Siesta Key, FL Homes for Rent with Pool

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  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242

  2 BR - 2 BA - 6 person Max - Highrise - Pond View - Approx. 75 yards from beach This property is a 30 night minimum. Only steps from the beautiful Crescent Beach. This luxurious 2 bedroom and 2 full bathroom unit has it all. The unit is in a gulf side high rise building on the 2nd floor. Assigned covered parking located in the parking garage under the building. A luxurious dining area greets you

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 206AA, Sarasota, FL 34242
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  /22

  $9,550 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242

  Discover modern comfort in this stylishly updated 2BR/2BA vacation rental condo. Perfect for relaxation and rejuvenation, this well-appointed space offers everything you need for a memorable getaway. Enjoy garden views from the lanai. Modern amenities include new coastal-inspired furniture and stainless steel appliances. Enjoy community pool access for refreshing dips after beach days. Bask in

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 407, Sarasota, FL 34242
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  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 501, Sarasota, FL 34242

  2 BR -- 2 BA -- 4 Person Max -- High Rise -- Beach and Pond View1125-501 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx. 175 yards away from Crescent beach.Open kitchen floor plan with recessed lighting. Granite counters, Stainless steel fridge. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai).Condo

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 501, Sarasota, FL 34242
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  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 102, Sarasota, FL 34242

  A 3 month stay is preferred but will accept a 2 month stay, possible 1 month. Call the office for details.Luxuriously remodeled 2 bedroom 2 full bath unit on the first floor in a gulf side high-rise building.The unit has updated wood tiles throughout, ceiling fans in each room, recessed and updated lighting.The kitchen is fully updated with stainless steel appliances, gorgeous counter

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 102, Sarasota, FL 34242
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  $9,225 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 402, Sarasota, FL 34242

  Stylish 2-Bedroom, 2-Bathroom Condo in Peppertree Bay - Siesta Key, FLLooking for the perfect vacation getaway? This stunning 2-bedroom, 2-bathroom condo in the desirable Peppertree Bay community is just what you need! Nestled on the fourth floor, this high-rise retreat offers tranquil pond views and a serene atmosphere.The unit features assigned covered parking under the building for

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 402, Sarasota, FL 34242
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  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242

  2 BR - 2 BA - 4 Person Max - Gulf side - Mid-Rise - Approx.150 yards from beach This property is a 30 night minimum.This 2-bedroom, 2 bath located on the gulf side is approx. 150 yards from the beach. This unit is on the 7th floor, accessible via elevator or stairs. Plenty of room for dining at the 6-service dining table. Couches, a ceiling fan, and TV in the living room for

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 707, Sarasota, FL 34242
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  $8,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242

  Second-Floor Condo in Sought-After Peppertree Bay. 30 day minimum stay. Starting between $250-$347/night!Welcome to this beautifully maintained second-floor condo located in the highly desirable Peppertree Bay community on Siesta Key. Offering a tranquil pond view, this residence provides a peaceful coastal retreat just steps from the Gulf.The condo features a full kitchen equipped with

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 202, Sarasota, FL 34242
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  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 702, Sarasota, FL 34242

  This property is a 30 night minimum. This 2 bedroom, 2 bath is in a Gulf-side High-rise unit, located approximately 175 yards from Crescent Beach.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and beautiful views of the beach through the lanai sliding glass doors. The master bathroom has a tub/shower combination with updated finishes and grab bars.The guest bedroom has a

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 702, Sarasota, FL 34242
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  $11,105 per month

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft
  • Apartment for Rent

  1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242

  This property is a 30 night minimum. This 2 bedroom, 2 full bath unit is located in a Gulfside Highrise, only steps from Crescent Beach. An open concept living space flows nicely from the formal dining to spectacular views of Peppertree Pond on the lanai. The living area has plenty of comfortable seating for the entire family, a 55" Smart TV, and glass door lanai access. The kitchen has been

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1055 W Peppertree Dr Unit 207AA, Sarasota, FL 34242
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  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 701, Sarasota, FL 34242

  2 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 yards from Crescent Beach.The master bedroom has a king bed, a 20 inch TV, a ceiling fan, and beautiful views of the beach through the lanai sliding glass doors. The master bathroom has a tub/shower combination

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 701, Sarasota, FL 34242
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  $6,650 per month

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Apartment for Rent

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242

  This property is a 30 night minimum.1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach.Open kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage.Approx. 1200 Sq. Ft. (1480 including the lanai). Condo

  Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

  1125 W Peppertree Dr Unit 705, Sarasota, FL 34242
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  /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
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  $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
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  $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
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  $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
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  /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
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  /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
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  $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
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  /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
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  /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
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  $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
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  $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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  $7,900 per month

  • 2 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Condo for Rent

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242

  Still available for season January - April 2026l! Two bedroom 2 bath ground floor with view of the Gulf. Step outside and your on the sand! Escape the winter and be on the beach. Located in the heart of Siesta Key’s most desirable area, this property offers exceptional appeal with being just steps from the world-famous powdery white sand beach. Siesta Key Village is within easy walking distance,

  Maureen Plichta STRINGER MANAGEMENT INC

  19 Whispering Sands Dr Unit 106, Sarasota, FL 34242
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  $6,500 per month

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft
  • Condo for Rent

  5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242

  This luxury Siesta Key beachfront unit in the exclusive Gulf and Bay Club offers full panoramic views of the Gulf of Mexico and the #1 beach in the USA, Siesta Key! This beautifully updated 2-bedroom, 2-bathroom unit features hardwood floors, granite countertops, and an abundance of cabinet space. The bathrooms are elegantly updated with tile and granite counters, making this a truly turnkey

  Robert Bevington SHOWTIME REALTY

  5740 Midnight Pass Rd Unit 303, Sarasota, FL 34242
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  /21

  $8,500 per month

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Apartment for Rent

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242

  Newly remodeled and furnished “Bougie beach bungalow” on Siesta Key Island. This Condo will “wow” you from the first moment you enter. Just say Alexa turn lights on and your command will be answered. This condo is on the first floor and it’s just a few minutes walk from the siesta key public beach access. The community is very welcoming to all guest and has a heated pool year-round and also many

  Stephanie Fox EXP REALTY LLC

  5623 Midnight Pass Rd Unit 615, Sarasota, FL 34242
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  $6,000 per month

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Condo for Rent

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242

  **FULLY REMODELED, GROUND FLOOR CONDO, ACROSS FROM SIESTA KEY BEACH ** Seasonal Rental only, $6,900/mo plus fees, Minimum Stay required Sandy Feet Retreat is a fully remodeled ground-floor condo located directly across the street from Siesta Key’s main beach access. Recently updated throughout, the residence features a brand-new kitchen with modern appliances, beautifully renovated bathrooms, and

  Dave Holt PMI SOUTHWEST FLORIDA

  5600 Beach Way Dr Unit 113, Sarasota, FL 34242
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  /16

  $3,400 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  4660 Ocean Blvd Unit P1, Sarasota, FL 34242

  Long term rental turnkey furnished waterfront condo in the desirable Sea Village community. Enjoy stunning views of Big Pass and the Gulf, plus easy access to the community pool. The home features travertine flooring, crown molding, hurricane-rated sliders, plantation shutters, and an open living/dining layout. The kitchen includes wood cabinetry, granite countertops, a breakfast bar, and quality

  Nelson Reyes SHOWTIME REALTY

  4660 Ocean Blvd Unit P1, Sarasota, FL 34242
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  $5,600 per month

  • 2 Beds
  • 2 Baths
  • 929 Sq Ft
  • Condo for Rent

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242

  Available for season 2026! Welcome to Coastal Living at its finest, perfectly nestled on the sought after barrier island of Siesta Key. Updated unit offers serene water views, abundant natural light and the relaxed elegance that defines Florida living. Located in a meticulously maintained waterfront community, this spacious unit features an open and inviting layout ideal for seasonal

  Angela Bailey MONARCH PROPERTY GROUP LLC

  1250 N Portofino Dr Unit 303, Sarasota, FL 34242
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  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Condo for Rent

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242

  AVAILABLE again starting April 1, 2026! Experience the best of Siesta Key living in this beautifully updated 2-bedroom, 2-bathroom condo at the sought-after Harbor Towers Yacht & Racquet Club. Fully furnished and thoughtfully renovated, this 1,056 sq ft residence offers a perfect blend of comfort and luxury. The primary suite has a king-sized bed and en-suite bath, while the guest bedroom

  Anna Williams SHOWTIME REALTY

  5855 Midnight Pass Rd Unit 404, Sarasota, FL 34242
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  /19

  $7,500 per month

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

  143 Whispering Sands Dr, Sarasota, FL 34242

  Available for season 2027! 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 beach.Enjoy

  Maureen Plichta STRINGER MANAGEMENT INC

  143 Whispering Sands Dr, Sarasota, FL 34242
• 

  

  /19

  $6,950 per month

  • 2 Beds
  • 2 Baths
  • 1,217 Sq Ft
  • Condo for Rent

  1249 Dockside Place Unit 110, Sarasota, FL 34242

  LOCATION LOCATION LOCATION! Welcome beach lovers. This 2 bedroom, 2 bath first floor condo with a one car garage on Siesta Key will fulfill all your dreams! Spend the day on the famous Siesta Key Beach (just steps away) then take a sunset boat! Play tennis/pickle ball on the private courts, lounge by the pool or fish out your back door. This condo is being offered turnkey furnished. Updated

  Marisa Marino BRIGHT REALTY

  1249 Dockside Place Unit 110, Sarasota, FL 34242
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  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Condo for Rent

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242

  Available April 2026 and Beyond! The rate shown reflects the annual rental price. Seasonal rates for April 2026 may vary. Don’t miss the opportunity to secure this property, reach out for availability and details. Step into paradise at Casarina, a beautifully maintained beachfront community right on Siesta Key’s world-famous Crescent Beach. With 200 feet of private beach access, you’re just steps

  Cole Collins COLDWELL BANKER REALTY

  5880 Midnight Pass Rd Unit 306, Sarasota, FL 34242
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  $7,500 per month

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft
  • Condo for Rent

  5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

  Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

  Robert Bevington SHOWTIME REALTY

  5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
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  /70

  $7,500 per month

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft
  • Condo for Rent

  1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

  This is a short term rental. Listing reflects peak season rate. Available peak season months: January 2026, February 2026, April 2026. Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the

  Beth Dilley ASCENDIA REAL ESTATE

  1137 N Moonmist Ct Unit L7, Sarasota, FL 34242

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