Location: Sarasota, 34242
Do Not Show Listings
9393 MIDNIGHT PASS RD #806, SARASOTA, FL 34242
$2,79526 Days on yellowkey MLS ID: A4695138
REDUCED by $200 (6.7%) on 07/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1975Community: Pointe On Midnight PassCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
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. Annual lease now avail $2195/mo. Off Season Rental April - December $2195 month and Seasonal December -March $3600 month 3 month minimum rental required!
Listing is courtesy of: CASEY REALTY CORPORATION (941-922-3391)
Listing Agent: Pamala Casey (941-922-3391)
1355 S PORTOFINO DR #103, SARASOTA, FL 34242
$12,00062 Days on yellowkey MLS ID: A4693257
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1389 Built: 1975Community: Siesta Harbor IiiCondo
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
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)
734 BIRDSONG LN, SARASOTA, FL 34242
$6,90015 Days on yellowkey MLS ID: A4696907
REDUCED by $600 (8.0%) on 07/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1890 Built: 1972Community: Siestas Bayside Waterside SouthSpa: NoSingle Family
Remarks: Annual Luxury Rental – 3 Bedroom Pool Home on Siesta Key offers an Oversized Primary Bedroom with a ensuite bathroom, large walk in closest, seperate den/workout room looking over the heated pool. Two additional oversized Bedrooms one with a King bedroom set and the other with a Queen and two twins which sleeps 4 also with built in closets and smart tv's. Beautifully appointed and fully turnkey furnished, this exceptional residence features an open and inviting floor plan with designer finishes, spacious living areas, and a fully equipped kitchen with stainless steel appliances. Step outside to your own private tropical paradise, complete with a sparkling pool, outdoor covered dinnig and a Grill area, lush landscaping, and a beautifully maintained backyard designed for relaxing or entertaining. Whether you're enjoying your morning coffee by the pool or hosting friends for an evening under the stars, this outdoor space is truly spectacular. Additional features include a 2-car garage,outdoor shower, in-home laundry, ample storage,a second french door refrigerator with a cafe ice maker and everything needed for year-round living. Ideally located just minutes from Siesta Key's world-famous beaches, fine dining, shopping, marinas, and downtown Sarasota, this home offers the ultimate Florida lifestyle. Rental terms are negotiable furnished or unfurnished. Luxury at its best—this exceptional Siesta Key home offers the perfect opportunity to enjoy year-round island living in one of Florida's most desirable locations. A must see!
Listing is courtesy of: WILLIAM RAVEIS - FLORIDA LLC (941-867-3901)
Listing Agent: Bob Mcgrath (941-628-1069)
3954 HAMILTON CLUB CIR #14, SARASOTA, FL 34242
$5,5004 Days on yellowkey MLS ID: A4699460
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2798 Built: 1997Community: Hamilton Club Siesta KeyCondo
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)
726 BIRDSONG LN, SARASOTA, FL 34242
$5,52555 Days on yellowkey MLS ID: A4694343
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1822 Built: 1972Community: Siestas Bayside Waterside SouthSingle Family
Remarks: AVAILABLE after September 10, 2026! Enjoy your own slice of paradise on World Famous Siesta Key! This beautifully renovated turnkey 3-bedroom, 2-bath heated pool home is just a short distance from the #1-rated beaches and the charming shops and restaurants of Siesta Key Village. Whether you're here for million-dollar sunsets, endless watersports, the famous Sunday Drum Circle, or simply peaceful days spent relaxing by the pool, this home is the perfect place to settle in and enjoy it all. The home comfortably sleeps 6-8 guests, with a king bed in the primary bedroom, a queen bed in the second bedroom, and a twin bed with a pull-out trundle in the third. The full-sized chef’s kitchen overlooks the pool, while two separate gathering spaces provide plenty of room to relax, unwind, or entertain. Outside, the fabulous outdoor living space invites you to soak up the Florida sunshine in your own private retreat. 30-day minimum term only. Jan-April = $9,200, May-October = $5,525, November = $6,300, December = $7,350. 13% tourism tax added to all leases under 6 months. Just bring your toothbrush and sunscreen! SORRY, NOT AVAILABLE AS AN ANNUAL RENTAL. Currently booked through Sept 10 2026 and again from Dec 15, 2026-Mar 31, 2027.
Listing is courtesy of: TNG REAL ESTATE (941-773-9599)
Listing Agent: Scott Nold (941-773-9599)
4822 OCEAN BLVD #5F, SARASOTA, FL 34242
$3,300126 Days on yellowkey MLS ID: A4685737
0 Days Off yellowkey (back on 7/10/2026)
Bed: 2 Bath: 2.0 Gar: 9 Liv Area Sq Ft: 1435 Built: 1973Community: Siesta TowersSpa: NoCondo
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)
8770 MIDNIGHT PASS RD #402B, SARASOTA, FL 34242
$8,0001120 Days on yellowkey MLS ID: A4574241
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1286 Built: 1975Community: Island Reef ICondo
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)
8770 MIDNIGHT PASS RD #302B, SARASOTA, FL 34242
$4,0001120 Days on yellowkey MLS ID: A4573996
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-$7,700.00 Leased (Unavailable January-March & April 2026) May-December 2026 is available. May 1st through December 30th 2026 is still available at $4,000.00 monthly.
460 BEACH RD #A1, SARASOTA, FL 34242
$8,0002092 Days on yellowkey MLS ID: A4481650
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1363 Built: 1980 Tax: $9,551 (2021)Community: SpindriftCondo
Taxes:$9,551
Tax Year: 2021
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)
4660 OCEAN BLVD #G1, SARASOTA, FL 34242
$3,30074 Days on yellowkey MLS ID: A4692031
REDUCED by $100 (2.9%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971Community: Sea VillageCondo
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)
5456 AZURE WAY, SARASOTA, FL 34242
$6,19513 Days on yellowkey MLS ID: A4698734
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2476 Built: 1969Community: Siesta IslesSpa: NoSingle Family
Remarks: This is an unfurnished 3 bedroom, 3 bathroom home with a screened pool and Grand Canal waterfront in the Siesta Isles community on Siesta Key! This residence features a terracotta tile roof, a paver driveway, an oversized two-car garage, and a stone-accented exterior framed by mature tropical landscaping. Inside, the home offers an open, split-bedroom floor plan with vaulted and cathedral ceilings, and neutral tile flooring throughout. The entry foyer has a decorative tile inlay and a wood front door with glass sidelights. The eat-in kitchen features stone countertops, antique-white solid wood cabinetry, a tile backsplash, stainless steel appliances including a double-oven range, and a peninsula with a breakfast bar, with a double sink set beneath a window overlooking the lanai. The kitchen opens to the adjacent family room for a connected living and dining space. The great room is anchored by a floor-to-ceiling stone decorative fireplace and has sliding glass doors that open to the screened pool with the canal beyond. Near the entry is an additional living and dining space distinguished by a curved bank of windows. The master suite has a vaulted ceiling, a walk-in closet with custom built-in shelving, and a private bathroom with a dual-sink vanity and a walk-in tiled shower with a bench seat. There are two additional bedrooms, and a spare bathroom with a tub/shower combination. An oversized interior laundry room includes a utility sink and cabinet storage, and a washer and dryer are included. The oversized two-car garage offers built-in cabinet storage. Outdoor living centers on a screened lanai with a paver deck and an in-ground pool overlooking the Grand Canal, with a paver patio and stone gas fire pit alongside it. The point lot includes a 189-foot seawall, a dock, and an 8,000 lb boat lift, with deep boating water leading out to Roberts Bay and the Intracoastal Waterway. There is also a poolside full bathroom that is only accessible from the patio. Siesta Isles is a waterfront neighborhood built across man-made islands threaded by about four miles of deepwater canals, located in the center of Siesta Key just north of Siesta Beach. The home is close to Siesta Public Beach, to the shops and restaurants of Siesta Village, and is not far from downtown Sarasota. We score every application. If an application doesn't score high enough, the resident may be required to place the equivalent of two months' rent in a security deposit. This home is being leased by Sarasota Management & Leasing, however it will be managed by the owner.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING (941-377-8400)
Listing Agent: Todd Roughton (941-377-8400)
211 ISLAND CIR, SARASOTA, FL 34242
$14,000370 Days on yellowkey MLS ID: A4658382
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1452 Built: 1961Community: Sarasota BeachSingle Family
Remarks: AVAILABLE for 2026... Jan., Feb and April Fantastic pool home located .4 mile from Siesta Beach access! Enjoy this completely renovated 3 bedroom / 2bath pool home in Palm Island on Siesta Key. With comfort in mind, vacation memories are waiting to be made here! All furnishings, appliances and flooring are new and decorated in coastal colors. Enjoy a morning walk to the powdery sand beach less than a mile away or enjoy swimming in your own salt water heated pool. Siesta Key has made #1 Beach for many years! Siesta Village has lots of shops to browse and restaurants to explore! Please Note: Property Owner has installed an audio/video enabled doorbell on front door to monitor home security (audio/video access not available to guest). All bedrooms and living room are equipped with Smart TV's. This home may be available for shorter stays, please call for rates. Non-aggressive dog welcome with owners approval.
301 AVENIDA MADERA #B, SARASOTA, FL 34242
$12,60082 Days on yellowkey MLS ID: A4690443
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1970Spa: NoSingle Family
Remarks: Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright open floor plan with a relaxed coastal theme, a fully equipped kitchen featuring granite countertops, stainless steel appliances, and a Keurig coffee maker, plus a spacious dining area overlooking a peaceful canal. The home comfortably sleeps up to 6 guests with a queen-size sofa bed and an auto-inflatable queen EZ bed, while the primary suite includes a private full bathroom. Step outside to enjoy true Florida living—grill out, swim, sunbathe, or fish right from the canal, and don’t forget your furry companions as this property is extremely pet-friendly. The shared pool area (with Unit A) adds to the experience, while both units has private entrances with no shared interior walls, ensuring added privacy. For peace of mind, exterior security cameras are in place, and the unit is strictly smoke-free with no indoor smoking permitted. Whether you're walking, biking, or taking the trolley to Siesta Key Village, everything you need is within reach—making this an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle.
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Robert D. Bevington (412-671-3142)
301 AVENIDA MADERA #A, SARASOTA, FL 34242
$12,60082 Days on yellowkey MLS ID: A4690447
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1970Community: Siesta Manor Sec 1Spa: NoSingle Family
Remarks: If you’re searching for the perfect location for your next vacation, your search ends here! This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid surface countertops, stainless steel appliances, and a charming breakfast nook. The spacious primary suite offers a king-sized bed and a private en suite bathroom with a walk-in shower. A standout feature of this home is the private rooftop deck, complete with outdoor furniture, a grill, and umbrellas for shielding the sun- perfect for enjoying sunny afternoons or relaxing evenings while taking in stunning sunset views over Siesta Key Beach. During the day, enjoy the convenience of walking to the beach, local shops, and restaurants, or take a short drive over the bridge into Sarasota for even more dining, shopping, and entertainment options. This pet-friendly home is ideal for family gatherings, and for larger groups, Unit B can also be rented for additional space. The pool area is shared with the neighboring unit, while both units maintain privacy with separate entrances and no shared interior walls. The home is strictly smoke-free with no indoor smoking permitted. Enjoy your stay in this exceptional island retreat!
5253 AVENIDA DEL MARE, SARASOTA, FL 34242
$4,50025 Days on yellowkey MLS ID: A4697624
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1438 Built: 1950Community: Sarasota BeachSingle Family
Remarks: This is a short-term rental. Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key Beach and Siesta Key Village. This coastal-inspired home features 3 bedrooms, 2 baths, bright open living spaces, comfortable furnishings, and plenty of room for the family to enjoy. A fully equipped kitchen, inviting indoor-outdoor living areas capture the essence of Florida coastal living, whether you’re catching world-famous sunsets on the quartz sands of Siesta Beach or grilling in the private, lush backyard, this is your perfect Florida getaway.
1203 LYRIC LN, SARASOTA, FL 34242
$7,500384 Days on yellowkey MLS ID: A4656825
REDUCED by $2,000 (21.1%) on 06/05/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2605 Built: 1964Community: Acreage & UnrecSingle Family
Remarks: Coastal Luxury Rental – Steps from Siesta Key Beach & Turtle Beach/Midnight Pass ***Seasonal or Annual Lease Available | 2 Bed • 2 Bath • Detached Garage /Game room/Workspace • RV Pad w/ 50-Amp + Pump-Out. Live the ultimate Siesta Key lifestyle in this completely remodeled and newly furnished coastal retreat, ideally located just ½ mile from the #1 rated Siesta Key Beach.***This stunning 2-bedroom, 2-bath residence features a private detached garage that doubles as a game room, home office, or creative workspace, plus a dedicated RV pad with 50-amp electrical hookup and pump-out station — an extremely rare amenity this close to the beach. ** Property Highlights: **Fully renovated interior – like new **Professionally furnished – turnkey & move-in ready** Bright open floor plan with coastal-inspired design** Modern kitchen with updated appliances & finishes ** Detached garage / game room / workspace – rare bonus feature ** Private outdoor areas perfect for relaxing or entertaining. ** Prime Location:** ½ mile to Siesta Key Beach ** Minutes to Siesta Village restaurants, nightlife & boutiques ** Easy access to downtown Sarasota, marinas, boating & golf.***Lease Options: Fully Furnished > Seasonal or Annual lease available*** This is a rare opportunity to lease a fully remodeled, professionally furnished home with RV parking & hookups, located minutes from Siesta Key Beach — perfect for snowbirds, traveling executives, digital nomads, boaters, and RV enthusiasts.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Tracy Srodes (813-267-1312)
3919 ROBERTS POINT RD, SARASOTA, FL 34242
$7,99556 Days on yellowkey MLS ID: A4694087
REDUCED by $1,980 (19.8%) on 06/30/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2497 Built: 2016Community: Siesta Rev OfSpa: YesSingle Family
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)
5159 OAKMONT PL, SARASOTA, FL 34242
$10,00015 Days on yellowkey MLS ID: A4698222
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1953 Built: 1977Community: Siesta BeachSingle Family
Remarks: Experience the best of Siesta Key in this beautifully updated private pool home, Available January - March 2027 only. Beautiful resort-style living, completely renovated interiors, multiple living and dining areas, comfortably sleeps 8-10 at one of Florida's most sought-after beach destinations for the perfect coastal getaway. Inside, the open-concept layout creates an inviting central living space, with the living room opening to the dining area and updated kitchen. Luxury vinyl plank flooring, recessed lighting, modern fixtures, and contemporary ceiling fans create a clean coastal feel throughout. The fully equipped kitchen features stainless steel appliances, abundant cabinetry, generous counter space, and a breakfast bar with seating, making everything from morning coffee to family dinners effortless. Beyond the main living area, a separate family room with a fireplace and adjoining breakfast nook provide an additional space to relax, watch a movie, play games, or enjoy a quiet meal. The split-bedroom floor plan offers privacy for everyone, with spacious accommodations designed to comfortably host family and friends. The primary suite features sliding doors opening directly to the lanai, while an additional guest bedroom also enjoys direct access to the pool, allowing guests to step outside and enjoy the Florida sunshine with ease. The screened lanai is where this home truly shines. Multiple covered seating areas provide space to dine, lounge, or unwind in the shade, while the sparkling private pool is surrounded by lush tropical landscaping that creates an inviting sense of privacy. Whether you're spending the afternoon poolside, enjoying dinner outdoors, or relaxing after a day at Siesta Key Beach, this backyard is designed to be enjoyed from sunrise to sunset. Located just minutes from the powder-soft quartz sand of Siesta Key Beach, as well as the shopping, restaurants, and nightlife of Siesta Key Village, this exceptional monthly rental places you in the heart of one of Florida's most iconic beach destinations. SORRY NO PETS PERMITTED. ONE MONTH MINIMUM stay, 90 DAY Jan 1 - March 30 PREFERRED. All leases are subject to 13% tourism tax.
Listing is courtesy of: TNG PROPERTY MANAGEMENT (941-773-9599)
1700 COVE II PL #310, SARASOTA, FL 34242
$2,95019 Days on yellowkey MLS ID: A4697340
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979Community: Midnight Cove IiCondo
Remarks: Available 2950.00 Monthly - April 20th 2026 through December 31st 2026... Not Available 2027 Jan through April 15th 2027 Stunning Water Views & Deeded Beach Access | Siesta Key plus taxes and fees. Live your Dream on Siesta Key for the Summer... Welcome to your perfect beach getaway! This 2-bedroom, 1.5-bath condo in Midnight Cove II offers breathtaking water views from both the unit and the spacious patio, along with deeded access to the powdery whi te sands of world-famous Siesta Key Beach—just across the street. Enjoy bright, open living spaces with floor-to-ceiling pocket sliding doors that flood the home with natural light and provide seamless indoor-outdoor flow to the lanai. Located in a beautifully maintained resort-style community, amenities include: Heated pool Pickleball & tennis courts Fitness center Fishing piers Marina access On-site management Deeded beach access Perfectly situated near Siesta Key’s lively South Village, you're just steps from top restaurants, shopping, and entertainment Whether you're planning a relaxing vacation or an extended stay, this rental offers the comfort of home with resort-style amenities in one of the most sought-after locations on the Gulf Coast. Available for weekly rentals – book your stay in paradise today! Not Available 2027 Jan through April 15th 2027
4051 SHELL RD, SARASOTA, FL 34242
$6,50042 Days on yellowkey MLS ID: A4695400
0 Days Off yellowkey (back on 6/25/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3031 Built: 1985Community: SiestaSingle Family
Remarks: Rare Siesta Key annual rental and Gulf-front home with private beach access, pool, outdoor shower, 4 bedrooms, 4 bathrooms, oversized 2 car garage, circular driveway, and direct access to the Gulf of Mexico. Located on North Siesta Key, this architecturally distinctive waterfront home offers private beach frontage, spectacular sunsets, and views toward Big Pass, Lido Key, Downtown Sarasota, and the Ringling Bridge. Offered unfurnished, this approximately 3,031 square foot home is ready for you to make it your own. Soaring cathedral ceilings, bamboo flooring, floor-to-ceiling windows, abundant natural light, a dramatic freestanding fireplace, and multiple levels of living space create a home that feels both spacious and inviting. The kitchen features a gas range, breakfast bar seating, dining area, and opens to the main living spaces, while French doors lead to a spacious deck overlooking the outdoor living areas. The flexible floor plan includes a huge lower-level fourth bedroom with full bath, washer and dryer, and direct access to the patio and pool area. The upper level includes the primary suite and an additional bedroom, both with ensuite bathrooms, along with loft spaces that provide excellent flexibility for home offices, fitness areas, hobby spaces, reading retreats, or additional living areas. The primary suite features a private deck and elevated views toward the Gulf. Outside, enjoy the private pool, outdoor shower, multiple decks, beach access, and ample storage for paddleboards, kayaks, bicycles, fishing gear, and beach equipment. The oversized 2 car garage and circular driveway provide plenty of room for vehicles and guests. The North Siesta Key location offers convenient access on and off the island via the North Bridge, while Siesta Key Village, Downtown Sarasota, St. Armands Circle, waterfront dining, shopping, and Sarasota's cultural attractions are all nearby. Recent improvements include updated exterior siding, newer air conditioning system, and additional storm-related property improvements. Available for annual lease. Pets may be considered at owner's discretion.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Josie Cline (941-266-6661)
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