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Homes for Rent near Out-Of-Door Academy

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  • 3700 S Osprey Ave Unit 214, Sarasota, FL 34239
    3700 S Osprey Ave Unit 214, Sarasota, FL 34239
    3700 S Osprey Ave Unit 214, Sarasota, FL 34239
    /36

    $2,800 per month

    • 2 Beds
    • 1 Bath
    • 991 Sq Ft
    • Apartment for Rent

    3700 S Osprey Ave Unit 214, Sarasota, FL 34239

    Plaza Gardens is the perfect place to call home if you are looking for a peaceful retreat with a touch of luxury. The tropical greenery and well-maintained gardens throughout the building give it a boutique feel, making it the perfect place for those who appreciate a tranquil and serene environment. Situated just southeast of Siesta Key's North Bridge and west of the trail, this condo offers easy

    Andrea Cohen COLDWELL BANKER REALTY

    3700 S Osprey Ave Unit 214, Sarasota, FL 34239
  • 1608 Bayhouse Point Dr Unit 304, Sarasota, FL 34231
    1608 Bayhouse Point Dr Unit 304, Sarasota, FL 34231
    1608 Bayhouse Point Dr Unit 304, Sarasota, FL 34231
    /20

    $1,800 per month

    • 2 Beds
    • 2 Baths
    • 1,318 Sq Ft
    • Condo for Rent

    1608 Bayhouse Point Dr Unit 304, Sarasota, FL 34231

    AVAILABLE June 1, 2026, to December 31 2026. Pelican Cove is located in South Sarasota. West of the trail!!! This 2/2, 1st Floor unit in Pelican Cove is a must-see. Come live the Florida lifestyle! Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include an 86-slip boat harbor with

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    1608 Bayhouse Point Dr Unit 304, Sarasota, FL 34231
  • 1345 2nd St Unit C, Sarasota, FL 34236
    1345 2nd St Unit C, Sarasota, FL 34236
    1345 2nd St Unit C, Sarasota, FL 34236
    /57

    $6,200 per month

    • 4 Beds
    • 2.5 Baths
    • 3,130 Sq Ft
    • Condo for Rent

    1345 2nd St Unit C, Sarasota, FL 34236

    Look at this great location Downtown Sarasota. Walk to everything. This commercial building is 3 floors with spa lounge on 1 & 2. Top floor with private elevator is the penthouse condo. This 4 bedroom is very unique with a very open floor plan and high ceilings. The kitchen has huge workable island, wine fridge, built in oven and microwave, 6 burner gas top with grilling area. A separate full

    toyia Youtzy JENNETTE PROPERTIES, INC.

    1345 2nd St Unit C, Sarasota, FL 34236
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /22

    $1,500 per month

    • 2 Beds
    • 2 Baths
    • 1,353 Sq Ft
    • House for Rent

    Unlisted Address

    RATE IS ALL INCLUSIVE FOR A WEEKLY RENTAL! 5 minutes to Siesta Key Beach. Short walk to the HEATED pool, spa, and clubhouse! This very well appointed and updated 2/2 villa will be your slice of paradise! Both bedrooms have queen beds. Split bedroom floor plan. Huge master bedroom closet. Separate vanity area in master bath. ZERO carpet! Updated kitchen with granite counters! Eat in kitchen as

    Christina Johnson WHITE SANDS PARADISE REALTY

    Unlisted Address
  • 1709 Pelican Cove Rd Unit GL349, Sarasota, FL 34231
    1709 Pelican Cove Rd Unit GL349, Sarasota, FL 34231
    1709 Pelican Cove Rd Unit GL349, Sarasota, FL 34231
    /29

    $1,800 per month

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

    1709 Pelican Cove Rd Unit GL349, Sarasota, FL 34231

    ***AVAILABLE NOW THROUGH NOVEMBER 30, 2025. Ready to escape the winter, come to Pelican Cove located in South Sarasota! One bedroom one bathroom fully furnished. Steps to one of 6 pools. First floor condo with screened-in lanai that views nature's splendor right outside your patio door! Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    1709 Pelican Cove Rd Unit GL349, Sarasota, FL 34231
  • 1720 Glenhouse Dr Unit GL427, Sarasota, FL 34231
    1720 Glenhouse Dr Unit GL427, Sarasota, FL 34231
    1720 Glenhouse Dr Unit GL427, Sarasota, FL 34231
    /40

    $2,200 per month

    • 2 Beds
    • 2 Baths
    • 1,330 Sq Ft
    • Condo for Rent

    1720 Glenhouse Dr Unit GL427, Sarasota, FL 34231

    AVAILABLE SEPTEMBER 2025. This is a second-floor condominium, 2 bedroom 2 bathroom. Wait 'til you see you the condo. Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include an 86-slip boat harbor with sailboat water, excellent rates, and a launch dock for kayaks and canoes, 6 heated

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    1720 Glenhouse Dr Unit GL427, Sarasota, FL 34231
  • 1359 Glendale Cir W Unit 214, Sarasota, FL 34232
    1359 Glendale Cir W Unit 214, Sarasota, FL 34232
    1359 Glendale Cir W Unit 214, Sarasota, FL 34232
    /28

    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 992 Sq Ft
    • Apartment for Rent

    1359 Glendale Cir W Unit 214, Sarasota, FL 34232

    Your vacation rental is ready for you. This two bedroom Villa is located in the desirable and active 55 plus community of Forest Pines. Updated throughout with granite counters in kitchen and baths, spa like showers in both bathrooms, tile plank flooring through out the unit, A lovely updated Florida room with greenbelt views which is perfect for your morning cup of coffee. Forest Pines offers ,

    toyia Youtzy JENNETTE PROPERTIES, INC.

    1359 Glendale Cir W Unit 214, Sarasota, FL 34232
  • 770 S Palm Ave Unit 1001, Sarasota, FL 34236
    770 S Palm Ave Unit 1001, Sarasota, FL 34236
    770 S Palm Ave Unit 1001, Sarasota, FL 34236
    /36

    $5,500 per month

    • 2 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Condo for Rent

    770 S Palm Ave Unit 1001, Sarasota, FL 34236

    Stunning furnished rental available for long term occupancy. High-end furnishings, luxury finishes and a Million dollar view. Iconic building offering an exceptional downtown lifestyle. It’s located on Marina Row with the best view of every coveted sight in Sarasota: the open bay, moored sailboats along Bayfront Park, the John Ringling Bridge, Golden Gate Point, Bird Key, Lido Key, Siesta Key,

    Tammy Garner COLDWELL BANKER REALTY

    770 S Palm Ave Unit 1001, Sarasota, FL 34236
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /58

    $8,500 per month

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • House for Rent

    Unlisted Address

    Welcome to the "Hangout on Hyde" where comfort, privacy & fun collide! We are a fully renovated, turnkey furnished, beach inspired, 3 bedroom 2 bath heated saltwater pool home w/ outdoor kitchen located just 2 miles from Siesta Key in the Arlington Park neighborhood. We are a pet friendly home with a fully fenced backyard and private screen enclosed lanai allowing you to enjoy meals outside at

    Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

    Unlisted Address
  • 212 Cosmopolitan Ct, Sarasota, FL 34236
    212 Cosmopolitan Ct, Sarasota, FL 34236
    212 Cosmopolitan Ct, Sarasota, FL 34236
    /28

    $4,500 per month

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • House for Rent

    212 Cosmopolitan Ct, Sarasota, FL 34236

    DOWNTOWN SARASOTA Annual rental FURNISHED. 2BR + loft downtown townhouse. Owner provides streaming service. Reimburse Owner 70/mo for WI-FI; Tenant responsible for electric and water. The Q defines LUXURY & QUALITY with a DOWNTOWN LIFESTYLE in an intimate 40 home community. Superbly planned & designed in a premier location, the Q is one block to Main Street - walk to shopping, restaurants,

    Margaret Young JENNETTE PROPERTIES, INC.

    212 Cosmopolitan Ct, Sarasota, FL 34236
  • 1064 N Tamiami Trail Unit 1627, Sarasota, FL 34236
    1064 N Tamiami Trail Unit 1627, Sarasota, FL 34236
    1064 N Tamiami Trail Unit 1627, Sarasota, FL 34236
    /97

    $3,250 per month

    • 2 Beds
    • 2 Baths
    • 1,084 Sq Ft
    • Condo for Rent

    1064 N Tamiami Trail Unit 1627, Sarasota, FL 34236

    DOWNTOWN CONDO IN BROADWAY PROMENADE! NOW AVAILABLE FOR ANNUAL RENTAL, “Turnkey Furnished” 2 bedrooms/2 baths, located on the top floor of the highly sought after Broadway Promenade. As you enter the unit, you are greeted by a bright and open living and dining room, beautifully furnished with leather furniture, a wooden TV Stand/Console with Electric Fireplace and Crystal Insert | Multi-Color LED

    Chrissie Cummings JENNETTE PROPERTIES INC

    1064 N Tamiami Trail Unit 1627, Sarasota, FL 34236
  • 1116 Westway Dr, Sarasota, FL 34236
    1116 Westway Dr, Sarasota, FL 34236
    1116 Westway Dr, Sarasota, FL 34236
    /80

    $5,800 per month

    • 3 Beds
    • 3 Baths
    • 1,516 Sq Ft
    • House for Rent

    1116 Westway Dr, Sarasota, FL 34236

    The Lido Shores Mango Retreat. This stylish home is located in the heart of Lido Shores, just steps to the beautiful private white sand beaches and crystal blue waters of the Gulf of Mexico. Canopied by a lush mango tree, with a tranquil and tropical setting. Features, 3/3, 1 car garage, screened lanai & office. From the bright entry is a spacious dining room with an open-concept kitchen with

    Valarie Wadsworth MICHAEL SAUNDERS & COMPANY

    1116 Westway Dr, Sarasota, FL 34236
  • 3801 Helene St, Sarasota, FL 34233
    3801 Helene St, Sarasota, FL 34233
    3801 Helene St, Sarasota, FL 34233
    /37

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    3801 Helene St, Sarasota, FL 34233

    Captivating Pool Home in an Ideal Location: This enchanting residence boasts 3 bedrooms, 2 bathrooms, and a beautiful in-ground pool. Situated in a prime location, it provides convenient access to nearby beaches and popular attractions. Available May-December for $4,000/month 2025. Booked for through April of 2025. Available Jan - April for $7500/month through 2026.

    Philip Pisano, III MICHAEL SAUNDERS & COMPANY

    3801 Helene St, Sarasota, FL 34233
  • 2159 Constitution Blvd, Sarasota, FL 34231
    2159 Constitution Blvd, Sarasota, FL 34231
    2159 Constitution Blvd, Sarasota, FL 34231
    /39

    $4,495 per month

    • 3 Beds
    • 3 Baths
    • 2,752 Sq Ft
    • House for Rent

    2159 Constitution Blvd, Sarasota, FL 34231

    Monthly Furnished Pool & Dock House - Welcome to this spacious, fully furnished home situated on an expansive 20,000 sq ft waterfront lot, complete with a boat lift. This turn-key property features: 3 Bedrooms: Each bedroom boasts a king-size bed, private bathroom access, and ample closet space. Screened-in Lanai: Enjoy breathtaking views of the backyard and its amenities, including a deep heated

    Michael Sorensen STRINGER MANAGEMENT INC

    2159 Constitution Blvd, Sarasota, FL 34231
  • 1770 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    1770 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    1770 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    /32

    $4,495 per month

    • 3 Beds
    • 2 Baths
    • 1,207 Sq Ft
    • Condo for Rent

    1770 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236

    Luxurious Condo Steps from Private Beach on Lido Key - Welcome to your dream rental in the prestigious Lido Harbour Towers! This exquisite 3-bedroom, 2-bathroom condo offers 1200 sq ft of elegantly appointed living space, with an additional 700 sq ft of expansive terraces for seamless indoor-outdoor living. Prime Location: Just steps from your private beach on Lido Key, perfect for sunbathing,

    Michael Sorensen STRINGER MANAGEMENT INC

    1770 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
  • 9062 Midnight Pass Rd Unit 7, Sarasota, FL 34242
    9062 Midnight Pass Rd Unit 7, Sarasota, FL 34242
    9062 Midnight Pass Rd Unit 7, Sarasota, FL 34242
    /27

    $7,900 per month

    • 2 Beds
    • 2 Baths
    • 1,251 Sq Ft
    • Condo for Rent

    9062 Midnight Pass Rd Unit 7, Sarasota, FL 34242

    Bring your BOAT! this lovely and well-appointed condo sits directly on Blind Pass with a view of the Gulf of Mexico and has private boat dock for guests and owners. Completely updated with a beautiful large kitchen and stylish furnishings throughout. Primary bedroom has king bed and access to covered lanai/patio. Guest room features two double beds, Bathrooms are updated and brand-new washer and

    Robin Turner WATERSIDE REALTY LLC

    9062 Midnight Pass Rd Unit 7, Sarasota, FL 34242
  • 1350 N Portofino Dr Unit 207, Sarasota, FL 34242
    1350 N Portofino Dr Unit 207, Sarasota, FL 34242
    1350 N Portofino Dr Unit 207, Sarasota, FL 34242
    /36

    $2,300 per month

    • 1 Bed
    • 2 Baths
    • 780 Sq Ft
    • Condo for Rent

    1350 N Portofino Dr Unit 207, Sarasota, FL 34242

    This stunning one-bedroom, two-bathroom condo in Siesta Harbor in the Tarpon Building is the perfect combination of luxury, convenience, and breathtaking views. Located in a prime location, boating access, canal frontage, and mesmerizing Intracoastal Waterway views. Step inside and be captivated by the modern elegance of this home. The kitchen is a chef's dream, featuring stainless steel

    Judith Guzzi JUDITH GUZZI & ASSOCIATES LLC

    1350 N Portofino Dr Unit 207, Sarasota, FL 34242
  • 8625 Midnight Pass Rd Unit B508, Sarasota, FL 34242
    8625 Midnight Pass Rd Unit B508, Sarasota, FL 34242
    8625 Midnight Pass Rd Unit B508, Sarasota, FL 34242
    /58

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Condo for Rent

    8625 Midnight Pass Rd Unit B508, Sarasota, FL 34242

    ***In season minimum 30 day lease, $4,000.00/month***Siesta Key 2 Bed 2 Bath rental. Breathtaking Bay and Gulf views from this stunning fifth floor, end residence. Located in sought-after Siesta Key, close to shopping, restaurants and the nation's number one beach, Siesta Key Beach. Relax and enjoy views across a sparkling pool to gorgeous Sarasota Bay from the privacy of your large balcony and

    Gene Burwood PARADISE PALMS REALTY GROUP

    8625 Midnight Pass Rd Unit B508, Sarasota, FL 34242
  • 1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
    1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
    1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
    /56

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,840 Sq Ft
    • Condo for Rent

    1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242

    Enjoy one of the best views on Siesta Key ~ unobstructed WATER VIEWS of the Bay/Intercoastal from your private large covered lanai with all new impact glass doors, and have coffee on your own private brick patio with water views that leads right out to the dock. This seasonal rental is available MAY 1, 2025, but this unit does have a 3 month minimum stay. This spacious unit is one of Siesta Key's

    Tony Andrews ANDREWS & ASSOCIATES REALTY

    1280 Dolphin Bay Way Unit 204, Sarasota, FL 34242
  • 1720 Glenhouse Dr Unit GL429, Sarasota, FL 34231
    1720 Glenhouse Dr Unit GL429, Sarasota, FL 34231
    1720 Glenhouse Dr Unit GL429, Sarasota, FL 34231
    /34

    $1,750 per month

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

    1720 Glenhouse Dr Unit GL429, Sarasota, FL 34231

    ***AVAILABLE MAY 2026***. This is a second-floor condominium, 1 bedroom 1 bathroom with a pull-down murphy bed. Brand bathroom and shower. In addition, you have an updated kitchen. Wait to you see you the condo. Pelican Cove is a 75-acre gated, vibrant, waterfront community nestled among manicured tropical foliage truly offering something for everyone. Abundant amenities include an 86-slip

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    1720 Glenhouse Dr Unit GL429, Sarasota, FL 34231
  • 1647 Brookhouse Ct Unit BR246, Sarasota, FL 34231
    1647 Brookhouse Ct Unit BR246, Sarasota, FL 34231
    1647 Brookhouse Ct Unit BR246, Sarasota, FL 34231
    /27

    $1,995 per month

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

    1647 Brookhouse Ct Unit BR246, Sarasota, FL 34231

    Step into the relaxed elegance of Pelican Cove with this fully furnished second-floor condo, available for the 2026 season at $3,00 per month. This light-filled 1-bedroom, 1-bath unit offers a peaceful retreat within one of Sarasota’s most sought-after gated communities. Set on 78 acres of lush, tropical landscape, Pelican Cove features resort-style amenities including multiple pools, tennis

    Heidi Thompson STRINGER MANAGEMENT INC

    1647 Brookhouse Ct Unit BR246, Sarasota, FL 34231
  • 5620 Ashton Lake Dr Unit 5620, Sarasota, FL 34231
    5620 Ashton Lake Dr Unit 5620, Sarasota, FL 34231
    5620 Ashton Lake Dr Unit 5620, Sarasota, FL 34231
    /24

    $2,295 per month

    • 2 Beds
    • 2 Baths
    • 1,233 Sq Ft
    • Condo for Rent

    5620 Ashton Lake Dr Unit 5620, Sarasota, FL 34231

    Welcome to your perfect seasonal retreat just 3.5 miles from the powdery white sands of Siesta Key Beach. This beautifully furnished 2-bedroom, 2-bathroom home with a den comfortably sleeps up to six guests and is available for the 2026 season at $3,500 per month. The attached one-car garage is stocked with everything you need for a beach day, making it easy to enjoy the nearby coast. Located in

    Heidi Thompson STRINGER MANAGEMENT INC

    5620 Ashton Lake Dr Unit 5620, Sarasota, FL 34231
  • 1626 Brookhouse Dr Unit BR137, Sarasota, FL 34231
    1626 Brookhouse Dr Unit BR137, Sarasota, FL 34231
    1626 Brookhouse Dr Unit BR137, Sarasota, FL 34231
    /24

    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,283 Sq Ft
    • Condo for Rent

    1626 Brookhouse Dr Unit BR137, Sarasota, FL 34231

    ***AVAILABLE April 11, 2026*** MINIMUM 2 MONTH RENTAL. BEAUTIFUL 1ST FLOOR UNIT, 2 BEDROOM 2 BATH plus den. IN HIGHLY SOUGHT AFTER PELICAN COVE. Rental rates fluctuate for seasonal rates and off-season rates. December through April, season rates apply. Come live in the Florida Lifestyle! This 75-acre gated waterfront community has it all. Pelican Cove has 6 heated pools, 4 lighted tennis

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    1626 Brookhouse Dr Unit BR137, Sarasota, FL 34231
  • 1649 Stanford Ln, Sarasota, FL 34231
    1649 Stanford Ln, Sarasota, FL 34231
    1649 Stanford Ln, Sarasota, FL 34231
    /17

    $7,500 per month

    • 3 Beds
    • 2 Baths
    • 1,995 Sq Ft
    • House for Rent

    1649 Stanford Ln, Sarasota, FL 34231

    No damage from Hurricane Helene or Milton! Available for seasonal and annual rental 2025, call agent for pricing. Discover the epitome of waterfront living in this exquisite 3-bedroom, 2-bathroom home located in Sarasota, Florida. Set on over a quarter-acre of prime land, this beautiful residence features a spacious 1,995 square foot open floor plan that leads to your private pool, ideal for

    Rinat Sikdar COLDWELL BANKER REALTY

    1649 Stanford Ln, Sarasota, FL 34231
  • 1865 Orchid St, Sarasota, FL 34239
    1865 Orchid St, Sarasota, FL 34239
    1865 Orchid St, Sarasota, FL 34239
    /29

    $10,000 per month

    • 4 Beds
    • 3 Baths
    • 2,252 Sq Ft
    • House for Rent

    1865 Orchid St, Sarasota, FL 34239

    Welcome to Tropical Paradise! This stunning, fully renovated home away from home is in a prime location, West of Trail. Take a dip in the private heated pool, sip cocktails at the tiki bar, and soak up the Florida sun. With spacious bedrooms, a fully equipped kitchen, and cozy living areas, you'll have everything you need for a comfortable stay. Located five minutes to downtown Sarasota and ten

    Tina Ellis COMPASS FLORIDA LLC

    1865 Orchid St, Sarasota, FL 34239
  • 1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
    1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
    1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
    /40

    $11,000 per month

    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    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

    1304 Siesta Bayside Dr Unit 1304B, Sarasota, FL 34242
  • 2569 Prospect St, Sarasota, FL 34239
    2569 Prospect St, Sarasota, FL 34239
    2569 Prospect St, Sarasota, FL 34239
    /51

    $12,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,241 Sq Ft
    • House for Rent

    2569 Prospect St, Sarasota, FL 34239

    Welcome to Luxe Arlington Park Home! Step into this exquisite and impeccably maintained abode, nestled in the heart of two of Sarasota's most charming and time-honored neighborhoods. The Arlington Park/Rustic Lodge enclave seamlessly blends the perks of urban living with the warmth of a close-knit community. Enjoy strolls or bike rides to the beloved Arlington Park, a haven for families and pets

    Andy Moore GULF COAST REALTY & MANAGEMENT

    2569 Prospect St, Sarasota, FL 34239
  • 5216 Calle de Costa Rica, Sarasota, FL 34242
    5216 Calle de Costa Rica, Sarasota, FL 34242
    5216 Calle de Costa Rica, 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
  • 306 Beach Rd Unit 306, Sarasota, FL 34242
    306 Beach Rd Unit 306, Sarasota, FL 34242
    306 Beach Rd Unit 306, Sarasota, FL 34242
    /48

    $13,200 per month

    • 3 Beds
    • 2.5 Baths
    • 2,041 Sq Ft
    • Condo for Rent

    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

    306 Beach Rd Unit 306, Sarasota, FL 34242
  • 5640 Cape Leyte Dr, Sarasota, FL 34242
    5640 Cape Leyte Dr, Sarasota, FL 34242
    5640 Cape Leyte Dr, 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
  • 2121 Pueblo Cir Unit V6, Sarasota, FL 34231
    2121 Pueblo Cir Unit V6, Sarasota, FL 34231
    2121 Pueblo Cir Unit V6, Sarasota, FL 34231
    /14

    $2,200 per month

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

    2121 Pueblo Cir Unit V6, Sarasota, FL 34231

    In Gulf Gate area,55+ community of Wooside Village West, annual rental, quiet & well maintained , 2b/2b villa, open floor plan & tile thru out. Renovated with new kitchen cabinets, granite counters, newest appliances. Baths remodeled with cabinets, granite counters, walk-in closet,new lighting ,unit painted. Brand new A/C system just been replaced. End unit with open patio in the back, greenview

    Lydia Perignon FINE PROPERTIES

    2121 Pueblo Cir Unit V6, Sarasota, FL 34231
  • 5577 Contento Dr, Sarasota, FL 34242
    5577 Contento Dr, Sarasota, FL 34242
    5577 Contento 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
  • 116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
    116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
    /66

    $7,500 per month

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

    116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242

    An Ascendia Property! **Listing reflects monthly rate. Unit can be rented on a 1-Week minimum basis - call us today for weekly pricing!** Welcome to your BOHO CHIC beach retreat located near the famous Crescent Beach on Siesta Key! You'll feel right at home when you stay in this 2 bedroom, 2 bathroom (sleeps 5) condo. Spend time cooking your favorite meals in the fully stocked kitchen... Cozy up

    Beth Dilley ASCENDIA REAL ESTATE

    116 Vista Hermosa Cir Unit 308, Sarasota, FL 34242
  • 50 Central Ave Unit 16A, Sarasota, FL 34236
    50 Central Ave Unit 16A, Sarasota, FL 34236
    50 Central Ave Unit 16A, Sarasota, FL 34236
    /44

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,595 Sq Ft
    • Condo for Rent

    50 Central Ave Unit 16A, Sarasota, FL 34236

    Discover the epitome of luxury and convenience with our exclusive rental opportunity in Sarasota, available May through December. Nestled on the corner of Main St and Central Ave, this contemporary corner unit sits on the 16th floor, just one level below the penthouse. Immerse yourself in the vibrancy of downtown Sarasota, where the finest amenities and attractions are merely steps away. This

    Henry Rossi RENT SARASOTA

    50 Central Ave Unit 16A, Sarasota, FL 34236
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /89

    $10,000 per month

    • 4 Beds
    • 3 Baths
    • 2,445 Sq Ft
    • House for Rent

    Unlisted Address

    Welcome to the Ringling Retreat, a luxurious family compound in the heart of downtown Sarasota. The property sits just a few blocks from the East end of Main Street downtown and is perfectly walkable to the Legacy Trail, Payne Park, & a number of shops & restaurants. A screened entryway in the front greets you before stepping through the front door into a light and bright living area with views

    Adam Kabinoff UPTOP REAL ESTATE SERVICES, LLC

    Unlisted Address
  • 7205 Curtiss Ave Unit 2F, Sarasota, FL 34231
    7205 Curtiss Ave Unit 2F, Sarasota, FL 34231
    7205 Curtiss Ave Unit 2F, Sarasota, FL 34231
    /18

    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft
    • Condo for Rent

    7205 Curtiss Ave Unit 2F, Sarasota, FL 34231

    A charming two-bedroom condominium conveniently located near Siesta Key beach awaits you. Each bedroom boasts a comfortable queen-size bed for a restful night's sleep, complemented by TVs in both rooms for your entertainment. This unit features an indoor laundry room for added convenience, along with a screened-in lanai where you can unwind. Additionally, the eat-in kitchen provides a cozy space

    Maureen Plichta STRINGER MANAGEMENT INC

    7205 Curtiss Ave Unit 2F, Sarasota, FL 34231
  • 5555 Ashton Way Unit 5555, Sarasota, FL 34231
    5555 Ashton Way Unit 5555, Sarasota, FL 34231
    5555 Ashton Way Unit 5555, Sarasota, FL 34231
    /54

    $3,600 per month

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Condo for Rent

    5555 Ashton Way Unit 5555, Sarasota, FL 34231

    Unit available to rent August 2025- Dec 20, 2025. Rented Jan- March 2026. Available to rent April 2026 onwards. Only 3.5 miles to the world-famous sugary sands of Siesta Key Beach. Enjoy the Gulf of Mexico. Close to I-75, rte. 41, shops, restaurants, schools and hospitals. We are also connected by a foot bridge to Merchants Mart shopping center consisting of CVS, ACE hardware, take-outs, liquor

    Philip Abraham ASHTON LAKES REALTY INC

    5555 Ashton Way Unit 5555, Sarasota, FL 34231
  • 2908 Captiva Dr, Sarasota, FL 34231
    2908 Captiva Dr, Sarasota, FL 34231
    2908 Captiva Dr, Sarasota, FL 34231
    /12

    $6,000 per month

    • 4 Beds
    • 2 Baths
    • 1,781 Sq Ft
    • House for Rent

    2908 Captiva Dr, Sarasota, FL 34231

    RENTED JAN., FEB., MARCH 2025, AVAILABLE MAY THROUGH DEC. AT OFF-SEASON RATES. A perfect vacation getaway in prime Golf Gate location. Bring the family to this 4 bedroom, 2 bath home with a private sparkling pool under a screened cage. The home offers 4 bedrooms, a large open living room and dining area with beautiful new flooring. The family room is off the kitchen and has sliding glass

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

    2908 Captiva Dr, Sarasota, FL 34231
  • 425 Mckinley Dr, Sarasota, FL 34236
    425 Mckinley Dr, Sarasota, FL 34236
    425 Mckinley Dr, Sarasota, FL 34236
    /81

    $9,590 per month

    • 4 Beds
    • 4 Baths
    • 2,440 Sq Ft
    • House for Rent

    425 Mckinley Dr, Sarasota, FL 34236

    The prices listed are PER WEEK rates...7 day Min... Walk to the Beach, 10 min to St Armand’s Circle! Lido Key Family HomeNestled quietly on the peaceful corner of McKinley Drive and The Boulevard of Presidents, “The Green House” awaits its next guests, patiently anticipating the perfect family ready for an escape to the beach! “The Green House” decorated and furnished by an interior designerno

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    425 Mckinley Dr, Sarasota, FL 34236
  • 446 Canal Rd Unit 5, Sarasota, FL 34242
    446 Canal Rd Unit 5, Sarasota, FL 34242
    446 Canal Rd Unit 5, Sarasota, FL 34242
    /52

    $6,500 per month

    • 2 Beds
    • 1 Bath
    • 680 Sq Ft
    • Condo for Rent

    446 Canal Rd Unit 5, Sarasota, FL 34242

    You will be charmed by how vibrant and quaint this midcentury ground floor condo is... from the lime green exterior, to the pink hibiscus bushes blooming around the turquoise pool, which is nestled behind the privacy of a fence and garden surrounding the property! THE BEST PART ABOUT THIS UNIT... the Keylime Retreat is a 5 minute walk to the pure white sands of Siesta Beach, and an 8 minute walk

    Beth Dilley ASCENDIA REAL ESTATE

    446 Canal Rd Unit 5, Sarasota, FL 34242

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