Siesta Key Homes with Courtyard Exterior Features

Siesta Key Homes with Courtyard Exterior Features

Welcome to Siesta Key, Florida, a tropical paradise nestled in Sarasota County that is renowned for its stunning beaches, vibrant culture, and laid-back lifestyle. Known for its powdery white sands and crystal-clear waters, Siesta Key is a haven for sun-seekers, nature lovers, and anyone looking to embrace the quintessential Florida lifestyle. This enchanting barrier island offers an array of recreational activities, from kayaking and paddleboarding to exploring the lush local parks and nature reserves.

One of the most appealing aspects of Siesta Key is its diverse selection of homes, particularly those featuring charming courtyard exterior designs. These residences often boast inviting outdoor spaces that create a seamless blend between indoor and outdoor living. Imagine sipping your morning coffee in a tranquil courtyard surrounded by tropical landscaping, or hosting gatherings with friends and family in a sun-drenched patio area. The courtyard style not only enhances the aesthetic appeal of the home but also provides a sense of privacy and serenity that is hard to find elsewhere.

In Siesta Key, homes with courtyard features are designed to maximize the natural beauty of the surroundings while offering modern conveniences and luxurious finishes. Whether you’re looking for a cozy beach bungalow or a lavish estate, the courtyard homes in this idyllic locale provide the perfect backdrop for creating lasting memories. Experience the magic of Siesta Key living, where every day feels like a vacation, and your dream home awaits!

Newest Siesta Key Homes with Courtyard Exterior Features

6157 Midnight Pass Road Unit E93, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code
Exceptional opportunity on SIESTA KEY! Whether you're searching for a vacation getaway, full-time island residence, or income-producing investment, this TURNKEY 2-bedroom, 2-bath condo at Bay Oaks offers an unbeatable combination of location, flexibility and value. With WEEKLY RENTALS ALLOWED, owners have the freedom to take advantage of Siesta Key's highly desirable vacation rental market while still enjoying the property themselves. Outside rental management and self-management is allowed, providing added flexibility for investors. Located on the third floor, this spacious 1,101 sq. ft. condo is being sold TURNKEY and ready to enjoy from day one. The kitchen has been beautifully renovated creating a fresh, updated space with stainless steel appliances, gorgeous quartz countertops, large island with seating, and coastal backsplash. The open living and dining areas flow onto a screened in balcony overlooking mature tropical landscaping—the perfect spot to enjoy your morning coffee or unwind after a day at the beach. A generous outdoor storage closet provides convenient space for beach chairs, umbrellas and all your island essentials. The split bedroom layout offers privacy for owners and guests, with two spacious bedrooms and two full bathrooms. An IN-UNIT WASHER AND DRYER adds another sought-after convenience for both personal use and vacation rentals. Bay Oaks provides an impressive collection of amenities including a heated community pool, fishing pier along the Intracoastal Waterway, tennis and pickleball courts, BBQ and picnic areas, and covered parking. Leave the car behind and embrace the island lifestyle with the Siesta Key trolley providing convenient transportation to Siesta Key Village, local restaurants, shops, entertainment and Siesta Key's world-famous white-sand beaches. With weekly rentals permitted, flexible management options, turnkey furnishings, a renovated kitchen and an outstanding Siesta Key location, this condo offers an incredible opportunity to own your own piece of paradise while enjoying the potential for vacation rental income. Bring you sunscreen and come experience everything that makes Siesta Key one of Florida's most sought-after island destinations!

6157 Midnight Pass Road Unit E93, Sarasota

8773 Midnight Pass Road Unit 504G, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota

7535 Midnight Pass Road, Sarasota
$4,500,000
5 Beds ⋅ 2 Baths ⋅ Sub Of Us Lt 7 Of 20-37-18 SubDv. ⋅ 34242 Zip Code
For the first time since 1925, the same Sarasota family is bringing 7535 and 7539 Midnight Pass Road to market, offered together as nearly one acre on Siesta Key. The two parcels total 0.95 acres, with 7535 offering over 100 feet of direct waterfrontage on Little Sarasota Bay, a reinforced concrete seawall, and access to the Intracoastal Waterway. The main home was designed by Jack West, a celebrated architect of the Sarasota School of Architecture. The charming second home on the adjoining parcel was designed by his onetime partner, Elizabeth Boylston, the first woman in Florida elected to the American Institute of Architects. This second residence offers two bedrooms, one bathroom, and 1,016 square feet, in addition to the MLS-listed totals. A detached two-car garage provides additional parking and storage. Walls of sliding glass and graceful midcentury lines open the main house to the garden and the water. Framed by lush tropical greenery, the combined site presents a rare opportunity to create a waterfront compound with a main residence, guest house and gardens. An additional adjacent 0.53-acre lot may also be available for purchase at an additional price, offering an opportunity to expand the property even further. A 2016 dock with a 13,000 lb boat lift provides access to the Intracoastal Waterway, where mornings begin with soft golden light over Little Sarasota Bay. Turtle Beach, Crescent Beach, and the powder-soft white sand of Siesta Beach are minutes away, with Siesta Key Village, downtown Sarasota, and Sarasota Bradenton International Airport all within easy reach. For the buyer who has been waiting for the right piece of Siesta Key, this is it: nearly an acre of land with direct bayfrontage, a seawall, dock and lift already in place, complemented by an architectural legacy and history that cannot be replicated. Create the waterfront home you have always imagined on land that has been cherished by the same family for over a century and is now ready for its next chapter.

7535 Midnight Pass Road, Sarasota

5376 Shadow Lawn Drive, Sarasota
$2,400,000
5 Beds ⋅ 5 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Some homes on Siesta Key are about the beach. Others are about boating. This one lets you have both. Set along a protected canal with direct boating access to Sarasota Bay through the Grand Canal, and from there to the Intracoastal Waterway and the Gulf, this Siesta Key waterfront home is made for the way life is meant to be lived. Take the boat out for the morning, launch a kayak or paddleboard from your own waterfront, spend some time at Siesta Key Beach, then come home to your private saltwater pool, outdoor kitchen and quiet canal view. The important updates are already here too: a 2021 reroof, impact windows and sliders installed in 2022, plus new first floor flooring, fresh interior paint, a luxury renovation of the first floor primary bath, an outdoor kitchen and waterfront pavers, all completed in 2026. Plantation shutters finish every window and slider. At the center of the home, a fully screened courtyard lanai with a tabletop fire pit extends the living space. Seven impact sliders connect several rooms directly to the courtyard, filling the home with natural light and creating an easy indoor outdoor flow toward the pool and waterfront. Additional sliders from the flex room open toward the pool. The home and pool sustained no storm damage during the 2024 storms. If you haven’t dropped anchor yet, wait until you see the two amazing primary suites. The first floor primary offers courtyard access, two walk in closets and a beautifully renovated 2026 ensuite bath with upscale finishes. Upstairs, the entire second level becomes a private retreat with canal views, a spacious bath, two more walk in closets and its own waterfront balcony. One closet is so large you may wonder if it could qualify as a New York City apartment. When it is time for a little quiet, open the sliders and take in sunset over the canal, or start your morning with fresh air and coffee on the balcony. A redesigned media and flex area now includes an additional bedroom while preserving an approximately 424 square foot flex room for a media room, gym, game room or lounge. Another bedroom includes a Murphy bed and built in desk, making it an easy guest room, home office or both. Outside is where this home really earns its Siesta Key address. The private saltwater pool is surrounded by tropical landscaping and spaces for relaxing, dining and entertaining. The seawall, bulkhead and davits were replaced in 2021, with the waterfront setup planned around a 45 foot Sea Ray. This is a home for boaters who want to use the water, not simply look at it. Set in the heart of Siesta Key, the home is just minutes from Siesta Key Beach, named the No. 1 in the U.S. for 2026 and recognized among the nation’s best many times over. Known for its powdery quartz sand and Gulf waters, it is one of the reasons living here is so special. Siesta Key Village is close by for restaurants, bars, live music and boutiques. Sarasota is just beyond the North Bridge, with downtown waterfront dining, shopping, galleries, theaters, performing arts and cultural attractions close at hand. Whether you are looking for a full time Siesta Key waterfront home or a second home for family and friends, 5376 Shadow Lawn Drive offers true boating access, a private saltwater pool, substantial updates, flexible living space and an exceptional island location. This is the kind of home where every day can include the beach, the boat and dinner by the pool. That is a pretty wonderful way to live.

5376 Shadow Lawn Drive, Sarasota

1313 Dockside Place Unit 120, Sarasota
$1,090,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
RARE BOATER’S OPPORTUNITY! 45' BOAT SLIP with NEW 27,000-lb IMM/Quality Platinum Series boat lift on deep, sailboat water! Completely renovated waterfront townhouse-style residence with the slip directly behind the unit—a highly desirable and rarely available location. Ultimate Beach lifestyle with easy access to Siesta #1 Beach & Siesta Village, just a few minutes' walk away. Enjoy mornings on the beach, afternoons on the boat, and evenings sunsets & exploring the Village. With many restaurants, music & shops. Fully remodeled down to the block walls with new plumbing, electrical, HVAC and ductwork, drywall, raised ceilings, LED lighting, and beautiful wood-look porcelain tile throughout. Gourmet kitchen features custom cabinetry, GE Profile appliances, natural quartzite, and abundant storage. Both baths offer easy-entry showers, and the primary suite includes a walk-in closet with custom organization. Private one-car garage, additional parking, attic storage, and newly screened lanai for entertaining. Elevated to 11.5' floor level remained free of stormwater during the 2024 storms. The dock features new pilings, full-length finger pier, fresh water, 30-amp/120V service, remote-controlled lift with auto-stop, and approximately 7' of water depth. Protected harbor approximately 100 yards from the ICW and just 10 minutes to Sarasota Big Pass. HOA permits boats up to 45' feet. Complex is getting a look and remodel! See photos Beach. Boating. Village life. All from one exceptional Siesta Key location. Community is going through a major face lift!! Scope of renovations • Siding/Trim/Facia with Stain-paint • Railings • Stairs • Gutter/Downspouts • Lighting

1313 Dockside Place Unit 120, Sarasota

4050 Higel Avenue, Sarasota
$25,000,000
5 Beds ⋅ 7 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. To be complete in a few months. An unmatched luxury beach estate, this Gulf-front upcoming masterpiece offers sweeping ocean views and a private stretch of sand on Siesta Key. Designed and built by Pham Development, the iconic Mid-Century Modern residence is privately gated and designed to deliver resort-level living on one of Florida’s most coveted coastlines, with breathtaking views of the Gulf’s sparkling waters. Spanning 14,943 sq. ft. under roof, with 6,301 sq. ft. of air-conditioned interiors, the home features 5 bedrooms, 6 full baths, and 1 half bath. Engineered for longevity, it rests on a fortified foundation with a planned riprap seawall installation, complemented by a luxurious infinity pool and hot tub overlooking the gorgeous Gulf waters. Lifestyle amenities rival the finest resorts: a rooftop with spectacular ocean views and a full personal fitness center with a yoga studio. Entertainment spaces abound, with opportunities for a movie theater room, an ocean-view office, a gun and jewelry safe room, and an enclosed garage accommodating up to 16 cars. Paddle board and kayak access lead directly to the Gulf, with options for a beach volleyball or pickleball court. The grand primary suite features an expansive Gulf-facing terrace, his-and-hers walk-in closets, and spa-inspired baths, with stunning water views creating a serene coastal retreat. Multiple terraces, a Wolf-equipped outdoor kitchen, a chef’s kitchen, and a butler’s pantry add to the all-inclusive luxury lifestyle of this home. The chef’s kitchen will feature a 72-inch Sub-Zero refrigerator, Cove dishwasher, and Wolf range, coffee maker, and microwave. More than a residence, this estate is a legacy home crafted for generations, with an indoor-outdoor footprint tailored for both grand entertaining and intimate coastal living, all framed by extraordinary Gulf views. One or more photos have been virtually staged. Private showings are available upon request.

4050 Higel Avenue, Sarasota

6005 Midnight Pass Road Unit S6, Sarasota
$839,000
2 Beds ⋅ 2 Baths ⋅ Provintial Gardens SubDv. ⋅ 34242 Zip Code
Escape the winter blues with this turnkey furnished free-standing villa ready for IMMEDIATE occupancy with DEEDED SIESTA KEY BEACH and BAY access steps away in a non age restricted community. No logistical headaches having to furnish a property in order to occupy or rent it. This beautifully decorated and extensively updated, maintenance-free, open floor plan, villa can be your very own piece of paradise. Offering two spacious bedrooms and bathrooms, a flex (den) space, a full size washer/dryer, and your very own lush private patio oasis, all designed with comfort and style in mind. Added peace of mind comes from no flooding or storm damage sustained from recent storms. Some of the many updates include an extensive renovation to replace the old 1960s cast iron drain lines under the property’s slab with all-new PVC lines. Once completed, designer selected wood look tile flooring was added throughout the majority of the home. This intrusive, time-consuming, and costly project has already been completed, putting a new owner at ease regarding future concerns and major costs. The roof and A/C are new as of 2025, exterior painting will be completed by December. The primary bathroom has been completely updated, along with new hardscaping and landscaping. Handpicked light fixtures and ceiling fans have been installed, along with brand new solid core doors throughout the home to reduce noise from room to room. New coastal colors and tones have been added to the interior, along with all new appliances within the past two years. For accessibility 36 inch doorways and grab bars are present, as well as smart home features such as keyless electronic front door entry, nest thermostat, and ring door bell. The residence invites plenty of natural light into the home, with multiple windows and sliding glass doors enhancing the appeal of the split floor plan. The primary and expansive guest suite are located on opposite sides of the villa, providing ample space and privacy for all. The kitchen features an abundance of soft close cabinets, granite countertops, a large pantry, water filter system, and stainless steel appliances. Throughout the villa, you will find plenty of built-in storage closets, crown molding, as well as both a walk-in shower (primary) and a soaking tub (guest). Open your three sliding glass doors to create a seamless extension of your living space into your private tropical sanctuary, complete with an outdoor shower. The guest suite includes its own private outdoor space with a water fountain. When you are ready to venture out and enjoy your surroundings, there is an endless list of options to keep you busy. Enjoy your morning coffee while watching the sunrise/wildlife at the community’s bay front park with a new seawall. Here, you will find a kayak launch with two storage racks specifically for your use. Head out on the water kayaking/paddle boarding among dolphins and manatees. The community’s bay front park includes a day dock for residents’ use. Choose between relaxing on the beach with the sand between your toes or reading a book by the pool, with deeded access to the beach and one of the largest heated pools on Siesta Key via Aloha Kai across the street. Catch the free trolley to enjoy a casual lunch or a fine dining dinner. Owners can rent their property on a monthly basis with three weekly rentals permitted a year (outside of Jan-March) and can have one pet. The monthly HOA fee is $1,113. Come enjoy winter on Siesta Key!

6005 Midnight Pass Road Unit S6, Sarasota

5830 Midnight Pass Road Unit 8, Sarasota
$429,000
1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
BEACH LOVERS AND INVESTORS, THIS ONE IS ALL ABOUT THE LOCATION! Welcome to Unit 8 at Jamaica Royale on Siesta Key, where being close to the beach doesn't get much better! Just steps from the world-famous Siesta Key Beach, this is one of the closest villas to the sand, making it easy to spend your days enjoying the Gulf's turquoise waters. Even better, the pool is right off your back patio, putting two of the most sought-after vacation amenities just outside your door! This prime location is a major draw for renters looking for the ultimate beach getaway. Thoughtfully renovated and designed to maximize comfort and functionality, this studio features a fresh coastal theme, luxury vinyl plank flooring, quartz countertops, and soft-close cabinetry. The inviting interior includes a Murphy-style bed, comfortable leather sofa, and dining for four. Offered turnkey furnished, it's ready for you to enjoy or begin generating rental income. Weekly rentals are permitted, and owners have the flexibility to use the onsite rental company or choose their own rental management. Even better, owners may have up to two pets! Beyond your villa, Jamaica Royale welcomes you with beautifully maintained grounds, lush tropical landscaping, private deeded beach access, and three resort-style pools. A nearby stop for the Siesta Key trolley makes it easy to explore Siesta Key Village, with its charming boutiques, local restaurants, and lively entertainment. Whether you're searching for a personal beach escape, a vacation rental investment, or the best of both worlds, this is your opportunity to own a slice of paradise in a location that truly stands out!

5830 Midnight Pass Road Unit 8, Sarasota

6840 Midnight Pass Road, Sarasota
$699,900
2 Beds ⋅ 4 Baths ⋅ Midnight Sea SubDv. ⋅ 34242 Zip Code
Live the Siesta Key lifestyle just moments from the beach! This beautiful three-level townhome offers 2 spacious bedrooms, plus an additional room on the lower level, 2 full baths, 2 half baths, an oversized one-car garage, and two additional outdoor parking spaces. The extra lower-level room could be used as a third bedroom, study, home office, gym, media room, or private guest space. The main living level features hardwood flooring, abundant natural light, and a screened lanai directly off the living room - perfect for morning coffee, outdoor dining, or relaxing after a day at the beach. A second private lanai is located off the primary bedroom, creating a peaceful personal retreat. Recent improvements include a new roof (2024), new electrical panel (2024), HVAC (2024), tankless water heater (2024), washer and dryer (2025), all four new toilets (2025), updated flooring on the stairs and in both bedrooms, and a completely renovated lower level with an added shower. (2024). Popcorn ceilings have been removed throughout all three levels. Additional exterior improvements include new water lines (2026), new pavers (2026), new gutters, fresh exterior paint, and hurricane-impact sliding doors throughout, the entire house was repiped. Enjoy the community pool and deeded beach access located approximately 200 yards away. The townhome is also conveniently close to Siesta Key’s south beach area, Point of Rocks, 7-Eleven, restaurants, shops, grocery options, and bike and recreational rentals. Previously enjoyed by the owners as their own vacation retreat and also used as a rental property (during season this home can produce $9-11K, and off season months - $4-5K), this townhome offers wonderful flexibility. It could be an excellent primary residence, second home near the Gulf, or investment opportunity in one of Sarasota’s most desirable beach communities. Offered furnished, including beach equipment, for an easy transition into island living. Seller is offering up to $500 toward a one-year home warranty of the buyer’s choice at closing. Start enjoying Siesta Key!

6840 Midnight Pass Road, Sarasota

6550 Sabal Drive, Sarasota
$2,850,000
4 Beds ⋅ 5 Baths ⋅ Sabal Palms SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. PRE-CONSTRUCTION OPPORTUNITY – SIDE-BY-SIDE LUXURY DUPLEX ON SIESTA KEY An exceptional opportunity to acquire a proposed newly constructed side-by-side luxury duplex at 6550 Sabal Drive on Siesta Key with nightly rentals legally allowed. Designed in a modern West Indies coastal style, the concept features two completely private residences, each offering approximately 2,240 square feet of conditioned living space, four bedrooms, four-and-one-half bathrooms, a private elevator, covered parking for two vehicles, an individual rooftop terrace and a private pool with outdoor entertaining area. The proposed building includes ground-level covered parking and private entrances, two elevated living floors and two divided rooftop decks. Each residence is planned with an open-concept great room, designer kitchen, spacious primary suite, ensuite guest bedrooms, luxury bathrooms and expansive indoor-outdoor living areas. The elevated construction is intended to complement the coastal setting while providing private accommodations for owners, guests or vacation renters. The property contains approximately 8,960 square feet of land and is zoned RMF-1. The existing property is operated as a legal two-family residence and offers convenient access to Siesta Key Beach, nearby restaurants, shopping, boating and the south Siesta Key Village area. This offering is ideal for an investor, multigenerational family or buyer seeking to occupy one residence while using or renting the second residence. The proposed duplex may also provide an opportunity for separate ownership of the residences through an approved condominium structure, subject to legal and governmental review. The offering is for a pre-construction development concept. Renderings, floor plans, dimensions, square footage, finishes, pools, rooftop terraces and other features are conceptual and subject to change. Construction has not commenced. Final design, development rights, permitting, zoning compliance, pricing, completion schedule and specifications remain subject to Sarasota County approval, architectural and engineering review, contractor pricing and a mutually acceptable construction agreement.

6550 Sabal Drive, Sarasota

5860 Midnight Pass Road Unit 23, Sarasota
$839,900
2 Beds ⋅ 3 Baths ⋅ Gulf Haven SubDv. ⋅ 34242 Zip Code
RARELY AVAILABLE CONDO IN GULF HAVEN ON SIESTA KEY BEACH! This nicely updated 2-bedroom, 2.5-bath unit in the highly desirable Gulf Haven community won't be on the market for long. With limited availability in this intimate beachfront community, you have a special opportunity to be a part of the Siesta Key community. This unit offers comfortable coastal living with a practical layout and inviting spaces. With two bedrooms and two-and-a-half baths, there is plenty of room for owners and guests to relax and enjoy everything island living has to offer. Private beach access is one of the standout features of Gulf Haven, giving you the ability to enjoy the soft white sands and beautiful Gulf waters. After a day at the beach, take a refreshing dip in the inviting community pool. A covered carport that is connected to the unit provides convenient, protected parking—another valuable feature on Siesta Key. The location puts you close to the best of Siesta Key and Sarasota. Enjoy easy access to Siesta Key Village, local shops and restaurants, boating, and more. When you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering exceptional dining, shopping, arts, entertainment, and cultural attractions. Whether you're looking for a vacation home, seasonal retreat, investment property, or full-time residence, this rarely available Gulf Haven condo offers an exceptional way to enjoy the Sarasota Gulf Coast lifestyle. Updated interiors, private beach access, a community pool, covered parking, and a location close to it all make this a property worth seeing. Opportunities to own in Gulf Haven don't come along often—come experience the Siesta Key lifestyle for yourself.

5860 Midnight Pass Road Unit 23, Sarasota

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