Apartments for Rent in Sarasota 34242 - 121 homes

Remarks: Welcome to your slice of paradise on Siesta Key, where island charm, relaxation, and convenience come together for the perfect beach getaway. This beautifully maintained 4-bedroom, 3-bathroom home is designed for making memories with family and friends. Spend your days lounging by the private heated saltwater pool, fire up the grill for an evening BBQ, or explore the island on the two complimentary bikes provided for your stay. Inside, the bright and spacious open-concept living area is filled with natural light and offers plenty of room to gather after a day at the beach. The fully equipped kitchen flows seamlessly into the living and dining spaces, making it easy to cook, dine, and connect. Comfortable bedrooms and three full bathrooms provide plenty of space for everyone to spread out and unwind. The home's private backyard is your own tropical retreat. Whether you're enjoying your morning coffee poolside, taking an afternoon swim, or relaxing under the stars after dinner, you'll quickly settle into the laid-back Siesta Key lifestyle. One of the best parts of staying here is the location. Leave the car behind and walk or bike to the world-famous sands of Siesta Key Beach or spend the day exploring Siesta Key Village, where you'll find fantastic restaurants, live music, unique boutiques, and island nightlife. Get ready to start each morning with a short stroll to The Local Bean for fresh coffee before heading to the beach! Highlights: 4 Bedrooms | 3 Bathrooms Private heated saltwater pool Outdoor grill 2 complimentary bikes Fully equipped kitchen Walk or bike to Siesta Key Beach and village Perfect for families, couples, and group vacations Please Note: This home is available for stays of 30 nights or longer in accordance with local rental regulations. Monthly rental rates vary seasonally. Please contact us for current pricing and availability for your desired dates. Call or text Catherine to schedule a tour or inquire for pricing!

Listing is courtesy of: SANDRONI HOLDINGS REAL ESTATE LLC (407-509-2911)

Listing Agent: Catherine Mitchell (609-367-2392)

Remarks: Florida charm at it’s best in this turnkey furnished vacation home on Siesta Key. The home is a mid-century in the style of the Sarasota School of Architecture. The home is on 1/3 of an acre on the Grand Canal with a dock and kidney-shaped heated pool. The new hardwood flooring and new impact windows make this home bright and inviting with volume ceiling space. The living room and kitchen offer delightful sunset views. This house is great for entertaining with a dry bar and amazing sunset views for everyone to relax. The two front bedrooms have French doors that lead out to a front screened porch that has a Zen feel--perfect for meditation or relaxation. The grounds are filled with exotic indigenous plants and trees. Dockage will accommodate a small boat, 23ft or smaller, or jet skis. Great getaway on Siesta Key, minimum 30 days require. The off Season rate is $6500 per month and Prime season rate is $10,500 per month Dec thru April

Listing is courtesy of: JENNETTE PROPERTIES, INC. (941-359-3435)

Listing Agent: Toyia Youtzy (941-915-7926)

Remarks: LOCATION, LOCATION, LOCATION!!! Available for a short term rental this expansive, water front, turnkey furnished, four bedroom plus a den, three and a half bathroom, single family home on the water on South Siesta Key is open to rent. Through the entrance on the first floor you enter into the family room with views of the pool and intracoastal waterway. The first level has a bedroom with queen sized bed, walk in closet and en-suite bathroom with a stall shower and a spacious living room with flat screen television. Laundry room with utility sink on this level. Up the open staircase leads to the main living floor with an open plan kitchen, dining room, living room combination and the den/office. The kitchen has a large island, plenty of counter and cabinet space for cooking/preparing, stainless appliances, breakfast bar and a wine fridge. All of these rooms overlook the pool and the intracoastal waterway. The primary bedroom has a king sized bed, comfortable sitting area, a water view, walk in closet and an en-suite bathroom that features a large garden tub, separate shower and double sinks. All bathrooms have been updated, and the bed sizes in all the two second floor bedrooms are queen sized. The home has a heated pool and hot tub, dock to tie up a boat which leads to the intercoastal waterway. Two car garage is not available for a renter but there is plenty of driveway parking. The owner will consider one small dog with a $300 refundable pet fee. WIDE OPEN FOR JANUARY 2027. SINGLE FAMILY HOME SIESTA KEY SARASOTA FLORIDA SEASONAL RENTAL

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: C. Alison Hunter (941-587-5667)

Remarks: Gorgeous updated 2 BR, 2 Bath condo on a Canal Available Now Through December 31st or April 1, 2027 and beyond! Sailboat water, fishing pier, private beach access directly across the street. Beautifully furnished vacation home with water view from main bedroom, Livingroom and lanai. End unit so more light and larger kitchen space. Everything you will need for your beach vacation. Amenities include heated pool, hot tub, saunas, three BBQ grills, outdoor eating space at the Clubhouse, Clubhouse with lots of activities, fitness center, library, shuffleboard courts and boat slips upon availability for a monthly fee. Siesta Harbor is a 55+ community with the Shuttle stop right in front of our complex for trips to the Village, dining and entertainment. You deserve Paradise!

Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)

Listing Agent: Rosie Dipasquale (614-313-7962)

Remarks: $4,800/month for annual renters! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Schedule your private showing today.

Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)

Listing Agent: Emerson Robbins (941-404-0382)

Remarks: BEAUTIFUL WATERFRONT CONDO IN SIESTA HARBOR! CANAL VIEWS • BEACH ACCESS • BOAT SLIPS ON SITE REASONABLY PRICE, CHECK AVAILABILITY. Condo available through January 15, 2027 or April 2027! Step into coastal luxury in this private, beautifully furnished corner end-unit in the highly sought-after Dolphin Building of Siesta Harbor. Enjoy gorgeous water views of the canal from your enclosed hurricane glass lanai, and walk just across the street to direct beach access. Spacious 2 Bedroom / 2 Full Bath layout, fully remodeled, Turn-key furnished with coastal décor and upscale appointments. Canal-front views from a bright, airy, light-filled space. Gourmet kitchen with granite countertops and rare extended layout! Modern upgrades throughout: frosted glass panel doors, accent walls, updated baths, Tile flooring throughout with a clean, coastal feel and High-impact windows and hurricane glass-enclosed lanai. Resort-style heated pool and spa along the wide canal. Active 55+ community with Clubhouse, fitness room, saunas, outdoor spa plus a fishing pier on the Intracoastal Waterway. Walkable to shops, restaurants, and iconic Siesta Key Beach and Siesta Key mini-donuts! Easy access on and off the key, SCAT stop and trolley just outside your door. Whether you're looking for a peaceful retreat or an active community lifestyle, this impeccably maintained, move-in-ready condo has it all. Elevate your living experience in one of Sarasota’s most desirable waterfront communities — your dream home awaits!

Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)

Listing Agent: Rosie Dipasquale (614-313-7962)

Remarks: Available for the 2027 Season or Two Week Rental. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis with a gorgeous view of the heated pool and ICW. Rental is turnkey furnished, decorated for immediate enjoyment with all of the amenities you will need for a relaxing vacation. The stunningly renovated interior features hurricane-rated windows, a modern quartz kitchen, vinyl plank wood floors and a stunning bathroom accented in gold. The open-concept living and dining area is filled with natural light, creating a bright and welcoming space ideal for relaxing or entertaining. Included is a washer and dryer, plenty of extra storage space directly across the hall and additional large washers and dryers located on each floor for larger items. Perfect for couples and extended stays, this retreat combines modern coastal finishes, large windows, and resort-style amenities just minutes from world-famous Siesta Key Beach and Siesta Key Village. For boating enthusiasts, you’ll find a beautiful marina with boat slips, as available, through the association as well as kayak storage. Two-week minimum renters enjoy an exceptional collection of amenities, including: *A large marina *Gulf access (no fixed bridges) *Heated swimming pool and shallow wading pool *Three tennis courts *Fully equipped fitness center with new showers and saunas *Clubhouse with social spaces and large kitchen •Outdoor BBQ and kitchen prep area under a beautiful new awning *For boating enthusiasts, boat slips are available through the association plus an ample kayak storage area.

Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)

Listing Agent: Rosie Dipasquale (614-313-7962)

Remarks: Available April 1, 2027! Beautiful two bedroom, two bath spacious condo. Furnished lanai with view of the Harbor and the Intracoastal Waterway - rarely available! Fifty-five+ community. Easy walk to deeded beach access to Siesta Key, the Number One Beach in the Country! Heated Outdoor Pool and Spa, Saunas, Modern Clubhouse, Patio Seating Area on the canal and our own Siesta Harbor Fishing Pier. Boat slips available by applying to the office. The trolley stop is at the entrance of the complex. Walk to restaurants and bars, easy on and off the key! You Deserve Paradise!

Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)

Listing Agent: Judith Guzzi (914-490-9032)

Remarks: Siesta Key living just steps from the Gulf of Mexico at beautiful, tranquil Island Reef on the quiet end of the Island. Spacious 2 bedrooms, 2 baths, laundry in residence, carport, and guest parking. Tile flooring throughout the condo. Island Reef is a serene waterfront community, one of the few true Gulf to Bay properties, that offers many desirable amenities including: beach and boat docks (lifts allowed), two lit tennis courts, pickleball, 2 fitness rooms, kayak storage, library, billiards, game room, clubhouse, two heated swimming pools, on site manager and more. Pet friendly! Imagine rising each day to panoramic vistas of the Gulf of Mexico, and to view coastal wildlife and breathtaking sunsets. Stroll over to the Bayside to enjoy the refreshing breezes and magnificent sunrises. Tropical gardens add to the appeal of Island Reef. Your new social life awaits a perfect 3-5 minutes walk to a trio of Siesta’s Keys favorite restaurants (casual and waterfront fine dining) or enjoy a complimentary trolley to Siesta Village for dining, shopping, ice crèam, mini donuts, cute brunch spots, yoga, and dancing every night of the week! SEASONAL GULF SIDE PRICE SCHEDULE: Jan-March 2026-$7,900.00 Leased (Unavailable January-March & April 2027) May-December 2026 is available. May 1st through December 30th 2026 is still available at $4,000.00 monthly.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Erick Shumway (941-544-3718)

Remarks: Located on Siesta Key with just a 3 minute walk to Shell Beach, this 2-story home is available NOW & FURNISHED for an ANNUAL LEASE. The kitchen flows seamlessly with an OPEN LAYOUT into the expansive living and dining areas filled with NATURAL LIGHT from the large sliding glass doors opening to the SCREENED-IN LANAI. The POOL & HOT TUB/SPA, also screened-in, are framed by lush TROPICAL LANDSCAPING including lemon, avocado, banana and mango trees! The COVERED PATIO space is ideal for sunset dinners, quiet mornings, or year-round relaxation in the coastal breeze. A SUN SHADE SCREEN is installed as well for maximum outdoor comfort. Plus a fully equipped OUTDOOR KITCHEN - perfect for entertaining. Inside your kitchen, enjoy: >> Thermador Stainless Steel Appliances >> Bar Fridge >> Shiloh Cabinetry >> Quartz Countertops >> Kitchen Island >> Breakfast Bar >> A whole house WATER FILTRATION SYSTEM with ULTRAVIOLET LIGHT The spacious primary suite on the 1st floor offers: >> Dual Walk-In Closets >> Dual Vanities >> luxurious Jacuzzi Tub >> Walk-In Shower 2 bedrooms share the 2nd floor. This home is concrete block construction on the first floor and a framed second floor with durable synthetic siding. It has IMPACT WINDOWS AND DOORS plus is equipped with a WHOLE HOUSE GENERATOR. There is a 2 CAR GARAGE plus a LAUNDRY with Washer & Dryer included. >> Siesta Key Village shopping and restaurants are a few minutes drive or bike ride >> 3 minute walk to Shell Beach >> Near the North Bridge with direct access to Publix, CVS, Barnes & Nobles, and more! >> 10-15 minutes drive from Mid Town & Downtown Sarasota SCHOOL DISTRICT: Phillippi Shores Elementary, Brookside Middle School, & Sarasota High School

Listing is courtesy of: KEYRENTER SARASOTA PROPERTY MANAGEMENT (561-889-2308)

Listing Agent: Benjamin Schwab (561-889-2308)

Remarks: Welcome to your dream home at 5151 Oakmont Place, nestled in the heart of the stunning Siesta Key, Sarasota, FL. This charming 3-bedroom, 2-bathroom residence offers 1,953 square feet of modern living space, designed for both comfort and style. Step inside to discover a thoughtfully laid-out floor plan that seamlessly blends contemporary design with functionality. The kitchen is a chef's delight, featuring sleek granite countertops and stainless steel appliances, perfect for culinary adventures. The bathrooms boast contemporary vanities and matching granite countertops, adding a touch of elegance to your daily routine. Enjoy the Florida sunshine in your private outdoor space, ideal for relaxing or entertaining guests. The home is equipped with central heating and air conditioning, ensuring year-round comfort. The attached two-car garage not only provides ample storage but also includes a convenient workspace for your projects. This pet-friendly home, with conditions, is unfurnished, allowing you to personalize it to your taste. Located approximately 1.5 miles from one of the best beaches in the country, you'll have easy access to the vibrant Siesta Key Village and a short drive to downtown Sarasota. Whether you're looking for a serene retreat or a lively community, this centrally located gem offers the best of both worlds. Don't miss the opportunity to make this beautiful home yours! Tenant will be responsible for a monthly lawn fee of $200.00.

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Beth Harris (941-321-7148)

Remarks: DIRECT BEACH ACCESS! Beautifully located 1 bed/1 bath second-floor unit in the sought-after Aloha Kai community on Midnight Pass Rd, This fully furnished unit offers relaxing pool views and is move-in ready in this well-maintained beachside community. Available for 2 adults, no pets. Water and electricity included in rent. On-site parking available. Steps from the sand — perfect for tenants wanting a true island lifestyle. Won't last long — schedule your showing today!

Listing is courtesy of: ROELENS REALTY & PROPERTY MANA (239-887-7674)

Listing Agent: Koen Roelens (239-887-7674)

Remarks: Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee at LeLu Coffee Lounge. 4 bedrooms and 2.5 baths brings you back inside with a large open living room and kitchen with breakfast bar. The master suite on the main level with en-suite bathroom with access to the pool. Upstairs you have 3 additional bedrooms.

Listing is courtesy of: M&M PROPERTY MANAGEMENT GROUP (941-320-4287)

Listing Agent: Joe Meszaros (941-320-4287)

Remarks: Discover your sunlit retreat in the desirable waterfront community of Sea Village on Siesta Key! This ground-floor, 2-bedroom, 2-bathroom condo offers a bright and spacious living environment. The open kitchen is perfect for those who enjoy cooking, and the living area provides ample space for relaxation and entertaining. Each bedroom is a comfortable haven with custom closets for added convenience. Enjoy the ease of your own in-unit washer and dryer. Plus, your furry friends are welcome here! Amenities include two pools, grilling area, lush green spaces, and a fishing pier. Enjoy your morning coffee from the covered lanai with potential views of the bright turquoise water and occasional dolphin sightings. The vibrant North Village, with its unique boutiques, fantastic restaurants, and live music, is just a short bike ride or stroll away.

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: Newly remodeled unit with stainless steel appliances and granite counter tops. Beautiful Florida room with an amazing view. It also has a kayak that is available for any tenants to use.

Listing is courtesy of: CASEY REALTY CORPORATION (941-922-3391)

Listing Agent: Pamala Casey (941-922-3391)

Remarks: Discover this exceptional 2-bedroom, 2-bathroom condo, perfectly positioned for the ultimate Florida coastal escape. Step out onto your dual balconies—one on the side and one in the back—offering breathtaking, unobstructed views of the serene Intracoastal Waterway. Watch boats glide by, spot dolphins playing, and soak in stunning the stunning views from your own private vantage points. This rarely available rental includes a dedicated boat slip at no additional cost—perfect for bringing your boat or simply enjoying the waterfront lifestyle without extra fees. The community amenities elevate your stay even further: relax in the sparkling pool, grill in the outdoor kitchen, or take advantage of exclusive deeded beach access to Siesta Beach—consistently ranked among the world's best beaches for its famous powdery quartz sand that stays cool underfoot, crystal-clear Gulf waters, and laid-back vibe. Inside, the unit is beautifully fully furnished and thoughtfully decorated with original art from a talented local artist—turn-key comfort and coastal charm. Whether you're planning a relaxing summer getaway, a family vacation, or an extended stay, this waterfront retreat delivers tranquility, convenience, and unparalleled access to Siesta Key's iconic shores and vibrant village life. If you're ready to claim your own slice of waterfront paradise this summer (or beyond), contact us today to schedule your private tour—availability won't last long! SIESTA KEY, SARASOTA VACATION RENTALS, BEACH RENTALS IN SARASOTA, SIESTA BEACH.

Listing is courtesy of: JENNETTE PROPERTIES INC (941-953-6000)

Listing Agent: Teresa Ribaudo (941-376-4500)

Remarks: • UNFURNISHED • ANNUAL RENTAL ~ Rarely available in the exclusive Hamilton Club, this spacious 3-bedroom, 3.5-bath townhome offers over 4,000 square feet of space in one of Siesta Key's most desirable deep-water boating communities. A standout feature of this home is the expansive lower-level garage area, providing exceptional flexibility. In addition to the oversized two-car garage, there is a substantial bonus space that can be used as a home office, fitness room, game room, workshop, extensive storage, or for storing a small boat, kayaks, canoes, paddleboards, and other recreational equipment. For boating enthusiasts, this property includes a private boat slip that can accommodate a large boat. The Hamilton Club is an intimate, gated community of only 18 residences, offering deep-water dockage with sailboat water access, no fixed bridges to Sarasota Bay, and direct access to the Intracoastal Waterway and the Gulf of Mexico. Inside, soaring ceilings, generous room sizes, and an open floor plan create an inviting atmosphere. The main level features a welcoming foyer, spacious living and dining areas, a large eat-in island kitchen, a versatile bedroom or den with a full bath, a laundry room, pantry, and powder room. Sliding doors open to a screened lanai overlooking lush tropical landscaping, a tranquil lagoon with a fountain, and the community's heated pool. A spiral staircase provides convenient access to the lower level. Upstairs, a generous bonus room separates two private bedroom suites. The oversized primary suite features a large walk-in closet and an elegant en-suite bath with a soaking tub and separate shower. A second en-suite guest bedroom provides privacy and comfort for family or visitors. Residents enjoy a heated community pool, as well as access to tennis and pickleball courts. Located on the north end of Siesta Key, the home is just minutes from Shell Road Beach, Siesta Village, and the world-famous white sand beaches and turquoise waters of Siesta Beach. Downtown Sarasota's exceptional shopping, dining, entertainment, and cultural attractions are only a 10-minute drive away. Opportunities to lease a home in Hamilton Club are exceptionally rare. If you're looking for spacious living, private boating access, and the Siesta Key lifestyle, this remarkable annual rental is not to be missed.

Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)

Listing Agent: Tony Andrews (941-921-5999)

Remarks: Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass doors that lead to a massive private balcony spanning both the living room and the primary bedroom. Step outside to take in sweeping views of the Gulf—perfect for morning coffee, sunset watching, and even spotting dolphins while you do the dishes. This residence offers 2 bedrooms and 2 full bathrooms, along with generous storage throughout. Free community laundry is conveniently located just down the hallway, and the unit has recently been painted, giving it a fresh, clean feel. Residents of Siesta Towers enjoy extensive amenities including a secure building, large heated Gulf-front pool, private park area, club room with full kitchen, fishing pier, BBQ grills with dining pier, fish/tackle room, bike storage, and a library. Located on the north end of Siesta Key, you are just a short walk to Siesta Key Village with its lively restaurants, shops, and entertainment. World-famous Siesta Beach is also nearby. Off the island, you are only minutes from Sarasota where you can enjoy theaters, opera, Marie Selby Botanical Gardens, museums, and the marina. How many times in life do you get the chance to live right on the beach? Call today to schedule your showing. Note: This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details.

Listing is courtesy of: RENT SARASOTA (941-328-8999)

Listing Agent: Cody Smith (404-991-0209)

Remarks: Look no further than Siesta Key's "Island Reef" for your annual vacation getaway. The stunning Gulf to Bay location features the fourth-floor unit overlooking the intercostal waterway, just a short walk to the beach. The Siesta Key village and local dining are just a stroll away. The property has a beautiful community pool, tennis courts, shuffleboard, and more. The stylish decorum and nicely appointed finishes invite you to relax and unwind. TVs and internet for your convenience will help you not miss a beat. This property will not disappoint. Please call with any questions. $4,000.00 a month Starting May 1 2026. Unit is available for January, February, March at $8,000.00 per month plus sales tax. From April 2027 on the rent is $4,000.00 per month plus sales tax.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Erick Shumway (941-544-3718)

Remarks: Leased 2027 season! Available 7/1/2026-12/31/2026. Direct beach front condo on Siesta Key beach. This unit has it all for that Florida vacation. 2 bedroom, 2 baths, located on the 2nd floor with private lanai. Living room and dining area face the Gulf of Mexico which allows for beautiful sunsets. The condo is tastefully decorated with wood and tile floors. Cool off in the pool located next to the unit, take a walk along the pristine sugary quartz sandy beach or take a swim in the turquoise waters of the Gulf. Just a short distance to shopping, dining and nightlife of Siesta Key Village.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Brenda Cozy (941-350-4889)