features both open cubicle areas, as well as several private offices. A longer term lease could possibly be negotiated with the Owner upon completion of the Sub-Lease in September 2022.
#220067000

NAPLES

12330 Tamiami Trail East TRL 102

None Beds

None Baths

3,720 Sq.Ft.

$0

MLS#: 220067000

Gordon Pointe. The most unique, exceptional offering in Florida, and quite possibly the entire United States. The capstone of the storied Gordon Drive in Port Royal, Naples FL. Located on the southern tip and consisting of 3 residences, Gordon Pointe encompasses over 9 acres offering 722' of pristine, white sand beach. A true peninsula, this legacy estate offers both protected harbor with its' one-of-a-kind, private 231', deep water yacht basin, additional 111' foot floating t-dock, captivating Naples Bay views, and absolutely stunning vistas of the Gulf of America. Anchored in place and moored in legacy, Gordon Pointe possesses a rare combination of scale, privacy, and protected harbor. A once in a generation opportunity to acquire the ultimate estate.
#226009175

NAPLES

100 Bay RD

None Beds

None Baths

22,800 Sq.Ft.

$271,000,000

MLS#: 226009175

Gordon Pointe. The most unique, exceptional offering in Florida, and quite possibly the entire United States. The capstone of the storied Gordon Drive in Port Royal, Naples FL. Located on the southern tip of Gordon Drive, 100 and 104 Bay Rd encompasses over 5 acres offering 722' of pristine, white sand beach. This legacy, beachfront estate offers the option of protected harbor in the 231' Yacht Basin, captivating Naples Bay views, and absolutely stunning vistas of the Gulf of America. Anchored in place and moored in legacy, Gordon Pointe possesses a rare combination of scale, privacy, and protected harbor. A once in a generation opportunity to acquire the ultimate estate.
#226014932

NAPLES

100 & 104 Bay RD

None Beds

None Baths

5.39 acres

$195,000,000

MLS#: 226014932

This is the center parcel of one of the largest beachfront properties in the United States. Together, the three properties span over 15 acres with 800 feet of Gulf frontage - offering a once in a lifetime opportunity to build a true legacy estate in the esteemed Port Royal area.
#223017155

NAPLES

2200 Gordon DR

6 Beds

13 Baths

8,846 Sq.Ft.

$175,000,000

MLS#: 223017155

A once-in-a-generation opportunity in the heart of Aqualane Shores.
Encompassing nearly 4 acres across 7 contiguous lots, this extraordinary waterfront assemblage offers an unmatched 858 feet of continuous water frontage along a deepwater canal and Naples Bay. A true rarity in Naples, it combines panoramic bay views, direct Gulf access with no bridges, and three grandfathered-in boathouses - making it both a boater’s paradise and a developer’s dream. The site is nearly cleared and ready for transformation, presenting the perfect canvas for a world-class private compound or multiple luxury estates. Situated just moments from the beach and Naples’ iconic Third Street South, this is among the largest and most significant land offerings ever presented in Aqualane Shores. A legacy property of rare scale and potential.
#225075672

NAPLES

820 Jamaica LN

None Beds

None Baths

4.08 acres

$89,995,000

MLS#: 225075672

Burgess Island is one of Florida’s most significant private island estates, conveniently positioned in Pine Island Sound between Sarasota and Naples. Spanning approximately 104 acres with extensive shoreline and unmatched privacy, the property presents an extraordinary opportunity for a singular private family compound, a corporate retreat, or an exclusive development, with its 29 developable lots. Centered around an updated 1920s Mizner-style residence, the island is complemented by four charming guest cottages, a clubhouse and pool, and a dedicated property manager’s cottage. There are a total of 11 bedrooms, 10 full and 3 half bathrooms across the island. Lifestyle amenities are equally compelling, featuring a private 9-hole golf course, a pickleball, tennis, and basketball sport court, along with four separate docks providing convenient water access. A helipad enhances accessibility, allowing seamless travel to and from the mainland. The level of infrastructure is rarely found in island offerings of this scale, including mainland power service, four onsite generators, and a reverse osmosis water system - providing both comfort and self-sufficiency. The property’s heritage is as remarkable as its physical attributes. Originally acquired in 1924 by renowned inventor and electrochemist Charles Frederick Burgess - a pioneer in dry-cell battery technology - the island has long been a destination for innovation and distinguished company. Thomas Edison himself visited and planted banyan trees that endure today as living landmarks of this legacy. Comprehensive amenities, flexible access, a convenient yet private location, and a storied past converge to make Burgess Island not merely a residence, but a rare and irreplaceable asset. Ideally positioned for the Southwest Florida lifestyle, the island offers immediate access to world-class tarpon fishing, exceptional boating, and kayaking through pristine waters, while remaining just moments from the historic Gasparilla Inn and championship golf. From your dock, cruise to Cabbage Key for a relaxed waterfront lunch or continue on to Boca Grande for an evening of dining and coastal charm—where nearby islands and waterways naturally extend the experience beyond the property. Located ~6 mi. to Gasparilla Inn & Golf Club, ~2 mi. Useppa Island, ~1 mi. to Four Winds Marina, ~5.5 mi. to Boca Grande Marina (Miller’s), ~11 mi. to Coral Creek Airport & Golf Club, ~19 mi. to Punta Gorda Airport (PGD), ~28 mi. to RSW, and ~45 mi. to Naples Airport (APF). The island is known as Little Bokeelia Island, Burgess Island, and Pentecost Island.
#226015871

BOKEELIA

X Burgess Island

6 Beds

10 Baths

11,371 Sq.Ft.

$89,000,000

MLS#: 226015871

You’ve earned it. Now enjoy it in paradise. Sit back on your tropical loggia listening to the surf, with dolphins cavorting just a few yards off the beach. Miles of beautiful white sand stretch away in both directions. Watch glorious sunsets that seem exclusive to Naples, Florida. With an average winter temperature in the low 70s, it is near perfect. The number one destination in the US. You have found the ultimate jewel; the only remaining entire city block on the beach. Nearly 3 acres on the Paradise Coast. This property has been maintained by the owner organically without pesticides for decades. Located a short 3 minute stroll to the world class shopping and restaurants of the historic 3rd Street South, a property like this comes only once in a lifetime; a unicorn. An incredible opportunity!
#224076721

NAPLES

20 14th AVE S

None Beds

None Baths

4,822 Sq.Ft.

$89,000,000

MLS#: 224076721

H.15240 - Beachfront luxury and the ultimate family compound never before on the market. Over 303 feet of gorgeous white sand beach of the Gulf of Mexico, boasting 3.98 lushly landscaped acres w/3 separate homes, & potential to subdivide this gated, tropical paradise. The Main home, Guest Home and Caretaker's Cottage. Breathtaking, unobstructed, westerly, forever views of the Gulf and sunsets. Exquisite finishes & materials imported from all over the world. The finest fixtures & unsurpassed craftsmanship, chef’s kitchen, luxurious first floor master suite, huge his/her closets w/built-ins, custom millwork, moldings, cabinetry and plaster throughout. Gulf side pool and spa. A 5-bay collector's garage. Full brochure available for extensive list of top quality features. Classic European estate, known as Villa Vista for its endless views. Eligible for Port Royal Club membership to enjoy the finest private club experience w/world-class dining, pristine beach w/club services, beachside pool, fitness, tennis, and spa facilities. Escape to paradise and bring the whole family!
#219077095

NAPLES

2700 Gordon DR

6 Beds

6 Baths

11,511 Sq.Ft.

$65,000,000

MLS#: 219077095

The original owners of this estate chose a Lowcountry style home architecture, one of the most distinctive elements of South Carolina and Georgia developed in the late 1700’s. It is still considered today to be the most efficient design for hot subtropical climates and coastal areas. These designs are typically elevated with raised first floors, inviting porches to enjoy the outdoors in the shade, underfloor spaces with lattice for storage/ parking, hipped roofs, columns/pillars, widow’s walks, large windows and doors that allow a cooling breeze to flow through. The finest team of craftsmen were assembled to create this breathtaking vision whose true success lies in its welcoming Presidents, huge charity events, casual family gatherings and private contemplation, all with the same grace and charm. An enchanting setting through ornate gates opens to stands of palm trees, verdant lawns and privacy hedges surrounding the main home, multiple guest facilities, pool, pool house, various garages and service buildings, and even your own ‘secret garden’.
#216026725

NAPLES

2500 Gordon DR

6 Beds

7 Baths

10,825 Sq.Ft.

$60,900,000

MLS#: 216026725

This is the northernmost parcel of one of the largest beachfront properties in the United States. Together, the three properties span over 15 acres with 800 feet of Gulf frontage - offering a once in a lifetime opportunity to build a true legacy estate in the esteemed Port Royal area.
#223017618

NAPLES

2170 Gordon DR

None Beds

2 Baths

3,518 Sq.Ft.

$60,000,000

MLS#: 223017618

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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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