Siesta Key, FL Houses for Rent

• 

  

  

  /9

  $10,770 per month

  • 2 Beds
  • 2 Baths
  • 1,043 Sq Ft
  • House for Rent

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242

  We welcome you to stay in our updated oceanfront condo on Siesta Key Crescent Beach - the best beach in Florida! Our spacious 2 bed/2 bath oceanfront home is 1080 square feet with an ocean view that cannot be beat! Unit #206 is part of the Casa Blanca Vacation Beach Resort, and the crystal white sand is steps away! Remodeled in 2023, fully equipped kitchen with quiet dishwasher, spacious living

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6154 Midnight Pass Rd Unit 206, Sarasota, FL 34242
• 

  

  

  /20

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242

  Starting at $179/night! Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, featuring a king-sized bed in the primary suite and a comfortable sleeper sofa in the living area. This stylish retreat boasts a fully equipped kitchen adjoining a spacious dining area, ideal for entertaining or relaxing meals. Enjoy the convenience of a private carport just steps from your door, while

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 53, Sarasota, FL 34242
• 

  

  

  /25

  $7,650 per month

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242

  Starting at $255/night! Experience the ultimate beachfront getaway at Villa 40, a beautifully appointed 2-bedroom, 2-bathroom condo at Casa Mar, thoughtfully designed to accommodate up to six guests in comfort and style. This spacious retreat features a king bed in the primary bedroom, two twin beds in the second bedroom, and a queen air mattress for added flexibility. The fully equipped kitchen

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 40, Sarasota, FL 34242
• 

  

  

  /16

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242

  Starting at $179/night! Step into your perfect beach getaway with this charming ground-floor 1-bedroom unit located in the sought-after Casa Mar complex, just off Midnight Pass Road and only steps from the sand. Relax on the screened lanai overlooking a peaceful courtyard, where two sparkling pools invite you to unwind in the Florida sunshine. A short stroll along the sidewalk brings you directly

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 24, Sarasota, FL 34242
• 

  

  

  /28

  $5,370 per month

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242

  Starting at $179/night! Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 44, Sarasota, FL 34242
• 

  

  /21

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242

  Starting from $179/night! Experience the charm of Villa 54, a 1-bedroom, 1-bathroom retreat at Casa Mar. Relax in the luxurious king-sized bed in the master bedroom, complemented by a cozy sleeper sofa in the spacious living area. Prepare gourmet meals in the fully equipped kitchen that seamlessly flows into an elegant dining space, perfect for entertaining or quiet meals. Outside, enjoy the

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 54, Sarasota, FL 34242
• 

  

  /24

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242

  Starting at $179/night. Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, where comfort and style meet just steps from the beach. The spacious primary suite features a king-sized bed, while the fully equipped kitchen flows seamlessly into a generous dining area and inviting living room, perfect for relaxing or entertaining. Step outside to enjoy a screened-in lanai furnished

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 22, Sarasota, FL 34242
• 

  

  /24

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 65, Sarasota, FL 34242

  Starting at $179/night! Discover a luxurious 1-bedroom, 1-bathroom condominium at Casa Mar, featuring a king-sized bed in the primary suite and a comfortable sleeper sofa in the living area. This stylish retreat offers a fully equipped kitchen adjacent to a spacious dining area, ideal for entertaining. A convenient stackable washer and dryer is located within the unit, adding to your comfort and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 65, Sarasota, FL 34242
• 

  

  /22

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 64, Sarasota, FL 34242

  Starting at $179/night! Step into your perfect getaway at this charming ground-floor 1-bedroom unit nestled within the Casa Mar complex, just steps from the beach off Midnight Pass Road. Relax on the screened lanai overlooking a tranquil courtyard, where not one but two inviting pools beckon you to unwind. A leisurely stroll along the sidewalk leads you straight to the sandy shores. Enjoy the

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 64, Sarasota, FL 34242
• 

  

  /19

  $5,070 per month

  • 1 Bath
  • 420 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 29, Sarasota, FL 34242

  Starting at $169/night. Discover the perfect beach getaway at our charming studio on beautiful Siesta Key, just steps from the world-famous white sands of Siesta Beach. Ideal for couples or solo travelers, this cozy and well-appointed retreat offers everything you need for a relaxing escape. Nestled in the heart of Siesta Key, you’ll be within easy walking distance of the beach, local shops, and

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 29, Sarasota, FL 34242
• 

  

  /30

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242

  Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
• 

  

  /26

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242

  Starting at $179/night! Welcome to your vibrant beachside retreat! This inviting 1-bedroom, 1-bathroom condo is the perfect gateway to both relaxation and adventure. Prepare delicious meals in the fully equipped kitchen and enjoy them in the cozy nearby dining area. Convenience is a priority with your own private carport just steps from the door. At Casa Mar, indulge in resort-style amenities

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 63, Sarasota, FL 34242
• 

  

  /24

  $6,300 per month

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242

  Starting at $210/night! Escape to coastal comfort in this charming 2-bedroom villa just steps from the beach. This beautifully furnished retreat boasts a bright and airy living space with vaulted ceilings, exposed wood beams, and abundant natural light. The open-concept living area features cozy seating, a large flat-screen TV, and stylish coastal décor that perfectly blends comfort with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 58, Sarasota, FL 34242
• 

  

  /18

  $8,970 per month

  • 1 Bath
  • 435 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242

  Starting at $299/night! Explore a luxurious studio-style condominium at Casa Mar, featuring one bathroom and a queen-sized murphy bed. This elegant retreat boasts a fully equipped kitchen that flows into a spacious dining area, ideal for hosting guests. Benefit from the convenience of a private carport just a few steps away from your residence. Casa Mar offers an impressive range of amenities,

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 68, Sarasota, FL 34242
• 

  

  /15

  $5,070 per month

  • 1 Bath
  • 420 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242

  Starting at $154/night! Escape to the perfect beachside retreat at our charming and cozy studio on beautiful Siesta Key. Just steps from the world-renowned white sands of Siesta Beach, this inviting space is ideal for couples or solo travelers looking to unwind in comfort. The studio features two plush queen-size beds, a relaxed seating area, and a flat-screen TV for your entertainment. Prepare

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 2, Sarasota, FL 34242
• 

  

  /20

  $5,070 per month

  • 1 Bath
  • 435 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242

  Starting at $169/night. Discover the perfect beach getaway at our charming studio, ideally located on the beautiful Siesta Key. Just steps from the pristine white sands of Siesta Beach, this cozy, well-appointed retreat is perfect for couples or solo travelers seeking a relaxing escape. The studio features a comfortable queen-size bed, a cozy seating area, and a flat-screen TV for your

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 10, Sarasota, FL 34242
• 

  

  /22

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 5, Sarasota, FL 34242

  Starting at $179/night! Welcome to your vibrant beachside retreat—a beautifully renovated 1-bedroom, 1-bathroom oasis where modern comfort meets coastal charm. Thoughtfully designed with relaxation in mind, the serene bedroom features a deluxe queen bed dressed in premium linens, perfect for restful nights after sun-filled days. The fully equipped kitchen boasts modern appliances, cookware, and a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 5, Sarasota, FL 34242
• 

  

  /21

  $5,370 per month

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft
  • House for Rent

  6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242

  Starting at $179/night! Welcome to your vibrant beachside retreat! This charming ground-level condo features a spacious bedroom with a king bed, a sleeper sofa in the living room, and a full bathroom—perfect for relaxation and adventure. Whip up delicious meals in the fully equipped kitchen and enjoy them in the cozy dining area nearby. Convenience is at your fingertips with your own private

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  6006 Midnight Pass Rd Unit 71, Sarasota, FL 34242
• 

  

  /19

  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • House for Rent

  143 Whispering Sands Dr, Sarasota, FL 34242

  Available for season March and April 2026! This 2 bedroom 2 bath villa with easy ground floor entry features tile flooring in the main living areas and plush new carpeting in the bedrooms. The stylish galley kitchen has been fully updated with custom white cabinetry, granite countertops and backsplash, recessed lighting, and brand-new GE appliances, perfect for preparing meals after a day at the

  Maureen Plichta STRINGER MANAGEMENT INC

  143 Whispering Sands Dr, Sarasota, FL 34242
• 

  

  /34

  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,210 Sq Ft
  • House for Rent

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242

  Welcome to your bright and inviting Siesta Key vacation retreat! Enjoy deeded beach access to the stunning Siesta Key Beach, just steps away, where sun and surf await. Relax by Siesta Key’s largest heated pool or unwind in the lush, park-like setting with peaceful bay views. Explore the nearby vibrant Village on Siesta Key, filled with diverse dining, unique shops, and lively events. With

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  6005 Midnight Pass Rd Unit S4, Sarasota, FL 34242
• 

  

  /27

  $2,800 per month

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft
  • House for Rent

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242

  Welcome to Sunrise Porch Lookout — your peaceful intercoastal retreat in the heart of Siesta Key. This bright and tropical second-floor condo is perfectly situated in the highly sought-after Provincial Gardens community, where Old Florida charm meets serene waterfront beauty. Overlooking the intercoastal waterway and lush park-like lawn, the screened-in wraparound porch is your front-row seat to

  Susan Saltalamacchia CONCESSION REAL ESTATE COMP.

  6005 Midnight Pass Rd Unit N13, Sarasota, FL 34242
• 

  

  /42

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • House for Rent

  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 May 1-Nov 21, 2026. 30 day minimum stay, NOT available annually. Fully turnkey furnished, this home is ready to welcome you the moment you step inside. The

  Scott Nold TNG PROPERTY MANAGEMENT

  735 Birdsong Ln, Sarasota, FL 34242
• 

  

  /36

  $14,000 per month

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • House for Rent

  211 Island Cir, Sarasota, FL 34242

  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

  Brenda Cozy COLDWELL BANKER REALTY

  211 Island Cir, Sarasota, FL 34242
• 

  

  /45

  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • House for Rent

  4879 Commonwealth Dr, Sarasota, FL 34242

  Lease a Rare Piece of Sarasota's Architectural History on Siesta Key! Step into timeless design and architectural significance with this rare mid-century modern masterpiece, situated on a private double lot in the heart of Siesta Key. Originally crafted in 1957 by Frank Coleman and Tollen Twitchell, two influential figures in the Original Sarasota School of Architecture, this home seamlessly

  Daniel Petrilla PREFERRED SHORE LLC

  4879 Commonwealth Dr, Sarasota, FL 34242
• 

  

  /55

  $5,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  4946 Commonwealth Dr, Sarasota, FL 34242

  Available as a monthly rental starting in May. 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,

  Beth Dilley ASCENDIA REAL ESTATE

  4946 Commonwealth Dr, Sarasota, FL 34242
• 

  

  /91

  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,341 Sq Ft
  • House for Rent

  412 Treasure Boat Way, Sarasota, FL 34242

  Discover your dream home with this exquisite single family residence available for annual rental. This remarkable property redefines elegance and comfort, featuring stunning one-of-a-kind architecture that combines exceptional design with spacious living. Crafted for discerning tenants who appreciate the finer things in life, the home boasts four generously sized bedrooms and three luxurious

  Beth Dilley ASCENDIA REAL ESTATE

  412 Treasure Boat Way, Sarasota, FL 34242
• 

  

  /13

  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • House for Rent

  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

  Timothy Bloch QUEST PROPERTIES INC

  306 Island Cir, Sarasota, FL 34242
• 

  

  /18

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  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

  301 Avenida Madera Unit B, Sarasota, FL 34242
• 

  

  /34

  $12,600 per month

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  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,

  Robert Bevington SHOWTIME REALTY

  301 Avenida Madera Unit A, Sarasota, FL 34242
• 

  

  /79

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,439 Sq Ft
  • House for Rent

  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

  4852 Featherbed Ln, Sarasota, FL 34242
• 

  

  /40

  $6,500 per month

  • 3 Beds
  • 4 Baths
  • 2,168 Sq Ft
  • House for Rent

  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

  1256 Riegels Landing Dr, Sarasota, FL 34242
• 

  

  /84

  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft
  • House for Rent

  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. As you enter this exquisite home, you will find original and restored terrazzo floors, wood beams with modern finishes. The beautifully

  Chrissie Cummings JENNETTE PROPERTIES INC

  327 Avenida Milano, Sarasota, FL 34242
• 

  

  /56

  $5,525 per month

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • House for Rent

  726 Birdsong Ln, Sarasota, FL 34242

  AVAILABLE after April 15, 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 sunsets, endless watersports activities, Sunday’s famous Drum Circle, or to just

  Scott Nold TNG PROPERTY MANAGEMENT

  726 Birdsong Ln, Sarasota, FL 34242
• 

  

  /80

  $8,500 per month

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • House for Rent

  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

  5216 Calle de Costa Rica, Sarasota, FL 34242
• 

  

  /58

  $8,000 per month

  • 3 Beds
  • 2 Baths
  • 2,002 Sq Ft
  • House for Rent

  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

  5640 Cape Leyte Dr, Sarasota, FL 34242
• 

  

  /41

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • House for Rent

  5577 Contento Dr, Sarasota, FL 34242

  This is a short term rental. Listing reflects off season rate. Available peak season month: January 3rd - 31st, 2026. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits in this 2-bedroom, 2-bathroom saltwater pool home, perfectly situated on a peaceful canal. We're delighted to be dog-friendly, offering a fantastic space for everyone. Step inside to a meticulously

  Beth Dilley ASCENDIA REAL ESTATE

  5577 Contento Dr, Sarasota, FL 34242
• 

  

  /60

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 2,259 Sq Ft
  • House for Rent

  5516 Avenida Del Mare, Sarasota, FL 34242

  This is a short term rental. 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

  Beth Dilley ASCENDIA REAL ESTATE

  5516 Avenida Del Mare, Sarasota, FL 34242
• 

  

  /98

  $18,000 per month

  • 3 Beds
  • 2 Baths
  • 1,617 Sq Ft
  • House for Rent

  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

  345 Avenida Leona, Sarasota, FL 34242
• 

  

  /25

  $12,000 per month

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft
  • House for Rent

  5519 Azure Way, Sarasota, FL 34242

  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 large and/or multiple families and guests who want to enjoy either the pool or the beach without getting in the car! A brand new beautiful granite topped Kitchen space opens to a family room all

  Catherine Foley JENNETTE PROPERTIES, INC.

  5519 Azure Way, Sarasota, FL 34242

Showing Results 81 - 120, Page 3 of 3