All Available Rental Properties

MLS Number O6191160

• Rental
• Mls Status Active
• Area Winter Park
• Subdivision Cloister Grove Sub
• Square Feet 8,353

Welcome to an unparalleled rental opportunity in Winter Park's prestigious Via Tuscany. Situated minutes away from the charming boutiques and eateries of downtown Park Avenue, this lakefront estate stands as a beacon of timeless elegance and historic significance. This distinguished property, dating back to 1919 and embodying the classic Georgian Revival style, occupies an impressive 1.57-plus acres gracefully perched above the tranquil waters of Lake Maitland. With 138 feet of coveted water-frontage, every moment here is adorned with breathtaking vistas from dawn to dusk. Immerse yourself in the grandeur of yesteryears seamlessly blended with modern comforts. Adorned with mature landscaping and a park-like backyard, this estate offers an enchanting ambiance for leisure and entertainment. Discover the allure of a gazebo, a sprawling lawn leading to the lake, a boat dock, an outdoor fireplace, and a captivating screened indoor pool. Step through the grand entry foyer into a world of refined living spaces, perfect for both intimate gatherings and lavish events. The first floor boasts an oversized living room, a formal dining room, a den, a study, a fully equipped kitchen, a breakfast room, a butler's pantry, and two sun porches. Ascend the dual staircases to find five bedrooms, four full baths, and numerous flex spaces, all adorned with timeless finishes and thoughtful details. The luxurious owner's suite exudes opulence, featuring a fireplace, a sitting area, oversized walk-in closets, a small bar area, elevator access, a private porch, and a rooftop terrace. Additionally, a charming guest cottage awaits, complete with a bedroom, a bath, a living room, and a kitchen, offering privacy and comfort to visitors. Ample storage is provided by the expansive attic and basement, complementing the four-car garage. With soaring ceilings, heart pine floors, plantation shutters, intricate millwork, and crown molding, every corner of this estate exudes sophistication and craftsmanship. Meticulously maintained and cherished, this property stands as a testament to quality and pride of ownership. With a total of 8,353 heated square feet, including 7,367 square feet in the main house and 986 square feet in the guest cottage, this residence offers unmatched living space in an unrivaled location. Seize the opportunity to experience the epitome of luxury living in Winter Park's most esteemed enclave.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6257763

• Rental
• Mls Status Active
• Subdivision Golden Oak
• Square Feet 6,704
• Year Built 2020

Experience the unparalleled luxury of Golden Oak at Walt Disney World® Resort! Situated in one of the most coveted locations, this fully furnished exquisite 5-bedroom, 5.5-bath estate spans 6,704 square feet of thoughtfully designed living space, blending sophistication and comfort throughout is now available 2/15/25-10/15/25. The moment you enter through the custom wrought iron front door, you're welcomed by a grand foyer with soaring ceilings, a formal seating area, and expansive windows that showcase breathtaking views of the pool and spa. The open-concept layout creates a seamless flow between spaces, enhancing the home's bright and airy ambiance-ideal for both relaxation and entertaining. The chef's kitchen is a true masterpiece, featuring sleek granite countertops, a premium Wolf gas range, and a wet bar complete with a wine cooler-perfect for hosting gatherings. The kitchen effortlessly transitions into the spacious family room, where soaring cathedral ceilings amplify the sense of space and light. Sliding glass doors open to the expansive outdoor Florida room, where a fully equipped summer kitchen awaits. Outfitted with granite countertops, a gas grill, mini fridge, and an adjacent gas fireplace, this area exemplifies the best of indoor/outdoor living. A convenient half-bathroom further enhances the functionality of the space, while the serene poolside setting offers an idyllic spot for unwinding or entertaining. The primary suite serves as a private retreat, offering tranquility and seclusion. Large windows flood the room with natural light, while the spa-inspired bathroom features dual vanities with striking granite countertops, an oversized walk-in shower, and a luxurious freestanding soaking tub. The custom walk-in closet is a showstopper, with a center island and abundant storage, keeping everything perfectly organized. The first floor also includes a spacious office and a well-appointed laundry room for added convenience. Upstairs, a bonus room with a pool table provides an entertaining haven, while three additional bedrooms, each with en-suite bathrooms and walk-in closets, ensure privacy and comfort for family members or guests. Designed with both luxury and functionality in mind, this home seamlessly integrates expansive living areas, refined finishes, and effortless transitions between indoor and outdoor spaces. It strikes the perfect balance between modern elegance and family-friendly comfort. The world-renowned Four Seasons Resort Orlando is just steps away, offering a golf course, spa, Michelin-starred dining, and concierge services. Schedule your private tour today!

Listing Courtesy of STOCKWORTH REALTY GROUP

MLS Number A4635279

• Rental
• Mls Status Active
• Subdivision Rosedale Add Ph Ii
• Square Feet 2,502
• Year Built 2017

***AVAILABLE STARTING APRIL 1, 2025*** Incredible opportunity to enjoy the MAINTENANCE-FREE Country Club lifestyle in the sought after Gated community of Rosedale! This gorgeous 3 Bedroom/3.5 Bath Single Family home in the Links subdivision of Rosedale is FULLY FURNISHED and is available for an annual lease, seasonal rental, or short-term (60-day minimum) residency. This gorgeous WCI home is upgraded throughout and includes absolutely everything you will need to move right in! Hardwood floors, mounted flat screen televisions, stainless steel appliances, granite countertops, and so much more! The open floorplan is PERFECT for entertaining and features a tastefully upgraded kitchen overlooking the great room. Enjoy your morning coffee from the breakfast bar area or take it outside and sit on your screened-in porch overlooking one of Rosedale's beautiful ponds! The home features 3 full bedrooms (each with their own private bath) and a separate den/office area! There is plenty of storage throughout including an over-sized attached 2-car garage. The laundry room comes complete with washer, dryer, and additional cabinet storage. The large Master Suite features a huge walk-in closet and en-suite bathroom with double sinks and a large walk-in shower. Your rent includes LAWN MAINTENANCE, FIBER OPTIC Hi-Speed Internet/TV service, 2 Dog Parks, and access through both of the 24-hour manned gates here at Rosedale! This is MAINTENCE-FREE living at its very best! A social membership to Rosedale Golf & Country Club is available (OPTIONAL) and includes a Full Social Calendar, Jr. Olympic sized pool, 5 Lighted Har-Tru Tennis Courts, Championship 18 Hole Golf Course, Driving Range, 2 Putting Greens, New State-of-the-art Gym Facilities, Clubhouse with full bar & restaurant, Outdoor Dining Patio, Private Fitness Classes, Personal Trainer, Yoga Studio, Outdoor Pool-side Yoga Area, Golf and Tennis Leagues, Private and Group Golf and Tennis Lessons, Bocce Ball Court, and the "19th Hole" featuring Billiards, Poker, Darts, and Shuffleboard! You simply can't beat the location! Rosedale is located near the intersection of 70/75 - so, everything you will need is nearby! Some of the most beautiful beaches in the country are all easily accessible, including St. Pete Beach, Clearwater Beach, and Siesta Key! Boating, Fishing, World Class Restaurants, and so much more!! This is FLORIDA living at its absolute finest!! This home is available for short and/or long-term rentals. Rates are reflected below: Annual Rental: $3500/Month - Tenant Pays Electric, Water, Sewer, Gas Off-Season Rental (May - November): $4600/Month - All utilities included in rent. In-Season Rental (December - April): $6500/Month - All utilities included in rent. Any lease 6 months or less in duration is subject to 13% state/county tax. Leases longer than 6 months are exempt from taxes. 2025 Months Available: APRIL, MAY, JUNE, JULY, AUGUST, SEPTEMBER, OCTOBER, NOVEMBER, DECEMBER. 2026 Months Available: JANUARY, FEBRUARY, MARCH, APRIL, MAY, JUNE, JULY, AUGUST, SEPTEMBER, OCTOBER, NOVEMBER, DECEMBER.

Listing Courtesy of NETWORK REAL ESTATE GROUP

MLS Number O6248632

• Rental
• Mls Status Active
• Square Feet 6,441
• Year Built 2004
• Bedrooms 4

Introducing a rare opportunity to own a unique lakeside property on Lake Maitland, part of the prestigious Chain of Lakes. This magnificent estate boasts 100 feet of water frontage and comes fully furnished, making it turnkey ready. Spanning over 6,400 square feet, the tastefully designed interior features four bedrooms, five-and-a-half baths, a bonus room, a home office, a gourmet kitchen, and a wine cellar. The elegant formal living room with a fireplace and the formal dining room set the stage for sophisticated entertaining. The gourmet kitchen is equipped with Sub-Zero appliances, a gas range, granite countertops, and offers stunning water views. Throughout the home, you'll find beautiful travertine flooring, vaulted ceilings with wood beams, crown molding, and custom built-ins. Upstairs, the primary suite offers the most breathtaking views of the lake, complemented by an adjoining home office or additional bedroom for added convenience. Three additional bedrooms with en-suite baths and ample closet space complete the upstairs living quarters. Outside, the private backyard features a screened-in patio, a sparkling swimming pool, a hot tub, and meticulous landscaping. A covered boat dock with a lift provides easy access to the lake. Additional highlights include a three-car garage, a private gate for enhanced security, and recent upgrades such as a new roof, AC units, and copper gutters. Don't miss this unparalleled opportunity to embrace lakefront living on the Winter Park Chain of Lakes, where property availability is exceptionally rare. Enjoy stunning sunrise and sunset views from your own slice of paradise

Listing Courtesy of SOUTHERN REALTY GROUP LLC

MLS Number OM689702

• Rental
• Mls Status Active
• Area Ocala
• Subdivision Kimberwood Farms
• Square Feet 3,181

Your winter home away from home! Spectacular 10 acre farm just steps away from the renowned World Equestrian Center and Golden Ocala Golf Club. This turnkey farm has everything to make your winter circuit successful, including a beautiful 4 bedroom, 3 bathroom custom designed residence nestled among lush landscaping and live oak trees with a relaxing outdoor living space. The facility includes an impeccable 10 stall center aisle stable with 12 x 12 stalls, two large indoor wash racks, feed room, lounge, full bathroom, tack room, fly spray system and storage area. You will also find two outdoor wash areas, and all weather footing paths in the horse traffic areas leading to the 6 horse eurocizer complete with irrigation and footing as well. Your horses will enjoy 6 large grassy paddocks, as well as the option to work and exercise in the all weather footing arena OR the large turf field that are both completely irrigated. The farm has a private gated driveway to the residence and a separate gated entrance to the stables. Don't miss this special opportunity and location!

Listing Courtesy of GOLDEN OCALA REAL ESTATE INC

MLS Number A4616271

• Rental
• Mls Status Active
• Subdivision Harbour Walk
• Square Feet 4,711
• Year Built 2006

Are you ready for your boating vacation??? Here is a rental with a dock and boat lifts... take a look at this spectacular waterfront property in the exclusive gated community of Harbour Walk off of the Gulf Coast of Southwest Florida, on the south side of the Manatee River with direct access to the Gulf of Mexico. This property offers 103' of saltwater canal with a 65' dock and 2 boat lifts: one 10,000 lb lift and one 5,500 lb lift. A sanctuary for water enthusiasts, this property promises effortless indulgence in the adventures of each passing day, which end with mesmerizing sunsets. Distinguished by its location on the even-numbered addresses of Fore Drive, be spoiled by unhindered river access sans the need for locks. Enjoy a short easy boat ride from the canal through the 6' deep channel, to the Manatee River, out to the beautiful waters of the Gulf of Mexico that is lined with soft powdery white sandy beaches. Within this exclusive residence, an expanse of living space reveals itself, offering a recreation room, a theatre, two balconies, and a double-story screened lanai with marble pavers, outdoor kitchen, heated pool & spa. Conveniently located near downtown Bradenton, Lakewood Ranch, Sarasota, St. Petersburg, and Tampa, this home is located in close proximity to three airports, wonderful shopping, gourmet dining, cultural attractions, the esteemed IMG Sports Academy and 3 major hospitals. Embrace an array of outdoor adventures, from year-round fishing and golfing to hiking and biking, all within easy reach. Welcome to your sanctuary in Southwest Florida - an opulent two-story retreat inviting you to savor a lifestyle brimming with relaxation and/or play. This home could be yours...come see, come sigh and make this exclusive canal front property in Harbor Walk your own.

Listing Courtesy of KELLER WILLIAMS ON THE WATER S

MLS Number O6256452

• Rental
• Mls Status Active
• Area Windermere
• Subdivision Sunset Bay
• Square Feet 5,802

Welcome to 5000 Down Point Lane in Windermere, a luxurious retreat situated on 2 acres of pristine lakefront property. This entirely renovated home offers breathtaking sunsets over Sunset Bay, providing a picturesque backdrop for daily living. The master suite, office, entertainment room and an additional suite are conveniently located on the main floor, while three more bedrooms and bonus room are upstairs. Cozy up by the fireplace in the spacious living area, or enjoy the elegance of Italian porcelain flooring throughout the home. Outdoor living is elevated with a large pool patio and entertainment area, complete with a summer kitchen. The expansive grassy yard leads up to your private beach and dock, perfect for enjoying the best of lakefront living. At just under 6,000 square feet, this home offers ample space for comfort and luxury. Don't miss the opportunity to live in this spectacular property in Windermere!

Listing Courtesy of SOUTHERN REALTY GROUP LLC

MLS Number O6216237

• Rental
• Mls Status Active
• Area Winter Park
• Subdivision Virginia Heights
• Square Feet 3,181

A one-of-a-kind character home in Winter Park, rich in Winter Park history - indulge in the epitome of luxury living with this exquisite rental on Lake Virginia, part of the renowned Winter Park Chain-of-Lakes. This unique character home, completely renovated by E2 Homes, offers an unparalleled blend of elegance, comfort, and modern sophistication. Step inside to discover gorgeous interiors featuring a modern kitchen equipped with Gaggenau appliances, sleek cabinetry, and bar seating. French doors open to a covered back deck, providing breathtaking views of the heated salt-water pool and Lake Virginia. The main house boasts three beautifully appointed bedrooms and two and a half baths, all fully furnished with high-end furniture pieces and designer finishes. The second floor primary suite features hand-painted wallpaper by de Gournay and a private Juliet balcony allowing breathtaking views of the grounds and Lake Virginia. The formal dining room is artfully designed, with French doors and arched windows revealing a serene green vignette side patio space. The living room, with its large picture windows, offers views of the side patio and features a cozy fireplace. Built-in shelves frame the entrance to the sun-drenched Florida room, perfect for soaking in the natural light. Adjacent to the main house, the detached pool cabana house offers a private retreat. This beautifully furnished space includes a full bedroom, a full bath, a comfortable sitting area, and a kitchenette. Floor-to-ceiling picture windows allow for an abundance of natural light and peaceful views of the meticulously groomed backyard and pool. The outdoor space is a true haven, featuring a covered deck that overlooks the heated saltwater pool, the detached guest cabana, the covered boat dock and expansive views of the lake. This one-of-a-kind luxury rental is offered completely furnished, ensuring a move-in ready experience for discerning tenants. Embrace the ultimate in lakefront living on Lake Virginia, where every detail has been thoughtfully designed to provide an extraordinary lifestyle.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number A4575730

• Rental
• Mls Status Active
• Area Bradenton
• Subdivision Tidy Island Ph Ii
• Square Feet 3,069

AVAILABLE from 05/01/2024 through 2025 Season Price shown is the Dec-April price. Call for off-season pricing. Spectacular sun-drenched Seasonal Rental offered in the gated exclusive Tidy Island Community. An immaculate, fully renovated Bayfront retreat with breathtaking water and sunset views, designer furnishings, beautifully manicured landscaping, and nature galore. This modern luxury home is one of the largest townhomes within Tidy Island and has three bedrooms ,2 1/2 baths along with a loft area. You enter the home on the ground level to a breathtaking large foyer and staircase. There is a ground floor garage and large screened-in area. One flight up is the main floor with high ceilings and stunning bay views throughout. Large screened- in lanai fully furnished to enjoy outdoor dining as well as the gorgeous panoramic water view. The Great Room has fabulous oversized sofas, comfortable swivel chairs, and a brand new large smart T.V. Large Dining space has Bay views and and eat-in "state of the art" Kitchen with additional dining/work space. Master Bedroom offers a King size bed ,spacious en-suite full Bath with garden bath and large walk-in shower. A Powder Room and full Laundry Room are also on the main floor. The Loft offers a large seating area/work space ,an 85" TV and gorgeous views. 2 guest bedrooms ,both with Queen beds and a full guest bath complete the upper level. Tidy Island offers five star resort-style amenities. Tenant application fee of $100 allows use of all amenities. The clubhouse has a fitness room, waterfront pool, lap pool and spa and 2 Har-Tru tennis courts and nearby pickle ball courts .Tidy Island has 240 acres of Nature Preserves ,a bird Sanctuary, on site walking trails, ponds, Bay access for kayaks and canoes, and its own archaeological museum. This rental offers unrivaled peace and tranquility yet is only minutes from all conveniences - shopping, restaurants, beaches and parks. Close to IMG Academy, Sarasota, and Ana Maria island. A true gem! The Elevator is Not offered. 1 small dog may be allowed at owners discretion. No smoking allowed. 1 car will remain in the garage allowing tenant to have 1 space.

Listing Courtesy of JENNETTE PROPERTIES,INC.

MLS Number O6236631

• Rental
• Mls Status Active
• Area Windermere
• Subdivision Casabella Ph 2
• Square Feet 6,881

Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half acre lot, this remarkable home presents an unparalleled opportunity to experience the epitome of high-end living. As you step inside, you'll be greeted by an aura of sophistication that permeates every corner of this lavish residence. With 6 generously appointed bedrooms and 6 full bathrooms accompanied by 2 half baths, there is no shortage of space for both family and guests. The residence boasts a thoughtfully designed layout that effortlessly combines practicality with aesthetics. The heart of this home is its modern kitchen, complete with top-of-the-line appliances and an oversized kitchen island, perfect for culinary enthusiasts and those who love to entertain. Seamlessly flowing from the kitchen is a spacious living area adorned with luxurious finishes, creating an inviting atmosphere for relaxation and social gatherings. A standout feature of this home is the bonus room, offering versatile space for a home office, entertainment center, or a personal gym - the possibilities are endless. The 3-car garage provides ample storage for vehicles and more. Step outside to your own private oasis, where a meticulously landscaped backyard awaits. The summer kitchen offers an ideal setting for outdoor dining and entertaining, while the lush greenery and serene surroundings provide a sense of tranquility. The oversized pool takes center stage, beckoning you to indulge in a refreshing dip or bask in the sun-kissed luxury. This residence is being offered fully furnished, allowing you to move in seamlessly and immediately begin enjoying the luxurious lifestyle it provides. Every detail, from the grand entrance to the intricate finishes, has been carefully curated to create an atmosphere of luxury and sophistication. Don't miss your chance to live in this unparalleled piece of Windermere's real estate. Schedule a private showing today to experience the grandeur and elegance of 3999 Isabella Cir firsthand.

Listing Courtesy of DELUCA REAL ESTATE SERVICES CORP

MLS Number OM680075

• Rental
• Mls Status Active
• Area Ocala
• Subdivision None
• Square Feet 3,200

!Available for short term or long term this fully turn key 4 bedroom 3 bathroom , with pool terrace , grill area 12 + acre Farm. just. 3 minutes drive to World Equestrian Center ! The farm boast a new fully drainage base 125 X250 Arena with GGT footing a 8 stalls center aisle concrete Barn with clay footing ,office /tack room , bathroom , laundry room with washer and dryer . 6 large paddocks, a shed barn , 2 RV hook ups Available from January 1st 2025 . Landlord will maintain grounds and internet . Priced for a year contract call agent for short term months price.

Listing Courtesy of THE KEYES COMPANY

MLS Number O6258654

• Rental
• Mls Status Active
• Area Windermere
• Subdivision Casabella Ph 2
• Square Feet 7,337

Welcome home! This luxurious residence is located in the Casabella in Windermere. Casabella features 79 exclusive luxury homes and private gated entry. This Toll Brothers community features half acre home sites, two beautifully designed ponds with fountains and a playground area, 4012 Isabella Circle is the Villa Lago Floor plan with Coastal Elevation features unparalleled details and upgrades throughout, from the premium Lot with fountain and water views, custom light fixtures, to the breathtaking stone floors Throughout, luxurious hardwood floors , upgraded outdoor kitchen, upgraded master bathroom with his and her bathroom, upgraded “open riser” stair case, coastal elevation with balconies, exterior travertine flooring, custom design infinity edge pool with breathtaking water views, upgraded shelving closets Throughout. The chef inspired kitchen includes top of the line subzero and wolf appliances, modern custom cabinetry, and a massive center island that's perfect for hanging out with family. The home features 6 large suites plus an office and an oversized bonus room upstairs great for gaming and studying and also connecting to a home movie theater, each suite has its own bathroom including an expanded first floor master with a separate sitting area, work out room, his and hers closets, and oversized walk-through shower with his and her bathroom. Additionally, this home comes with 4 car garage. The moment you step through the front doors your eyes are greeted by soaring two story ceilings, a wall of windows overlooking the infinity edge pool and pond, and an abundance of architectural details. A huge, covered lanai with an upgraded summer kitchen with that includes, gas grill, refrigerator, ice maker, and an enormous outdoor dining area. Energy saving and organic with low E double panel windows, thankless hot water heaters, spray foam insulation and many building features to enhance living enjoyment. The 4-car garage allows for extra car parking, storage or boat storage. Lawn care and pool maintenance included!

Listing Courtesy of METROPOLITAN R.E SOLUTIONS INC