AVAILABLE 2025 SEASON... 90 DAY MIN.AVAILABLE APR.-DEC. 2024...30 DAY MIN.Fabulous pool home located in one of Siesta Keys most sought after areas. Interior is nicely furnished. Take a late night swim
SIESTA KEY, Adorable 2/2 SFH with a private saltwater pool for the wonderful beach getaway. This house is located near by the award winning Siesta Key Beach(5 minutes away) and Siesta Village((two min
An Ascendia Group Property! **Listing reflects off season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,600/month), (MAY - DEC - off season: $4,500/month). Available beginn
NEW LISTING! The Sugar Shak (SK) - Charming shiplap Florida Cyprus cottage, 100% Private, perfectly located in Siesta Village! Leave the car behind and walk to all Siesta Key's Top Attractions. Entert
An Ascendia Property! **Listing reflects peak season rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $8,500/month), (MAY - DEC - off season: $5,500/month). The rental rate in th
Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for
Current Availability: After 4/5/2025 Beautiful ground floor 2 bedroom and 2 bathroom condo gulf front on #1 rated Siesta Key Beach!! Walk down our private beach path from our screened in lanai to the
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$7,350/mo
2 beds2 baths980 sq ft
524 Beach Rd Unit B, Sarasota, FL 34242
Parking • A/C • Dishwasher
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Amazing opportunity, to find a rental like this hidden gem! Live your best life with the island lifestyle and enjoy the best of both worlds with the beach and boating. DEEP SAILBOAT WATER BOATING or t
An Ascendia Property! The Keylime Retreat is our newest addition to our vacation property portfolio! (**PLEASE NOTE THE POOL WILL BE UNDER CONSTRUCTION AND NOT AVAILABLE FOR USE DURING SEPTEMBER 2024!
An Ascendia Property! **WEEKLY STAYS AVAILABLE! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Take some time to get away from it all
Available June 1 - November 1. 2 BR - 2 BR - 4 Person Max6018 is a Gulf-side High-rise unit, located approximately 50 yards away from Crescent Beach. Fans located in both bedrooms, kitchen and the lan
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$4,800/mo
2 beds2 baths1,180 sq ft
6018 W Peppertree Way Unit 203, Siesta Key, FL 34242
AVAILABLE 2025 SEASON & MAY - DEC. 2024 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.
Welcome to our stunning vacation rental condo in Siesta Key, Florida! This magnificent 3 bedroom, 2 and a half bath condo offers the perfect tropical escape. With its prime location on the 8th floor o
Want to be able to walk three blocks to Siesta Key beach? Vacation here and you can! This private 3 bedroom 2 1/2 bathroom pool home is warm and inviting and lushly landscaped. There is large screen
Available June 1 - December 12 BR - 2 BA - 4 Person Max - High Rise - Beach ViewThis property is a 30 night minimum. This 2 bedroom, 2 bath is in a Gulf-side High-rise unit, located approximately 175
An Ascendia Property! Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing! Picture this: you roll out of bed and grab your coffee, take two s
AVAILABLE FOR 2025 SEASON. Explore the charm of WHITE SANDS VILLAGE, conveniently located just opposite Siesta Key Beach Access. Revel in the updated 2-bedroom, 2-bathroom 2nd floor condo, tucked away
An Ascendia Property! **Listing reflects off season monthly rate. Monthly rental rates as follows: (JANUARY - APRIL - peak season: $5,500/month), (MAY - DECEMBER - off season: $3,000/month). Available
**BOOKED JANUARY THROUGH MARCH 2025** INCREDIBLE SOUTHWESTERN GULF VIEWS OVERLOOKING WORLD FAMOUS SIESTA KEY BEACH! ** This rarely available 3-bedroom unit located in the E building which is one of th
** BOOKED JANUARY THROUGH MARCH 2025 ***GORGEOUS BEACHFRONT HOME LOCATED IN THE HIGHLY SOUGHT AFTER GULF & BAY COMMUNITY! Enjoy spectacular sunsets and views of the Gulf of Mexico from this 6th floor
LUXURY SIESTA KEY CONDO LIVING ..A beautiful Turnkey 2 bedroom/2 bathroom Penthouse Condominium Plus Den/Office overlooking Sarasota Bay and the Intracoastal Waterway. A king size bed is in the master
Available September 1 - December 1Stylish 2 bedroom/2 bathroom condo in the Peppertree Bay community in Siesta Key Sarasota, FL. Enjoy pond views from this fourth floor high-rise retreat. Modern ameni
DIRECT GULF VIEW/SIESTA KEY/SARASOTAClose to local conveniences! This lovely 2-bedroom, 2.5-bathroom condominium is perfectly situated only steps away from the famous Siesta Key Beach and convenient d
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 a
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$5,000/mo
3 beds2 baths1,495 sq ft
1391 Siesta Bayside Dr Unit 1391B, 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 re
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$9,500/mo
3 beds2 baths1,835 sq ft
1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
Available June 1 - October 12 BR - 2 BA - 6 Person Max - High-rise - Landscape View This property is a 30 night minimum. Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 fu
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$3,800/mo
2 beds2 baths1,105 sq ft
1080 W Peppertree Ln Unit 403A, Sarasota, FL 34242
Welcome to your Gulf & Bay Club Bayside sanctuary in the heart of Siesta Key, FL! This second-story bay front condo offers a blissful retreat with breathtaking views of the azure waters. With two bedr
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$8,100/mo
2 beds2 baths1,420 sq ft
1373 Siesta Bayside Dr Unit 1373C, Sarasota, FL 34242
Indulge in the ultimate relaxation experience at our exquisite vacation rental in Gulf and Bay - Bayside on Siesta Key. This meticulously appointed condo offers an abundance of space and comfort, allo
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$7,200/mo
2 beds2 baths959 sq ft
1374 Siesta Bayside Dr Unit 1374D, Sarasota, FL 34242
Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay,
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$8,000/mo
2 beds2 baths1,280 sq ft
1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
Siesta Key Spectacular Furnished Two bedroom rental located in Bay Tree Club. Available short term from May- December 2024. ( Not available during winter). This stunning brand-new luxury remodel will
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$4,500/mo
2 beds2 baths1,200 sq ft
8625 Midnight Pass Rd Unit B304, Sarasota, FL 34242
Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park yo
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$9,900/mo
2 beds2 baths1,280 sq ft
1365 Siesta Bayside Dr Unit 1365C, 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 unparallel
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$8,000/mo
3 beds3 baths1,835 sq ft
1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
This fabulous one bedroom, plus a full sleep-in den, provides additional space for a quiet sitting room or a guest retreat. Relax in the spacious living area or enjoy a glass of wine on the lanai.The
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$7,000/mo
2 beds1 bath959 sq ft
1360 Siesta Bayside Dr Unit 1360D, Sarasota, FL 34242
Discover the epitome of luxury living in this stunning, custom-designed Italian villa, nestled in the serene Tortoise Estates. This exquisite four-bedroom, three-bathroom residence offers direct deede
Embrace coastal living in this inviting 2-bedroom, 2-bathroom first-level condo nestled within the prestigious Gulf & Bay Club Bayside in Siesta Key, Florida. Step inside to discover a thoughtfully de
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$8,500/mo
2 beds2 baths1,280 sq ft
1364 Siesta Bayside Dr Unit 1364C, Sarasota, FL 34242
Relax in the spacious living area or enjoy a glass of wine on the lanai.This condo is turnkey furnished including washer /dryer and private garage. Guests are walking distance away from private beach
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$7,200/mo
1 bed1 bath959 sq ft
1351 Siesta Bayside Dr Unit 1351D, 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 an
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$7,700/mo
3 beds2 baths1,495 sq ft
1350 Siesta Bayside Dr Unit 1350B, Sarasota, FL 34242
Available June 1 - December 1.Discover modern comfort in this stylishly updated 2BR/2BA vacation rental condo. Perfect for relaxation and rejuvenation, this well-appointed space offers everything you
Based on information submitted to the MLS GRID as of Sun Jun 09 2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.