$6,500 per month
- 3 Beds
- 2.5 Baths
- 2,260 Sq Ft
- Condo for Rent
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242$6,500 per month
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242$5,000 per month
735 Birdsong Ln, Sarasota, FL 34242
Looking for the ultimate Siesta Key getaway? This stunning 3-bedroom, 2-bath home offers everything you need for a dream vacation, just 1 mile from the famous Siesta Key Beach and a quick bike ride to the lively Siesta Key Village! Available Nov 1-Dec 21, 2025, and May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the
Scott Nold TNG PROPERTY MANAGEMENT
$20,000 per month
22 Sandy Cove Rd Unit 105W, Sarasota, FL 34242
Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.Every inch of the home has been updated with all-new finishes, furnishings, and a
Cole Collins COLDWELL BANKER REALTY
$3,995 per month
733 Tropical Cir, Sarasota, FL 34242
Siesta Key Custom Pool Home, Vaulted Ceilings and Skylights- Architectural Gem.Welcome to 733 Tropical Circle — a custom-designed retreat tucked away in the heart of Siesta Key. This 3-bedroom, 2-bathroom home offers a unique blend of natural warmth, architectural character, and relaxed coastal charm.Step inside to soaring ceilings with skylights and stunning wood accents that fill
Alyssa Cromie NEXTHOME EXCELLENCE
$14,000 per month
211 Island Cir, Sarasota, FL 34242
AVAILABLE 2026 Season and July-Nov. 2025. 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
Brenda Cozy COLDWELL BANKER REALTY
$5,000 per month
4946 Commonwealth Dr, Sarasota, FL 34242
Discover your perfect slice of "Island Time" at Just Breathe, a serene 3 bedroom, 2.5 bathroom home nestled directly on a peaceful Siesta Key canal. From the moment you arrive, you'll feel the world melt away as you step into this ultimate beach house getaway designed for relaxation and fun. Imagine sipping your morning coffee on the private dock, watching for playful manatees and jumping fish,
Beth Dilley ASCENDIA REAL ESTATE
$5,895 per month
935 Contento St, Sarasota, FL 34242
NEW PRICE! 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
Jennifer Herman MOUNT VERNON PROPERTY MGMT INC
$6,000 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
$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
$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
$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
$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
$15,000 per month
339 Avenida de Paradisio, Sarasota, FL 34242
scape to luxury in our serene Sarasota home! ????Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort.??? Just a 3-Min Drive to Siesta Beach??? 10 Minutes to Crescent Beach????? 13-Min Walk to a Local BeachDiscover the best of Sarasota with us!
Valerie McInerney LPT REALTY, LLC
$11,000 per month
1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
Gulf & Bay Club Bayside offers resort-style amenities, including two heated pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.Guest reservations include beach tags, giving you private beach
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,500 per month
5216 Calle de Costa Rica, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key retreat, perfectly located just a leisurely
Beth Dilley ASCENDIA REAL ESTATE
$13,200 per month
306 Beach Rd Unit 306, Sarasota, FL 34242
Take some time to get away from it all.. we have the perfect place for you and your family to stay! This Spanish style tri-level home is in one of the greatest locations on Siesta Key Beach, Florida. Walk up the windowed staircase to the second floor where you’ll enjoy cooking and hanging out with the family! Enjoy your morning coffee or dinner on the balcony. Time for some fun in the sun! Walk,
Beth Dilley ASCENDIA REAL ESTATE
$8,000 per month
5640 Cape Leyte Dr, Sarasota, FL 34242
It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bathroom singly family home. The open floor plan makes plenty of space to cook in the fully equipped kitchen and hang in the living room or the enclosed lanai overlooking the pool! Take a stroll to the
Beth Dilley ASCENDIA REAL ESTATE
$10,500 per month
5024 Higel Ave, Sarasota, FL 34242
Spectacular is an understatement when describing this updated Siesta Key CANAL FRONT POOL HOME. Once you step inside you'll notice an open-airy floor plan, beautifully decorated to reflect a modern beach-style home! Enjoy the master bedroom with BEAUTIFUL VIEWS of the canal and your very own access to the refreshing POOL and SPACIOUS PATIO! The additional two bedrooms are roomy and private with
Beth Dilley ASCENDIA REAL ESTATE
$8,900 per month
1275 Siesta Bayside Dr Unit 1275B, Sarasota, FL 34242
Welcome to this stunning second-level condo nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal
Andy Moore GULF COAST REALTY & MANAGEMENT
$8,000 per month
1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural
Andy Moore GULF COAST REALTY & MANAGEMENT
$5,000 per month
1391 Siesta Bayside Dr Unit 1391B, Sarasota, FL 34242
Enjoy your vacation on Siesta Key in this spacious three bedroom/two bathroom vacation rental. This condo is turnkey furnished including washer/ dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$7,700 per month
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
Beautiful Key West-style three bedroom, two bath, turnkey furnished condo with its own garage in a lush, tropical resort setting. The townhouse, second/third floor condo, is meticulously maintained and beautifully furnished - There's even a teeny "peek-a-boo" water view from the lanai. The furnishings and flooring are stylish and perfect for the beach. The updated kitchen has granite counter tops
Andy Moore GULF COAST REALTY & MANAGEMENT
$4,700 per month
4900 Ocean Blvd Unit 501, Sarasota, FL 34242
Welcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! With three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the
Beth Dilley ASCENDIA REAL ESTATE
$9,500 per month
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and
Andy Moore GULF COAST REALTY & MANAGEMENT
$12,000 per month
1305 Siesta Bayside Dr Unit 1305B, Sarasota, FL 34242
Enjoy your vacation on Siesta Key in this spacious three bedroom / two bathroom vacation rental. This condo is turnkey furnished including washer / dryer and private garage. Guests are walking distance away from private beach access to Siesta Key’s world-renowned white sandy beach on the Gulf of Mexico. Come stay with us and enjoy warm sunny Siesta Key.**Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$9,300 per month
1272 Siesta Bayside Dr Unit 1272C, Sarasota, FL 34242
Spacious two bedroom/two full bathroom vacation rental at the Gulf and Bay Club Bayside. Private beach access – 5 minute walk. Tile floors throughout and completely re-decorated and furnished with many amenities for your family’s enjoyment. King bed in the master and two doubles in the guest room.*Taxes and fees not included.
Andy Moore GULF COAST REALTY & MANAGEMENT
$15,000 per month
5516 Avenida Del Mare, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 5th - February 6th 2026, April 2026. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kiddos
Beth Dilley ASCENDIA REAL ESTATE
$18,000 per month
345 Avenida Leona, Sarasota, FL 34242
Listing reflects peak season rate. Available peak season months: January 2026, February 2026, March 2026, April 2026. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a
Beth Dilley ASCENDIA REAL ESTATE
$5,900 per month
1660 Summerhouse Ln Unit 301, Sarasota, FL 34242
LOCATION, LOCATION, LOCATION!!! Stunning large luxury condo located in the sought after community of Summer Cove on Siesta Key is available for an ANNUAL LEASE. This corner unit, light and bright property has been meticulously professionally decorated and it shows. Three bedrooms, three and a half bathrooms, turnkey furnished, three open lanais that face east and west, living room/kitchen/dining
C. Alison Hunter JENNETTE PROPERTIES INC
$3,900 per month
4660 Ocean Blvd Unit B2, Sarasota, FL 34242
SIESTA KEY WATERFRONT UNIT AVAILABLE AS FURNISHED LONG TERM. Sea Village offers million dollar views and is situated on 5 acres overlooking the Gulf. It provides a peaceful retreat with opportunities to witness breathtaking sunsets, the full moon reflecting on the water, and serene walks to the beach and Siesta Village. Additionally, its location on the north end of the Key provides convenient
Margaret Young JENNETTE PROPERTIES, INC.
$30,000 per month
95 Sandy Hook Rd S, Sarasota, FL 34242
6 Month Minimum... Private Beach! Private Beach! Private Beach! SANDY HOOK's "BEACH-COMER COTTAGE" Available NOW!!!!!!! IN SANDY HOOK, DIRECTLY ON THE GULF AT BIG PASS. ENJOY YOUR OWN private Beach!!!TROPICAL PARADISE. SIESTA KEY'S "OUTDOOR ACADEMY"!!! ONLY 1/2 MILE AWAY! One-of-a-kind enclave of Sandy Hook at USA's No 1 BEACH. A private road takes you to Elevated living area with entry
Joseph Russo COURTYARD MODERN