Siesta Key Homes with Pool Community Features

Siesta Key Homes with Pool Community Features

Welcome to Siesta Key, Florida – a slice of paradise nestled in Sarasota County known for its pristine beaches, vibrant culture, and luxurious living. Renowned for its powdery white sands and stunning sunsets, Siesta Key is not just a vacation destination; it’s a lifestyle. With a warm tropical climate year-round, residents enjoy an outdoor haven filled with recreational activities, from sailing and paddleboarding to beach volleyball and sunset strolls.

The real estate landscape in Siesta Key is as diverse as its residents, featuring an array of charming homes, many of which come equipped with private pools. Imagine unwinding in your own backyard oasis, surrounded by lush tropical landscaping, where you can soak up the sun or host unforgettable gatherings with family and friends. Homes with pool community features are abundant here, providing an ideal setting for those who cherish a luxurious lifestyle and the joy of outdoor living.

In addition to its stunning properties, Siesta Key boasts a vibrant community atmosphere. Residents are treated to an array of delightful restaurants, boutique shops, and lively entertainment options, all while enjoying the laid-back vibe that this coastal gem offers. The local community is welcoming and inclusive, making it easy to forge friendships and create lasting memories.

Whether you’re seeking a second home, a primary residence, or a rental investment, Siesta Key promises a unique blend of luxury, leisure, and natural beauty. Discover your dream home in this tropical paradise, where every day feels like a vacation!

Newest Siesta Key Homes with Pool Community Features

5760 Midnight Pass Road Unit 109, Sarasota
$1,289,000
3 Beds ⋅ 2 Baths ⋅ Gulf N Bay SubDv. ⋅ 34242 Zip Code
Rarely available and highly sought after, this beautifully renovated 3-bedroom, 2-bath residence is one of only a handful of lobby-level condominiums within Gulf & Bay Club. Perfectly positioned to capture expansive water views, the home offers breathtaking vistas from nearly every room, overlooking lush manicured grounds, serene lakes, and beautiful Gulf views stretching toward the horizon. The ever-changing backdrop of water, tropical landscaping, and coastal skies creates a sense of tranquility that is uniquely Gulf & Bay. A comprehensive floor-to-ceiling renovation has transformed the residence into a sophisticated coastal retreat. The living area was thoughtfully expanded to maximize both space and scenery, creating an open, light-filled environment where the spectacular views remain the focal point. With no elevator required and convenient access to the beach, pools, and community amenities, this coveted ground-floor location offers a level of accessibility and ease rarely found on Siesta Key. Lovingly maintained by its owners and never rented, the residence reflects pride of ownership throughout. Behind the beautiful finishes lies an extensive list of meaningful improvements, including impact-resistant windows and doors, a new HVAC system, luxury vinyl plank flooring, custom shades, and newer appliances, including a washer, dryer, garbage disposal, and a beverage/wine cooler at the dining area's dry bar, the perfect spot to prepare sunset cocktails and appetizers before heading out to enjoy another beautiful evening on Siesta Key. Offered turnkey furnished, this condo is ready to be enjoyed from day one. Brand-new La-Z-Boy furnishings enhance the living room, while carefully selected Pottery Barn pieces create a bright, serene atmosphere in the primary suite. The third bedroom features custom built-in cabinetry and provides office space including a full-size bed for guests. The spacious second guest bedroom comfortably accommodates two queen-size beds and includes built-in storage designed to maximize both function and comfort. Gulf & Bay Club offers a true resort-style experience set along 800 feet of private beachfront on world-famous Siesta Key Beach. Residents enjoy a beautifully maintained, gated community with on-site maintenance and an exceptional array of amenities, including three heated swimming pools, tennis and pickleball courts, fitness facilities, saunas, two clubhouses, beach chair service, and recently updated landscaping, fencing, beach enhancements, electric charging stations and grilling areas. Surrounded by tropical landscaping, scenic lakes, fountains, and winding pathways, Gulf & Bay delivers the atmosphere of a luxury coastal resort while offering the comfort and convenience of home. Location is key here, so close to shopping, dining, downtown Sarasota, the airport, and so much more! Need to head to Siesta Key Village for some fun? Hop on the free trolley; your possibilities are endless! Whether you're seeking a full-time residence or a seasonal escape, this exceptional property offers a rare combination of panoramic water views, extensive upgrades, turnkey convenience, and an unmatched Siesta Key lifestyle.

5760 Midnight Pass Road Unit 109, Sarasota
3936 Hamilton Club Circle Unit 6, Sarasota
$1,400,000
3 Beds ⋅ 4 Baths ⋅ Hamilton Club SubDv. ⋅ 34242 Zip Code
Siesta Key,exclusive gated community of only 18 homes with deep water marina,pool, and tennis court all within a private, lush, tropical paradise . Walking paths around a central lagoon , as well as a beautifully maintained boardwalk of Ipe wood bordered with mangroves , are among the things that make Hamilton Club so very special . Inspired by the architecture of Bermuda with its close ties to 17th Century Great Britian is recognized by its striking pastel colored walls and "welcoming arms"staircases . Very close to the Village and Crescent Beach yet equally convenient to Downtown Sarasota. This sophisticated townhome has been renovated with fine finishes , wood and stone are incorporated in a wonderfully artistic way. Soaring ceilings and a Southern exposure provide amazing ,cheerful lighting . Fabulous center island in a truly stunning kitchen with expansive counter space, premium appliances and elegant custom cabinetry .Large walk in pantry .

3936 Hamilton Club Circle Unit 6, Sarasota
5880 Midnight Pass Road Unit 706, Sarasota
$1,250,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
Experience ultimate coastal luxury at Casarina, ideally situated directly on the quartz-white sands of award-winning Crescent Beach. Welcome to Unit 706, a phenomenal 7th-floor residence offering wonderful elevated sightlines, a recently and tastefully remodeled interior, and the quintessential Siesta Key beachfront lifestyle. This thoughtfully maintained building provides exceptional resort-style amenities, including a heated beachfront swimming pool, soothing hot spring spa, clubhouse, fitness room, tennis courts, and private beach access. Boasting a perfect mid-Key location, you are just moments away from local island dining, boutiques, and convenient mainland access via the Stickney Point Bridge. Don’t miss this premier island opportunity.

5880 Midnight Pass Road Unit 706, Sarasota
6157 Midnight Pass Road Unit E24, Sarasota
$474,000
1 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Elevated living awaits in this beautifully appointed 4th-floor condo, located just minutes from the quartz sands of Siesta Key Beach. This turn-key residence offers a seamless blend of relaxed Florida style and incredible investment potential. The bright, airy interior is flooded with natural light, leading out to an east-facing screened balcony that overlooks lush, tropical landscaping. This condo features durable ceramic tile flooring throughout the main living areas, a well-equipped kitchen with stainless steel appliances, and a generous walk-in pantry. Storage is effortless thanks to a separate large closet designed to house all your beach and pool gear. Recent mechanical updates, including a brand-new water heater and a newer A/C system, for greater peace of mind. Positioned as a premier vacation destination, this property allows for weekly rentals, offering a fantastic opportunity to offset ownership costs with gross rental income ranging from $30,000 to $40,000 annually. Residents enjoy access to a resort-style community pool, tennis courts, a social room, and a fishing pier. The unit includes one assigned covered parking space along with ample guest parking. Whether you are looking for a personal getaway or a high-performing rental, this condo delivers the ultimate coastal lifestyle.

6157 Midnight Pass Road Unit E24, Sarasota
8773 Midnight Pass Road Unit 302G, Sarasota
$500,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
WELCOME TO PARADISE AT ISLAND REEF! This beautiful condo at 8773 Midnight Pass Road, Unit 302-G, is your opportunity to experience the ultimate Siesta Key lifestyle! Located in the desirable Island Reef community, this incredible Gulf-to-Bay property offers the perfect combination of island charm, relaxation, and resort-style living. Enjoy an amazing selection of community amenities, including two heated swimming pools, private beach access, tennis and pickleball courts, a fitness center, clubhouse, game room, library, shuffleboard, boat docks, fishing pier, kayak launch, and grilling areas! There's always something to enjoy, whether you're soaking up the Florida sunshine, getting out on the water, staying active, or simply relaxing with friends and neighbors. And the location? Absolutely fantastic! Just moments from beautiful beaches, wonderful restaurants, shopping, parks, and everything that makes Siesta Key one of Florida's most desirable destinations. Whether you're searching for your forever home, a seasonal escape, or your own tropical getaway, this is an opportunity to make those Florida dreams come true. At Island Reef, every day feels like a vacation! Come see why you'll want to call this incredible community HOME!

8773 Midnight Pass Road Unit 302G, Sarasota
1300 N Portofino Drive Unit 102, Sarasota
$449,995
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
THE SIESTA KEY LIFESTYLE, ALL IN ONE EXCEPTIONAL WATERFRONT COMMUNITY! Imagine starting your day with coffee overlooking a picturesque harbor, spending the afternoon with your toes in Siesta Key’s powdery white sand, and gathering with friends for sunset cocktails as another spectacular Florida day draws to a close. Welcome to Siesta Harbor Condominiums Association, a vibrant 55+ community where boating, beach days, and an inviting social scene come together in one extraordinary island setting. DIRECT WATERFRONT LIVING! Perfectly positioned on the ground floor, this beautifully updated, fully furnished 2-bedroom, 2-bath residence feels more like a private coastal home than a condo. Forget elevators and stairs - simply walk through your front door with groceries or beach bags and you’re home! Inside, a bright, breezy interior features attractive tile floors throughout and an open layout designed for easy entertaining. The remodeled kitchen is a showpiece, with gorgeous granite countertops, crisp white cabinetry, stainless steel appliances, a stylish glass backsplash, a generous breakfast bar opening to the living room, and the everyday luxury of a KITCHEN PANTRY—all with gorgeous views of the harbor! The living room flows into a spectacular glass-enclosed lanai, where walls of impact-resistant glass sliders frame intimate views of the harbor, lush tropical grounds, and boats gently resting along the waterway just beyond your windows. Imagine lingering here with a good book, watching the boats drift by, or savoring an evening cocktail in your own waterfront retreat. Two welcoming bedrooms include a flexible guest room with a Murphy bed, ideal for visitors or a home office. Updated bathrooms include a bidet toilet in the primary suite. Impact glass, tasteful furnishings, a private LOCKED STORAGE CAGE just down the hall, and on-site laundry and covered parking are welcome perks. Beyond your front door, the Florida lifestyle unfolds! Boaters will love the harbor's DIRECT INTRACOASTAL WATERWAY ACCESS WITH NO BRIDGES, situated just north of the South Bridge no-wake zone for convenient cruises south toward Venice. Imagine stepping aboard your boat just outside your home and setting off for a day on the water (slips subject to availability). Beach lovers will treasure DEEDED BEACH ACCESS directly across the street at Crescent Arms, opening the door to Siesta Key’s world-famous white quartz sand and sparkling Gulf waters. Spend sun-drenched afternoons by the community pool, relax in the hot tub, or enjoy the clubhouse, fitness center, library, billiards, and lively social activities. One of Siesta Harbor’s most cherished traditions is sunset happy hour on the waterfront sunset deck, where neighbors gather to toast another beautiful evening in paradise. Tucked into a peaceful waterfront setting, Siesta Harbor is just moments from South Siesta Key Village, with its grocery store, restaurants, bars, and charming boutiques. The nearby South Bridge makes mainland Sarasota wonderfully accessible, while the Breeze transit stops right in front of the clubhouse for a convenient way to explore the island. Whether your perfect day means cruising the Intracoastal, strolling the beach, sharing sunset cocktails, or simply relaxing beside the water, this is more than a condominium—it’s your invitation to live the SIESTA KEY LIFESTYLE you’ve always imagined! WHERE ELSE can you enjoy waterfront living and resort-style amenities under $500K on Siesta Key?

1300 N Portofino Drive Unit 102, Sarasota
6287 Midnight Pass Road Unit 106, Sarasota
$630,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
PRICED $30,000 LESS THAN LAST APPRAISAL REPORT (May 2026). Enjoy the best of the Siesta Key lifestyle at Excelsior Beach to Bay! This beautifully appointed 2-bedroom, 2-bath condominium features new plank tile flooring throughout the main living areas, with traditional tile flooring in both bathrooms. Hurricane-impact windows provide additional piece of mind. Residents enjoy deeded access to world-famous Siesta Key Beach, along with beautifully maintained tropical grounds and an impressive array of resort-style amenities. Relax by either of the two community pools, stay active on the tennis and pickleball courts, or take advantage of the fitness center, shuffleboard and outdoor grilling stations. Additional amenities include a community room, library and convenient on-site management. Each building offers assigned covered parking with ample additional parking for guests. An additional storage unity provides convenient space for beach chairs, bicycles, and all you beach essentials. Whether you're looking for a full time residence, a seasonal getaway, or an investment opportunity, Excelsior offers exceptional flexibility. Ideally located near Siesta Key's beautiful beaches, popular restaurants, shopping and entertainment, this is an opportunity to enjoy the very best of coastal Florida living!

6287 Midnight Pass Road Unit 106, Sarasota
1200 Cove Ii Place Unit 832, Sarasota
$549,900
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Turnkey 2BR/1.5BA Condo with Stunning Water Views – Steps from Crescent & Siesta Beaches! Welcome to your slice of paradise! This beautifully maintained 2-bedroom, 1.5-bath condo sits on the 3rd floor, directly across from the sugar sands of Crescent Beach and just a short stroll to world-famous Siesta Beach. Enjoy breathtaking views overlooking the marina and Intracoastal Waterway from your private balcony—perfect for morning coffee or sunset cocktails. Located in the highly sought-after Midnight Cove II, this community offers a vibrant coastal lifestyle with low maintenance fees that include Cable TV and Fiber Internet. No special assessments or surprises here as the community maintains fully funded reserves and passed the milestone inspection without missing a beat. Whether you're lounging at the heated pool, hitting the tennis, pickleball, or basketball courts, or simply soaking up the community vibe, there's something for everyone here. Offered turnkey furnished and priced to sell, this is a rare opportunity to own in one of the area's most desirable waterfront communities. Don't miss your chance to live the beach life or invest in a prime rental property!

1200 Cove Ii Place Unit 832, Sarasota
6415 Midnight Pass Road Unit P10, Sarasota
$850,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Experience coastal living at its finest in this beautifully renovated top-floor corner residences featuring 2 bedrooms and 2 bathrooms at The Anchorage on Siesta Key. Enjoy sweeping views of the Intracoastal Waterway, the pristine sands of Siesta Key Beach, and the beautiful Gulf of Mexico. Multiple balconies provide inviting spaces to take in the incredible surroundings, while generous storage, impact windows, a new water heater (2026) and A/C (2022) bring additional value and functionality to the residence. The primary suite opens to a private balcony where you can admire the sparkling Gulf by day and spectacular beach sunsets in the evening. The thoughtfully designed kitchen features stainless steel appliances and opens seamlessly to the dining and living areas, creating a welcoming space to relax or entertain while enjoying the beautiful surroundings. The split-bedroom floor plan places the two bedrooms on opposite sides of the main living space, providing added privacy for owners and guests. The living room balcony showcases the Intracoastal Waterway and Sarasota skyline, while the second bedroom offers its own peaceful waterfront outlook. The Anchorage is a gated community featuring deeded beach access, pickleball courts, a community pool, clubhouse, and boat slips. This residence also includes an under-building parking space and a private storage unit. Whether you're seeking a serene coastal retreat, a vacation getaway, or a special place to enjoy the Siesta Key lifestyle, this condo offers an exceptional opportunity to experience beautiful water views, breathtaking sunsets, and the best of island living. This condo is being offered furnished.

6415 Midnight Pass Road Unit P10, Sarasota
9203 Midnight Pass Road Unit 2, Sarasota
$1,895,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
SIESTA KEY WATERFRONT LIVING WITH BRAND-NEW PRIVATE DOCK, 16,000-LB BOAT LIFT, AND INTRACOASTAL WATERWAY VIEWS! Discover the ultimate coastal lifestyle at 9203 Midnight Pass Road, a beautifully renovated three-bedroom, two-and-a-half-bath waterfront residence ideally situated on the peaceful southern end of Siesta Key, just a short walk from Turtle Beach. Combining stylish interiors, exceptional boating amenities, and an unbeatable island location, this inviting retreat offers the perfect blend of comfort, convenience, and waterfront living. Thoughtfully updated throughout, the residence features a beautifully remodeled kitchen with contemporary finishes, renovated bathrooms, and comfortable living spaces designed for both everyday enjoyment and effortless entertaining. Two enclosed lanais provide an additional 356 square feet of versatile space, creating inviting areas to relax, entertain, or simply take in the tranquil Intracoastal Waterway views. For boating enthusiasts, this property truly shines. A brand-new private deep-water dock and newly installed 16,000-pound boat lift offer outstanding convenience and direct access to the Intracoastal Waterway and Sarasota's spectacular boating destinations. Whether spending the day fishing, cruising Sarasota Bay, or exploring the Gulf waters, the boating lifestyle is right outside your door. With these substantial waterfront improvements already completed, you can begin enjoying the freedom of waterfront living from day one. Additional highlights include a waterfront community swimming pool, convenient ground-level lanai access, and a pet-friendly community. With a three-month minimum rental period, this residence offers flexibility for year-round living, a seasonal Siesta Key getaway, or potential rental income. Most furnishings are also available separately, offering an opportunity for a convenient transition to island living. Ideally positioned near Turtle Beach, residents can enjoy beautiful Gulf sunsets, beachcombing, and leisurely shoreline strolls, while nearby waterfront restaurants, shopping, and the vibrant attractions of Siesta Key Village complete the coastal experience. Whether you're searching for a Siesta Key waterfront home, a boating retreat, or a seasonal Florida escape, 9203 Midnight Pass Road delivers an exceptional opportunity to enjoy the very best of waterfront living on Siesta Key.

9203 Midnight Pass Road Unit 2, Sarasota
6018 W Peppertree Way Unit 231B C, Sarasota
$1,124,900
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Just steps from the world-renowned Siesta Key Beach, Peppertree Bay offers the ultimate coastal lifestyle. Ideally positioned between the Gulf of Mexico and Sarasota Bay, this sought-after community features private, deeded beach access, beautiful waterfront surroundings, and resort-style amenities. It’s island living at its best! This beautifully positioned second-floor residence offers unobstructed Gulf views. The newly renovated lanai is a true highlight, featuring floor-to-ceiling windows that bring the breathtaking water views indoors, along with motorized blinds for effortless comfort and convenience. It’s the perfect place to enjoy morning coffee, spectacular sunsets, and the relaxed coastal lifestyle. A particularly desirable feature is the private garage with additional storage, a rare find among Siesta Key condominiums. With room for your vehicle, beach gear, bicycles, and more, you’ll appreciate the added convenience of having your own dedicated space. Two parking spaces add even more value. Offered turnkey furnished, the two-bedroom residence is ready to enjoy as a personal beach retreat or income-producing investment. The guest bedroom includes a Murphy bed for additional sleeping accommodations, making it easy to welcome family and friends. Peppertree Bay offers an impressive collection of resort-style amenities, including a heated swimming pool, fitness center, clubhouse, tennis and pickleball courts, all just a short walk from the residence. For added flexibility, the community allows rentals up to four times a year, with a one-month minimum, making this an appealing opportunity for those seeking a personal getaway with rental income potential. Whether you’re looking for a full-time coastal residence, a seasonal escape, or an investment opportunity, this Peppertree Bay property offers the beach, amenities, privacy, and convenience that make Siesta Key so special.

6018 W Peppertree Way Unit 231B C, Sarasota
9000 Blind Pass Road Unit B307, Sarasota
$895,000
2 Beds ⋅ 2 Baths ⋅ Fishermans Cove SubDv. ⋅ 34242 Zip Code
Come and see why Fisherman’s Cove is one of the most highly desirable communities on Siesta Key! This is one of the only complexes in which direct beachfront living also offers the boating lifestyle right out the back door! Discover an exceptional opportunity to own a top-floor 2-bedroom, 2-bath condominium offering 1090 square feet of coastal living, complete with an enclosed lanai showcasing breathtaking direct Gulf views and spectacular sunsets. One of the residence’s stunning features are new impact resistant glass sliders with in the lanai, an upgrade that beautifully captures the panoramic water views while allowing abundant natural light to fill the living space. Inside, the residence features attractive laminate flooring with sound-buffered installation throughout, light and bright colors and a spacious walk-in closet with a washer and dryer- very rare for a condominium. Offered turnkey furnished, this condominium is ready to enjoy as a full-time residence, private beach retreat, or investment property as WEEKLY RENTALS ARE ALLOWED! Newer HVAC and water heater are also a huge bonus. Beyond its incredible beachfront setting, Fisherman’s Cove offers a unique combination of Gulf-front living and boating convenience, featuring direct Gulf frontage and access to the Intracoastal Waterway. Residents enjoy approximately 900 feet of beautiful sandy beach, gated access, a heated community pool, kayak storage and dock, fishing from the community docks, and 40 boat slips available to owners and renters at no additional charge. Additional conveniences include elevator access, assigned parking, ample guest parking, storage, on-site management and rental office, and gas grilling areas along the picturesque lagoon. Experience the best of Siesta Key living with breathtaking Gulf sunsets, private beachfront access, exceptional boating amenities, and a welcoming waterfront community. An outstanding opportunity to own your very own piece of paradise!

9000 Blind Pass Road Unit B307, Sarasota
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