$2,300 per month
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
5631 Midnight Pass Rd Unit 1001, Sarasota, FL 34242
$2,900 per month
1215 S Portofino Dr, Siesta Key, FL 34242
AVAILABLE NOW! Enjoy the island living in this cute and cozy 2 bedroom, 2 bathroom condo with canal views! Nestled in the heart of Siesta Key, this 55+ Community has it all! The unit is newly painted and adorned with coastal flair, a king size bed in the master bedroom and a queen size in the guest bedroom, vinyl flooring and a screened in lanai. One of the best features of this unit is the water
$13,500 per month
577 Venice Ln, Sarasota, FL 34242
Experience luxury living in this 2021 custom pool home located in one of Siesta Key’s most desirable neighborhoods. Featuring four spacious bedrooms, 3.5 baths, and a dedicated office, this modern West Indies-inspired home offers an open floor plan with soaring ceilings, abundant natural light, and coastal design. The gourmet kitchen boasts quartz countertops, stainless appliances, a walk-in
Robert Ruiz WILLIAM RAVEIS REAL ESTATE
$2,495 per month
612 Canal Rd, Sarasota, FL 34242
ANNUAL RENTAL! Again, an annual rental (12 months) on Siesta Key -- Fantastic Location!!!! Immaculate & Adorable, Beachy ! This 2 bedroom 1 bath Beach Cottage- Walk to beach and the Village! The first person to see it will want it - it's that nice! BIG YARD - and mowing is included in the rent. Owner is looking for a long term Renter! CREDIT, BACK GROUND, EVICTION CHECK FOR ALL TENANTS - ALL MUST
Tony Andrews ANDREWS & ASSOCIATES REALTY
$3,500 per month
5740 Midnight Pass Rd Unit 207, Sarasota, FL 34242
Enjoy breathtaking Siesta Key sunsets from this beautifully appointed 2-bedroom, 2-bath condominium located in the highly sought-after Gulf & Bay Club. This 1,340 sq. ft. end-unit residence is turnkey furnished and move-in ready, offering the perfect blend of comfort and coastal charm. Extra side windows flood the space with natural light, while tranquil views of the meditation garden and treetop
Robert Bevington SHOWTIME REALTY
$5,995 per month
935 Contento St, Sarasota, FL 34242
Rare waterfront Siesta Key pool home available for annual rental! This beautifully-renovated 3/2/2 pool home in Siesta Isles is available for immediate occupancy. This impressive property offers 100 feet of waterfront along Siesta Key's Grand Canal. The gourmet kitchen features quartz counters, stainless steel appliances, built-in microwave/wall-oven combo, island cooktop with hood vent, and
Jennifer Herman MOUNT VERNON PROPERTY MGMT INC
$6,200 per month
1224 S View Dr, Sarasota, FL 34242
Stunning Renovated Home for Long-Term Rent in Siesta Cove. Discover your dream coastal lifestyle in this beautifully renovated single-family home located in the exclusive neighborhood of Siesta Cove, just steps away from the acclaimed Siesta Key Beach—voted the number one beach in the United States! This elegant residence boasts 3 spacious bedrooms and 2 luxurious bathrooms, offering a high
Beth Dilley ASCENDIA REAL ESTATE
$7,500 per month
306 Island Cir, Sarasota, FL 34242
Available now. Lovely pool home with canal water frontage located in Siesta Key's peaceful and secluded neighborhood of PalmIsland. Completely renovated with new kitchen, bathrooms, and floor coverings throughout this island retreat. Walk four blocks to the crystalsands of world famous Siesta Beach, and just a short walk to the Village. Beautiful backyard with spacious patio, heated swimming
Timothy Bloch QUEST PROPERTIES INC
$4,000 per month
4822 Ocean Blvd Unit 8B, Sarasota, FL 34242
Annual turnkey furnished Live on the GULF OF MEXICO, ON SIESTA KEY!!! Siesta Towers is a luxury 11 story, 65 unit condominium that is oceanfront Siesta Key with panoramic views of the Gulf of Mexico. This condo is a comfortably and stylishly furnished 2/2 with open floor plan and is flooded with natural light from double sliding glass doors that lead to your massive balcony. The balcony
Henry Rossi RENT SARASOTA
$5,400 per month
9 Sandy Cove Rd Unit 8A, Sarasota, FL 34242
Private Beach. 2/2/1 Car Garage. Rarest of Rare! Experience the Best of Florida Living in Your Very Own ParadiseWelcome to the ultimate beachfront escape! This one-story gem perfectly blends luxury, convenience, and breathtaking natural beauty. Whether you're a seasoned traveler looking for a private haven or someone searching for a peaceful retreat, this property has everything you could dream
Sandra LaFlamme EXP REALTY LLC
$3,750 per month
5911 Midnight Pass Rd Unit 504, Sarasota, FL 34242
Located in the gated Boca Siesta Condominium on Siesta Key, this beautifully maintained 5th floor fully furnished condo features 2 bedrooms and 2 bathrooms, and breathtaking views of Little Sarasota Bay and the Intracoastal waterway is now available as a long-term rental. Upon entering the condo, you are met with a bright, open, nicely furnished living and dining room area, with beautiful water
Chrissie Cummings JENNETTE PROPERTIES INC
$2,400 per month
4439 Ocean Blvd Unit 2A, Sarasota, FL 34242
Take a look at this beautifully decorated well priced 3 bed 2 bath home for rent in a prime location! This home is within walking distance to the beach, and several other restaurants and amenities. Call today for a showing, this won't last long! Can come furnished or unfurnished.
Dalton Hope REALTY ONE GROUP MVP
$2,800 per month
5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
BEAUTIFULLY UPDATED 4th Floor Condo is quiet. The 2-bedroom, 2-bathroom condo with coastal decour is turn-key furnished split- floor plan. Includes a washer and dryer. The gated community offers large pool and resident and guest parking. within the Harbor Towers Yacht & Racquet Club on Siesta Key, home to #1 beach in USA. Condo has spacious 1,056 sq ft layout with luxury vinyl plank flooring
Anna Williams SHOWTIME REALTY
$12,600 per month
301 Avenida Madera Unit B, Sarasota, FL 34242
Current Availability: 4/6/2025 This is THE location! Just steps to the Village cafe and the Hub Bar and Grille, and a short walk to the beach. Our 2 bedroom 2 bath beautifully updated property offers a coastal theme and open floor plan. A queen size sofa bed and an auto -inflatable queen size EZ Bed, makes this home comfortable to sleep 6 occupants. Granite countertops, stainless steel
Robert Bevington SHOWTIME REALTY
$12,600 per month
301 Avenida Madera Unit A, Sarasota, FL 34242
Current Availability: 5/19/2024-5/25/2024, 5/30/2024-6/7/2024, 6/23/2024-7/26/2024, 8/24/2024-10/25/2024, 11/3/2024-11/7/2024, 11/17/2024-12/5/2024 If you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is a few blocks to the beach. Beautifully updated, this home
Robert Bevington SHOWTIME REALTY
$7,000 per month
4852 Featherbed Ln, Sarasota, FL 34242
SIESTA KEY, Sarasota, Single Family Pool Home….Well-positioned for convenience and natural attractions . . . and dinners are breezy on your patio! The advantages of this appealing home in the Siesta area of Siesta Key become apparent while you are still walking the perimeter. The clear blue pool and the patio are a perfect pairing of amenities, supporting a variety of social activities and
Jane Hunter JENNETTE PROPERTIES INC
$4,000 per month
1200 E Peppertree Ln Unit 305, Sarasota, FL 34242
3rd floor beautifully appointed. 2 bedroom 2 bath Unit is available Seasonal $7500; Yearly or 6 month rental $4500.000 Underground parking (1) space. Your own private washer and dryer inside unit. Tennis and pickle ball courts. Private Beach with Chairs. 2 heated pools, fitness room, clubhouses, fishing pier. Location is great.
Lisa Beach WATERSIDE REALTY LLC
$8,900 per month
1206 Siesta Bayside Dr Unit 1206B, Sarasota, FL 34242
Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. With breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great
Andy Moore GULF COAST REALTY & MANAGEMENT
$2,500 per month
1300 N Portofino Dr Unit 205, Sarasota, FL 34242
Available now through Dec 2025 for $2,500 per month. Available Jan-Mar 2026 for $6,000 per month. Welcome to your dream coastal escape in beautiful Siesta Harbor on Siesta Key! This turnkey furnished; spacious one-bedroom, two-bath condo is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short
Jonathan OSteen O'STEEN GROUP INC
$4,500 per month
733 Tropical Cir, Sarasota, FL 34242
Availability June 1st for Annual Lease. Welcome to your tropical escape on Siesta Key! This serene 3-bedroom, 2-bath annual rental offers a wide open floor plan with vaulted ceilings, split bedrooms, and a spacious 2-car garage. The stone-accented great room flows effortlessly into the kitchen with a unique breakfast bar, all overlooking the screened-in pool and lush tropical landscaping. Recent
Anthony Dalesandro BRIGHT REALTY
$8,500 per month
1256 Riegels Landing Dr, Sarasota, FL 34242
This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full
Christopher Davenport STARLINK REALTY INC
$3,000 per month
4660 Ocean Blvd Unit Q2, Sarasota, FL 34242
**Beachfront Bliss in Siesta Key? Modern 2 Bed, 2 Bath Condo** Discover this Gulf Front community retreat minutes walk to the heart of Siesta Key Village and #1 sand beach, with this stunning updated open floor plan 2-bedroom, 2-bathroom 2nd level resort living. Move in ready! Nestled along the pristine shores, this unit offers a wonderful blend of modern comfort and coastal charm. Step inside
Adam Sabari LPT REALTY, LLC
$6,500 per month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available May 1, 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet). Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the U.S.! This gem can
Marianne LeBar ROSEBAY INTERNATIONAL REALTY, INC
$6,900 per month
1269 Dockside Place Unit 115, Sarasota, FL 34242
A BOATERS PARADISE! THE BEST OF THE BEACH AND THE BAY!! Great canal front first floor condo with large deck! Best of both worlds - across the street from Siesta Beach and a gated bayside community open to the intracoastal. Large kitchen with granite countertops, open to living/dining room. Bonus Florida room with plantation shuttered sliders that recess for an open air concept. Two bedroom, each
Susan Brooks COLDWELL BANKER SUNSTAR REALTY
$7,000 per month
6006 Midnight Pass Rd Unit 15, Sarasota, FL 34242
No roads to cross to get to the beach! Just listed- clean and cheery one bedroom/one bath condo in Casa Mar is ready for your beach stay! Covered parking, on-site community laundry rooms, and heated pool are just some of the amenities this Association has to offer. A recently added security gate adds value. This condo is ready for your stay- includes linens & beach towels. Pack your suit and
Robert Bevington SHOWTIME REALTY
$4,995 per month
5770 Midnight Pass Rd Unit 405, Sarasota, FL 34242
Immaculate well maintained 2 beds 2 bath condo situated in the desirable Gulf & Bay Club on Siesta Key. This 4th floor unit is meticulously maintained and tastefully decorated. Amenities include three pools, saunas, fitness center, tennis, basketball, racquetball, & 24hr security. A must see! Wake up to views of the Gulf and enjoy living your Siesta Key dream. Available for annual rent at $4,500
Pamala Casey CASEY REALTY CORPORATION
$2,500 per month
111 Pass Key Rd Unit 111, Sarasota, FL 34242
Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ for al fresco dining. The clubhouse is perfect for social
Ray Shope ROSEBAY INTERNATIONAL REALTY, INC
$7,350 per month
524 Beach Rd Unit A, Sarasota, FL 34242
Welcome to YOUR little piece of Paradise: Oceanfront Oasis!! This charming ground floor unit boasts a view of the gulf as you wander down the private path to world-renowned Siesta Key Beach. This home offers two bedrooms & two baths featuring a split floorplan. This unit is only a 10 minute walk from Siesta Village! The 20 ft long screened lanai offers a tranquil view, with room for cocktails or
Robert Bevington SHOWTIME REALTY
$17,000 per month
6006 Midnight Pass Rd Unit 36, Sarasota, FL 34242
Beachfront Bliss at Casa Mar – Siesta KeyDiscover this beautifully updated two-bedroom, two-bathroom beachfront condo in Casa Mar, offering direct access to Crescent Beach, a serene and less crowded alternative to Siesta Key’s main beach.Why You’ll Love This Condo:Prime Beachfront Location – Step right onto the powdery white sands of Crescent BeachClassic Coastal Charm
Robert Bevington SHOWTIME REALTY
$3,950 per month
4708 Ocean Blvd Unit E2, Sarasota, FL 34242
ENJOY INCREDIBLE SUNSETS AND BREATHTAKING VIEWS OF BIG PASS AND DOWNTOWN FROM TWO LARGE BALCONIES, ONE ENCLOSED AND ONE OPEN-AIR! UNIT INCLUDES DESIGNER KITCHEN WITH GRANITE COUNTERS, UPDATED BATHROOM, MARBLE FLOORING, NEW GE PROFILE APPLIANCES, REFRIGERATOR, RANGE, MICROWAVE, AND DISHWASHER. LARGE 2 CAR GARAGE WITH STORAGE CABINETS. CLOSE PROXIMITY TO RESTAURANTS AND SHOPS OF SIESTA VILLAGE.
Curt Cogan COGAN REALTY LLC
$16,000 per month
327 Avenida Milano, Sarasota, FL 34242
Welcome to this amazing Siesta Key vacation home! This beautiful 3 bed/2 bath canal-front beach home is ideally located just a short stroll to Siesta Key Village, with its array of shops, dining options, and entertainment. Situated on a quiet residential street, this home has so much to offer. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with
Chrissie Cummings JENNETTE PROPERTIES INC
$9,000 per month
4822 Ocean Blvd Unit 2F, Sarasota, FL 34242
Gulf Views!!Siesta Key!This 2/2 condo is close to restaurants and outdoor recreation! This captivating 2-bedroom, 2-bathroom condominium is found in Siesta Towers in Siesta Key. The complex is an easy pedestrian distance to Siesta Key Village, and convenient to Siesta Key Beach. The interior welcomes you with stylish fixtures blending seamlessly with bounteous window light and neutral decor. The
Jane Hunter JENNETTE PROPERTIES INC
$5,250 per month
726 Birdsong Ln, Sarasota, FL 34242
AVAILABLE October, November 2025! Currently booked through September 2025. Also booked December - March 2026. WOW! Enjoy a little slice of heaven on the World Famous Siesta Key! This beautifully renovated turnkey 3 bedroom 2 bath, heated pool home, is just a short distance to the #1 rated beaches and the quaint shops and restaurants in the downtown village. Whether it’s our million-dollar
Scott Nold TNG PROPERTY MANAGEMENT
$9,500 per month
1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with
Andy Moore GULF COAST REALTY & MANAGEMENT
$10,500 per month
5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
Available April 2025 this Luxury Siesta Key Beach Front Unit in The Exclusive Gulf and Bay Club... - Enjoy Full Gulf of Mexico Views for the entire month in Paradise of Siesta Key Enjoy panoramic views of the #1 beach in the USA, Siesta Key! This beautiful 2 Bedroom, 2 Bathroom unit is fully updated with hardwood floors, granite countertops, and an amazing amount of cabinet space. Bathrooms are
Robert Bevington SHOWTIME REALTY
$2,600 per month
4660 Ocean Blvd Unit G1, Sarasota, FL 34242
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
Beth Dilley ASCENDIA REAL ESTATE
$8,000 per month
1315 Siesta Bayside Dr Unit 1315B, Sarasota, FL 34242
Welcome to this stunning 2-bedroom, 2-bathroom lakefront condo located on the second floor in Gulf and Bay Bayside, Siesta Key. This two-story retreat features two primary bedrooms, each with a luxurious king-size bed, spacious walk-in closets, and beautifully appointed bathrooms with walk-in showers. In the second floor primary bedroom there is additional sleeping accommodations with a full-size
Andy Moore GULF COAST REALTY & MANAGEMENT
$6,000 per month
5400 Ocean Blvd Unit 1-5, Sarasota, FL 34242
Available 06/03/2025. This gorgeous 1 bedroom 1 bathroom fully furnished unit in the exclusive Terrace building on Siesta Key beach steps away from Siesta Key Village. Enjoy a swim from the elevated pool and catch a sunset with a drink steps away from the unit. This unit includes a private parking spot, direct beach access, WIFI, cable and all utilities included. There is a 60 minimum stay and no
Brenda Cozy COLDWELL BANKER REALTY
$7,500 per month
5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
Discover your own piece of paradise at Jamaica Royale, your unit is 5 steps from the refreshing waters of heated pool #1, while a mere twominute stroll takes you to the pristine Siesta Key beach. Jamaica Royale's prime location on these dazzling sands provides easy access to all. Enjoy assigned covered parking space just steps from your front door. This updated, tastefully decorated
Robert Bevington SHOWTIME REALTY
$7,800 per month
5153 Sandy Cove Ave, Sarasota, FL 34242
You will Never Want to Leave this 4-bedroom house on Siesta Key! Mid-Century Modern, 4 bedroom home with saltwater, heated Pool with canal views. Located within a 6 minute bike ride to Siesta Key's Beach Access #5 and walking distance to everything that Siesta Key Village has to offer. This unique 1950's built, partially renovated, 4 bedroom, 3 full bath, "Sarasota School of Architecture style"
Kelly Anderson RE/MAX ALLIANCE GROUP
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Occupying a barrier island in the Gulf of Mexico off the coast of Sarasota, Siesta Key is home to Siesta Beach, rated the No. 2 beach in the United States by TripAdvisor’s Traveler’s Choice Awards in 2023 and known for its white quartz sand. “Many people find that the sand has a certain energy,” says Dawn Bear, a Realtor with William Raveis Real Estate. While Siesta Beach is destination for travelers, it is also central to the experience of living on the island. “Siesta Key is just a very carefree, wonderful, stress-free community,” says Bear. ...
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