Sarasota's Premier Homes

5577 CONTENTO DRIVE

SARASOTA , FL 34242

MLS#: A4607468

$5,000

Status: Active
Listing number: A4607468
Listing provided by: ASCENDIA REAL ESTATE
Listing agent phone: None
Last update: a month ago
On site: 1 year, 6 months ago
Browse Properties
SIESTA ISLES - Residential Lease

Property

Beds

2

Full Baths

2

1/2 Baths

None

Year Built

1969

Sq.Footage

1,424

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 designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world-famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.

Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Open Floorplan, Walk-In Closet(s)

  • Total Bedrooms

    2

  • Bathrooms

    2

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Heating YN

    YES

  • Heating

    Central, Electric

  • Pet friendly

    Breed Restrictions, Number Limit, Size Limit, Yes

Exterior

  • Garage

    No

  • Parking

    Driveway

  • Pool

    Yes

  • Pool Features

    In Ground, Private

  • Waterfront YN

    YES

  • View

    Canal, Water

Area & Lot

  • Lot Features

    Waterfront

  • Lot Size(acres)

    0.26

  • Property Type

    Residential Lease

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $5,000

  • Sq. Footage

    1, 424

  • Price/SqFt

    $3

HOA

  • Association

    NO

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Senior Community YN

    NO

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Sarasota

Elementary School

Middle School

High School

Listing Courtesy of Beth Dilley , ASCENDIA REAL ESTATE

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent MichaelGraf

Business Coach | Executive Sales Associate | Realtor®

MichaelGraf

Call Michael today to schedule a private showing.

(941) 315-6980

michael@thegrafgroupvip.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
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 designed interior with thoughtful updates throughout, from the brand-new kitchen to the spa-like bathrooms. You'll find a designated office space off the kitchen, perfect for remote work. The first bedroom features a king bed, and the second bedroom features a queen bed. Outside, soak up the Florida sunshine by the sparkling saltwater pool. With direct canal access, cast a line for some fishing, or launch a paddle board and explore the tranquil canals, where you're likely to spot local manatees and other fascinating wildlife. After exploring the canals, take a leisurely walk of just a few minutes to the world-famous Siesta Key Beach. Feel the soft, powdery quartz sand between your toes and bask in the beauty of the Gulf. Then, it's back to your private oasis where, as the sun begins its descent, it's 'tini time! Mix your favorite martini and savor it while watching the spectacular sunset paint the sky over the canal, beautifully highlighting silhouetted palm trees. It's truly an unforgettable end to a perfect day! Bikini Tini Time offers the perfect blend of tranquility and convenience, just moments from Siesta Key Village's vibrant shops and restaurants. Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.

5577 CONTENTO DRIVE

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

New on site today
NEWER CONSTRUCTION WITH A PRIVATE POOL AND WATER VIEW! Enjoy Florida living at it's best in this White Star model built in 2022 in the highly desirable, resort-style Neal Community of Grand Park! As you enter your new oasis, you’ll be greeted with the bright and airy open floor plan and sliders that open out to the pool area with a relaxing lake view. The master suite features a tray ceiling, walk in shower, his and her separate closets, and a beautiful water view to wake up to. With 3 bedrooms, 2 1/2 bathrooms, and a den that can easily be used as a 4th bedroom, there is plenty of room for the family. The screened in pool area boasts a large covered space for grilling and entertaining. The Grand Park amenity center offers resort style living which includes two pools, fitness center, pickleball courts, tennis courts, manicured trails for walking/running, playground, dog park, and more! And on top of it all, this is in one of the best school districts! Annual lease. First month, security, and last month to move in. Lawn and pool maintenance included. Tenant is responsible for utilities. Credit check and HOA application required. (Included, but not pictured here - window treatments, ceiling fans/light fixtures in all rooms, washer/dryer, and refrigerator.)
#A4666736

SARASOTA

6636 FORT PIERCE AVENUE

3 Beds

2 Baths

2,846 Sq.Ft.

$4,000

MLS#: A4666736

New on site 1 day ago
AVAILABLE SHORT TERM or LONG TERM. Discover the charm of this 3 bedroom, 2 bathroom home with ceramic tile flooring throughout and a laundry room with clothes washer and dryer. 3039 Chase Circle is nestled in the heart of Gulf Gate in Sarasota, Florida just 2.4 Miles to the BEACH. This inviting cheerful residence offers a sunny, harmonious blend of comfort and convenience, making it an ideal choice for those seeking a vibrant yet tranquil living experience. Two car attached garage. Property has washer and dryer. Situated in the Gulf Gate Estates neighborhood, residents appreciate the area's dog-friendly atmosphere, well-maintained yards with mature palm trees and gardens, and easy access to grocery stores and restaurants and the #1 rated best beach Siesta Key Beach. Just minutes away, you'll find the world-renowned Siesta Key Beach, celebrated for its pristine sands and clear waters. For shopping and dining enthusiasts, St. Armands Circle offers a variety of boutiques and eateries. Nature lovers can explore the nearby Myakka River State Park, perfect for hiking and wildlife observation. Embrace the opportunity for 3039 Chase Circle, where the best of Sarasota's amenities are within your reach.
#A4669035

SARASOTA

3039 CHASE CIRCLE

3 Beds

2 Baths

2,329 Sq.Ft.

$5,000

MLS#: A4669035

New on site 1 day ago
AVAILABLE DEC. 2025, JAN., FEB., MARCH, APRIL 2026 and off-season. VACATION IN STYLE IN THIS 3-BEDROOM GROUND FLOOR TOTALLY UPDATED UNIT AT PINESTONE. Quartz countertops in kitchen, new cabinets, new appliances, all new furniture throughout, smart TVs, new carpet in the living room and bedrooms, and a new washer and dryer. Lots of natural light lend to the bright and cheerful atmosphere in this well-furnished and tastefully decorated condo. The glassed and newly screened lanai gives that added year-round space, and they have added new outside patio space. They have thought of everything. This is the perfect vacation condo decorated in a coastal theme, offering everything you would need for a few months in the sunshine. Pinestone is an amenity-rich community featuring a huge heated pool, a 32-seat movie theater, a gathering room, a fitness center, a billiards room, a card room, two lighted tennis/pickleball courts, a firepit area, and much more. The Legacy trail access is a short distance from the community and it is less than 15 minutes to the sugar sandy beaches of Siesta Key. You can be downtown Sarasota in less than 25 minutes to enjoy the many restaurants, performing arts, the Ringling Museum of Arts, and many more cultural experiences.
#A4669140

SARASOTA

8369 WINGATE DRIVE 2114

3 Beds

2 Baths

1,405 Sq.Ft.

$5,000

MLS#: A4669140

New on site 2 days ago
Peak Season Rates are $4700/month. Discover your perfect seasonal retreat in this stunning three-bedroom, two-bathroom condo nestled within the sought after gated community of Botanica. This exceptional Sandlewood model spans nearly 2,000 square feet and features a coveted split floor plan that thoughtfully separates the primary bedroom from the secondary bedrooms, creating an ideal balance of togetherness and privacy. Step inside to find soaring ceilings that create an open, airy atmosphere throughout the home, while abundant natural light streams through the windows of this desirable end unit. The second-floor location offers peaceful lake and fountain views, providing a serene backdrop for your morning coffee or evening relaxation. The well-appointed interior showcases quality finishes and thoughtful design elements that make daily living a pleasure. Two dedicated driveway parking spaces ensure convenience, with additional guest parking nearby for when friends and family visit. Botanica's resort-style amenities truly shine, featuring two heated swimming pools, a 4,000-square-foot clubhouse, fitness center, library, and various social spaces perfect for meeting neighbors. The community's culinary kitchen and grilling areas provide wonderful opportunities for entertaining and socializing. Location couldn't be more convenient, with shopping destinations just minutes away and the world-renowned Siesta Beach accessible within thirty minutes. Downtown Sarasota's vibrant arts scene, exceptional restaurants, and charming boutiques are equally close, offering endless entertainment options. This seasonal rental requires a minimum three-month commitment and represents an outstanding opportunity to experience the best of Florida living in one of Palmer Ranch's most sought-after communities. Your slice of paradise awaits in this remarkable condo that perfectly balances luxury, comfort, and convenience.
#A4669346

SARASOTA

5290 DESCANSO COURT 201B19

3 Beds

2 Baths

2,364 Sq.Ft.

$4,700

MLS#: A4669346

New on site 3 days ago
Seasonal/ short term rental Beautifully remodeled private and tranquil home on large fenced lot in Sarasota very close to the north end of Siesta Key. This home is flooded with natural sunlight from abundant windows through this open floor plan. The kitchen is spacious with solid wooden cabinetry topped with slab granite counters with breakfast bar, custom tile backsplash and stainless steel appliances. The dining table seats eight people easily with additional seating for 4 at the counter. The furniture is stylish, modern, sleek and comfortable. This property is pet friendly (no aggressive breed allowed). If you want a wonderful base camp for your next vacation, this is it. You will find yourself close to Siesta Key beach, the #1 rated beach in the country. This home is also convenient to shopping, casual and fine dining, downtown Sarasota, museums, the theater and opera. CALL now for your turn in the Florida sunshine!
#A4669275

SARASOTA

3932 SUNSHINE AVENUE

2 Beds

1 Baths

1,300 Sq.Ft.

$4,800

MLS#: A4669275

New on site 3 days ago
This is a must see Executive home in a gated community. As you walk through the double doors of this 3000 plus square foot home you see the patio and pool area calling for you to relax! This open floor plan offers so much.. kitchen & living room for visiting and entertaining to playing a round of pool all in the same area. Home has 4 bedrooms & 3 baths PLUS a den/fitness room. You can serve dinner in the formal dinning room and have breakfast or lunch in the eat in kitchen, my preference would be the large patio area overlooking the pool & lake! Fishing is allowed for residents!! For your safety the home does have a security alarm system in place and will be activated for your use. This home is beautifully furnished and is available for an annual lease. Amenities include Clubhouse & Tennis Court. New 65” smart Samsung tv for the lounge.
#A4668726

SARASOTA

2933 SEASONS BOULEVARD

4 Beds

3 Baths

3,969 Sq.Ft.

$4,295

MLS#: A4668726

New on site 3 days ago
EXECUTIVE villa for LEASE in Palm Aire Golf and Country Club! A STUNNING RENOVATION of this TURNKEY FURNISHED oversized two bedroom / two bathroom plus den EXECUTIVE villa will be sure to impress you for your winter stay or longer! FABULOUS LIGHT AND BRIGHT SEASONAL FURNISHED RENTAL. Every room has designer tile, cabinetry and finishes, custom plantation shutters and woodwork. It features a solid wood cabinetry and premium granite in the chef's kitchen with stainless steel appliances, double wall ovens and a walk-in pantry. There are two beautiful custom bathrooms, multiple closets, inside laundry, premium fans and all custom closets. The primary bedroom features a stunning en suite bathroom, full wall of designer closets and large armoire. The primary bedroom flows into a sunny home office / den with another custom closet. The second bedroom also boasts a custom bath and an oversized professionally planned closet space. The large sunny Florida room connects seamlessly to the living area and overlooks a spectacular lake view. The 2 CAR garage boasts fresh paint, a wall of storage and another refrigerator. This community has 2 heated pools . Additionally you can join Palm Aire Golf and Country Club. Optional memberships at the club are available for seasonal or annual enjoyment. Palm Aire feature 36 holes of championship golf, tennis, pickleball, fitness, dinning and many clubs / groups. The villa is right in the heart of the University shopping, UTC mall, dining, recreation and entertainment districts. You will be a quick drive to all the shops, dining, fitness and cultural events along the University corridor and downtown Sarasota as well! Rent includes utilities.
#A4669088

SARASOTA

5455 GOLF POINTE DRIVE 5455

2 Beds

2 Baths

2,630 Sq.Ft.

$5,500

MLS#: A4669088

New on site 4 days ago
AVAILABLE FOR 2026 SEASON! Welcome to your Heatherwood Heaven on the Highland Golf course in The Beautiful Meadows! When you pull up to this amazing property, you will notice the meticulous maintained landscape in the front and back. This unit has THREE outdoor patios to enjoy the stunning views and beautiful fresh Florida air. Upon entering, you'll be captivated by the elegant interior, where every detail has been meticulously crafted to create an atmosphere of sophistication and comfort. The kitchen is immediately to the left and has everything you need to prepare a scrumptious meal. The glass sliding door in the kitchen opens to a verandah with bench seated dining where you can savor your morning coffee or dine al fresco with your family. Adjacent to the kitchen, you will find your indoor laundry room and a one car garage for your vehicle or storage. As you walk further down the unit, the spacious airy living and dining area is covered by gorgeous vinyl plank flooring, vaulted ceilings and luxurious furnishings to provide the perfect setting for relaxing evenings or entertaining guests, while enjoying the spectacular breathtaking views of the fairways and nature in your spacious screened in lanai. To the right will be your spacious primary bedroom providing a sanctuary for relaxation after a long day on the golf course. The bathroom offers his and hers closets, double vanity sink and walk in shower. It is here where you will again be able to go out to a little paved outdoor patio with colorful landscape to overlook the spectacular views of the Highland golf course. Upstairs, you'll find the two bedrooms, each offering a tranquil retreat for rest and rejuvenation. They share a bathroom with a walk in shower. This home is truly Paradise!! As a resident of The Meadows community, you'll enjoy access to an array of world-class amenities, including championship golf courses, pickleball courts, a Junior Olympic swimming pools, 5,000 square foot fitness center, walking trails, and clubhouse facilities. You are within walking distance to The Meadows Village where you will find many shops for your convenience. This community ensures endless opportunities for recreation and leisure. Your Heatherwood Heaven is conveniently located very near I-75, UTC shopping, Nathan Benderson Park, dining, top-rated schools, our famous beaches, Lakewood Ranch and the Sarasota-Bradenton Airport. This property is available for up to an 8 month lease and includes all utilities. Contact us today to schedule a private tour and embark on a lifestyle of unparalleled elegance in a golf course community.
#A4669118

SARASOTA

3141 HEATHERWOOD LANE

3 Beds

2 Baths

2,336 Sq.Ft.

$4,000

MLS#: A4669118

New on site 4 days ago
A must-see luxury rental that perfectly combines comfort, style, and privacy—ready for you to move right in and enjoy Sarasota living at its best. Live the Sarasota lifestyle in this beautifully furnished 2-bedroom, 2-bath courtyard villa located in the highly desirable Glen Oaks Manor. Step inside and fall in love with the bright, open floor plan, designer furnishings, and gourmet kitchen featuring high-end appliances and everything you need to feel right at home. Natural light pours through every room, highlighting the stylish details and spacious layout that make this villa a true retreat. Enjoy your own private courtyard oasis featuring a heated pool, outdoor TV, and plenty of space to relax or entertain. Set in a peaceful, tree-lined community with walking paths, this villa offers easy access to downtown Sarasota, shopping, dining, and the area’s award-winning beaches.
#A4668673

SARASOTA

3694 GLEN OAKS MANOR DRIVE

2 Beds

2 Baths

2,450 Sq.Ft.

$4,500

MLS#: A4668673

Vacation / Seasonal Rental $4,000 a month. WOW! A BEAUTIFUL UPSCALE VILLA just two miles to world famous SIESTA KEY BEACH. Woodside Village West is in the sought after Gulf Gate area offering trendy restaurants and shops. This 2 bedroom 2 bath has been totally remodeled with an open floor plan. As you enter you will see lite tile floors that look like wood throughtout. Wide open kitchen with stainless steel appliances, drop-down stainless hood, granite countertops and a breakfast bar with stools great for entertaining. Living room is open to the kitchen and has a large smart TV and Wi-Fi there are windows in every room with plantation shutters that give a wonderful light, bright and airy feel, This villa has been professionally decorated with chic, upscale furnishings. Step into the primary bedroom with beautiful queen bed that has four pillows and hotel style sheets. The en suite bathroom has a large shower, large walk-in closet, double vanities, granite countertops. The cozy second bedroom has a queen bed, two nightstands and closets. Second bathroom has a combination, tub, shower, beautiful tile and granite countertop. There is a lot of storage in this unit. The windows have been replaced with impact windows and The roof was replaced this year. Also a washer and dryer in the unit. There is assigned parking right by your front door with plenty of guest parking. The Community pool. HOA requires $150.00 application fee. 50% down at time of booking balance due Nov 1,2025. Must lease for 3 months at a time. Effective date Dec 1,2025 through May 1, 2026
#A4668173

SARASOTA

2181 PUEBLO CIRCLE V21

2 Beds

2 Baths

1,009 Sq.Ft.

$4,000

MLS#: A4668173

Rental Inquiry

Rental Inquiry

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here