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Are you looking for a sunny getaway? Our monthly rentals in Sarasota, Florida, offer the perfect escape. Whether you're seeking a winter retreat or a long-term stay, Sarasota has it all. From stunning beaches to vibrant cultural scenes, there’s something for everyone.
Distance to beach: 0.5 miles to Siesta Key Crescent Beach Access 12
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About this property
This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right...
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Charming Coastal Retreat Near Siesta Key Welcome to your Sarasota getaway! This bright and airy 3-bedroom, 2-bath home is perfectly located near the south bridge to Siesta Key, offering easy access to one of Florida’s most beautiful beaches.Property Highlights - Open-Concept Living: Sun-filled...
Featured review
We stayed here for 4 1/2 weeks starting 3-1-25. Very clean and probably one of the best stocked vacation rentals we’ve ever used. It didn’t have a pool, but we knew that going in and the beach is only...
Distance to beach: 0.5 miles to Siesta Key
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Luxury Waterfront Condo for a Perfect Couples Getaway Private Boat Dock and Slip for Boat or Jet SkisEnjoy the ultimate coastal escape in this stunning waterfront condo, ideally located within walking distance to the beach, charming town center, boutique shopping, top rated restaurants, live music,...
Distance to beach: 5 miles to Siesta Key Beach
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About this property
Welcome to your luxury Sarasota escape, a stunning newly built two-story home designed for comfort, style, and unforgettable stays. Perfect for families, multiple couples, or group getaways, this spacious 4-bedroom, 3-bath residence comfortably sleeps up to 12 guests and offers a refined blend of modern...
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Our 3 bedroom, 3 1/2 bath beach house is located on Siesta Key and is on the gulf side of Beach Road. Our home is a standalone unit on 3 levels with 2 decks, a ground level patio, with a on e car garage. We are directly on Crescent Beach with gulf views and have a private access to the beach. It is...
Featured review
This house was great for our family. It was right on the beach and walking distance to town. It was clean and I don’t think we saw a bug inside the whole time. Great communication with the owner as well....
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Wood-Burning Fire Pit | Cable TVs With at-home conveniences and sought-after amenities at your fingertips, this well-appointed home is perfect for families looking to explore Sarasota! Bedroom: Queen Bed | Living Room: Queen Sleeper Sofa | Screened-In Porch: Queen Sleeper Sofa RESORT AMENITIES: Hot tub,...
Distance to beach: 0.5 miles to Siesta Key
Key Amenities
About this property
Recently Redecorated Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully decorated waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...
Featured review
This is such a comfortable, well decorated and fully equipped condo. The location was very quiet with nice views and in a great location for accessing the beach and siesta key. You can easily bike to siesta...
Distance to beach: 4 miles to Siesta Key Beach
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About this property
Welcome to Your Stylish Siesta Key Retreat! Discover your oasis of comfort and style in the heart of Siesta Key—just minutes from the world-renowned Siesta Key Beach and the vibrant culture of Sarasota. This thoughtfully designed 2-bedroom condo perfectly blends modern elegance with laid-back coastal...
Featured review
My husband and I stayed here with our dog.. overall we where pleased . Clean and comfortable nicely decorated but could use a new mattress in the master....also the shower curtain rod is rusted and needs...
Distance to beach: 7 miles to Siesta Key Beach
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About this property
Luxury lakefront home on a quiet cul de sac located in pristine Palmer Ranch. Kick back on the covered front porch and relax in the glider and rocking chairs. Soak up some sun in the screened in lanai with heated saltwater pool overlooking the lake. Enjoy community amenities such as the clubhouse, lighted...
Distance to beach: 5 miles to Siesta Key Beach
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About this property
Property Description Welcome to your Sarasota escape—just 8 minutes from world-famous Siesta Key Beach! This beautifully updated 3-bedroom, 2-bathroom home sleeps up to 10 guests, offering the ideal blend of comfort, style, and convenience for families and groups alike.Inside, you’ll...
Distance to beach: 2 miles to Lido
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Relax at this lovely comfortable and spacious one bedroom or studio apartments with gorgeous new inground swimming pool at the Southside Village Resort. Check out our website for all the various options that are available. We are located in the wonderful Southside Village, also known as the Hillview...
Featured review
Fantastic. Like home away from home. great Hosts and beautifully located. Flat was sparkling clean and jason and Dee and their son Storm always on hand for any help required. We can only highly reccomend...
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Escape to Bee Lovely Farms — a certified organic, regenerative paradise nestled among majestic ancient oaks, a gentle creek, and a peaceful natural spring. This chemical-free haven (no synthetics, GMOs, or additives) offers the ultimate tranquil retreat to reconnect with nature, slow down, and experience...
Distance to beach: 2 miles to Siesta Key Beach
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About this property
Newly renovated water view home - Walk to the beach, boat rentals, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic home, grab your beach gear and take a short walk or bicycle ride and you'll hit the beach. This rental is close to everything....
Featured review
Great place to stay not crowded once the construction is done this will be best plac3 on the island to stay
Distance to beach: 11 miles to Siesta Key Beach
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About this property
Step into your relaxing getaway in beautiful Sarasota, Florida! This thoughtfully designed townhome offers the perfect blend of modern comfort, convenience, and charm—just a 20-minute drive to Siesta Key Beach, ranked the #1 beach in the U.S.With sleek fixtures, updated appliances, and warm...
Featured review
We had a very relaxing stay at this brand new, super clean, comfortable townhouse. Our host was so understanding to help accommodate my husband and I at the last minute! Since this was a new rental, there...
Key Amenities
About this property
Located in a quiet cul-de-sac, this property offers a peaceful and tranquil setting. Away from the hustle and bustle of the city, you can enjoy a serene and calm environment in your own home.The private lanai with a saltwater pool provides a secluded outdoor space where you can relax and unwind. Whether...
Featured review
Impressed with this rental as the home was tastefully updated and in excellent condition. Host responded to our issue with shortage of hot water in one of the showers and a p-lumber arrived promptly to...
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Imagine enjoying a glass of fine wine on a private balcony, marveling at the spectacular views of a championship golf course! Well, this stylish 3BR, 2BA gem overlooks the 5th hole of the Wellen Park Golf & Country Club, offering unparalleled comforts and conveniences in a prime, well-connected location....
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Siesta Key Family Getaway – Renovated Pool Home w/ Mini Putt & Outdoor Games! Bring the whole family to this beautifully renovated Sarasota pool home, located just 15 minutes from the world-famous Siesta Key Beach! This bright and stylish 3-bedroom, 2-bath retreat comfortably sleeps up to 10...
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Apr-Dec: $1200/week, $2990/month Dec-Apr: $3500/week, $12,990/monthPOOL AREA & LAKE-VIEW, KING BED, WOOD-FLOOR and FREE WIRELESS HIGH-SPEED INTERNET all for the LOWEST PRICE in the area !!! - 5 mins from the whitest sands of Siesta Beach!!! WORLD-CLASS RESORT! Or Sister villas with tropical garden...
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A Great Home Away from Home Boatyard Gated Community Comfy Lanai for relaxing and entertaining Bamboo Wood Floors 2 bedrooms (one king and one queen bed) and 2 bathrooms Heated Pool Upgraded features include new paint and wonderful main bedroom walk in shower Wonderful fishing with several...
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Turnkey furnished home, 3 bedrooms, 2 bathrooms, 2 car garage, king bed in master bedroom with walk-in shower, soaking tub and large walk-in closet. Queen beds in the 2 guest rooms. Heated private pool.
Distance to beach: 0.5 miles to Siesta Key Crescent Beach
Key Amenities
About this property
Recently Remodeled Luxury Waterfront Condo – Perfect Couples’ GetawayEnjoy the ultimate Siesta Key escape in this beautifully remodeled waterfront condo, complete with a private boat dock and slip for boats or jet skis. Ideally located, you can walk to the beach, village shops, top-rated...
Featured review
Beautifully decorated condo in prime location. Extra clean and upscale. Best location on the harbor with water views and walking distance across the bridge onto Siesta Key's Tiki Bar. Owner is a pleasure...
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This newly remodeled two-bedroom home offers the perfect Sarasota getaway. Located just minutes from world-famous Siesta Beach, the property features a brand-new kitchen with modern appliances, 2 fully renovated bathroom, and stylish upgrades throughout. Bright, clean, and thoughtfully designed, this...
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Contact: Erana Pulli or Joesgirl16@ Newly renovated condo. First-floor end unit with a beautiful, private courtyard. Large, light, bright, and airy best describes our home! Granite countertops and stainless steel appliances are found in our eat-in kitchen. Another large dining table off the living area....
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2br/2ba first floor condo, Situated a short 5-minute drive from the cool emerald waters of Siesta Key Beach, on the North edge of Palmer Ranch. This tropical resort community is a relaxing oasis under the warm skies of the Gulf Coast. With its swaying palms, shimmering lake views and world-class resort...
Featured review
Excellent location close to everything. Clean, private patio. Eva was an excellent host, quick to respond to any questions. I would stay here again
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About this property
Beautiful townhome condominium. Large courtyard with private pool. Small association, only 12 units. Very private. Off Sarasea Circle. 2 minute walk to beach, restaurants and stores. Private off-street parking for 2 cars. 2 outside decks overlooking courtyard.
Distance to beach: 14 miles to Siesta Key Beach
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About this property
Our penthouse condo is located in Sarasota (Manatee County), Florida within the Palm Aire residential condominium community at Palm Aire at DeSoto Lakes, Inc., Golf Side. It is uniquely situated on the top floor of the only 4-story building erected within the Golf Side community. Directly across from...
Featured review
Condo was very comfortable for 2 people. If you don’t mind a queen size bed. Great view of golf course off back glassed in sitting area. Though this unit doesn't come with golf privileges. It is very...
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Situated on the Sarasota Intercoastal Waterway just South of the Stickney Point Bridge on the mainland, our 2 bedroom, 2 bathroom with Bonus room awaits you! Park your boat right outside your door with the 36 ft. boat slip that comes with this property! Conveniently located within walking distance...
Featured review
The location is amazing, the condo is beautiful and the owner is awesome. The beach is a short 10 min walk, as well as numerous restaurants/bars and coastal shops. There are a couple of different free...
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About this property
Newly renovated, professionally decorated, beautiful 2bd/2ba is fully furnished, all you need is your clothes, flip flops and toothbrush. Fully stocked with all necessary items to enjoy your stay. Heated pool, quiet neighborhood, small complex, friendly neighbors.
Key Amenities
About this property
This newly decorated luxury condominium is located in The Boatyard, a highly sought after, gated community on the intracoastal. It is within walking distance to gorgeous Siesta Key Crescent Beach, many water sport activities, shopping, restaurants and more. Private boat slips are also available, right...
Distance to beach: 2 miles to Siesta Key beach
Key Amenities
About this property
OUR RATES:June-November $1999 December $3000 January $3900 February-March $4500 April $2500 May-December $1999*Calendar months only. *Pet Friendly, Private Yard, First Floor Unit. *Community pool and gym...
Featured review
We stayed here for a clinical rotation from July - October at the Oasis on Osprey. It was truly a wonderful experience. Ana was always so helpful and attentive whenever we needed something. The area surrounding...
Distance to beach: 2 miles to Siesta Key Beach / Cresant Beach
Key Amenities
About this property
Quiet, private and pet friendly 2 bedroom, 2 bath, swimming pool home in Gulf Gate just 5 minutes to Siesta Key and her Beaches! Your Rental Fee includes the following (Rent, Cleaning Fee, Florida 12% taxes, Cable, Water & Utilities). Pet Fee additional to rental fee. NO Owners or Service Fees,...
Featured review
We thoroughly enjoyed this 2 bedroom, 2 bathroom with dedicated office space and pool gem of a rental! This was our first time taking an extended vacation (1 month) over the typical week or two and so we...
Distance to beach: 9 miles to Siesta Key
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About this property
This beautifully renovated home offers an open-concept living space, ideal for those looking to enjoy comfort and style. With two spacious bedrooms and two well-appointed bathrooms, this home is perfect for relaxation and privacy. Relax and enjoy the outdoors in your private lanai area. Located just across...
Distance to beach: 1 miles to Siesta Key
Key Amenities
About this property
OUR RATES:June-November 2025 $2250 December 2025 $3000 January 2026 $4500 February 2026 $5000 March 2026 $5000 April 2026 $3000 May-December 2026 $2250*Calendar...
Featured review
It was a pleasure working with Ana (and her husband). The unit was clean, modernized, and comfortable. The area was very nice, quiet, friendly neighbors and kept clean. Location was good, plenty of restaurants...
Distance to beach: 3 miles to Lido Beach
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About this property
Your home away should feel like home. This 2 bedroom 2 bath villa is smartly decorated and equipped with all the things necessary for comfort and practical living. Fully furnished with comfort in mind. The primary bedroom has a queen-sized bed, an en-suite bath, walk-in closet and sliders to the screened...
Featured review
We loved our stay at the hidden gem! The kitchen is stocked with everything you need. Lots of towels, beach towels, and sheets. Supplies for a beach day are also provided. The location is great-very close...
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Escape to your own slice of paradise in the heart of Sarasota's coveted Gulf Gate community with this beautifully updated 2-bedroom, 2-bathroom retreat, designed with a relaxing stay in mind. Featuring a heated, caged pool, and just moments away from the world-renowned Siesta Key Beach, this gem...
Distance to beach: 50 yards to Lido Beach
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About this property
Welcome to our stunning ground floor condo, nestled directly on the pristine Gulf of America along a tranquil stretch of Lido Beach. Say goodbye to stairs and elevators – step right into your paradise!Completely renovated in 2025, this condo offers a fresh and modern retreat, designed with...
Featured review
We rented this gorgeous Condo for the month of March, 2024. First of all, the location is perfect, right on Lido Beach with a pool onsite and right down the street from St. Armand's Circle in Sarasota....
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For less than you would pay for a small 3 star hotel room, you can rent our turn-key furnished condo overlooking Bobby Jones golf course. NO hurricane damage. Up 5 steps from your enclosed stone lanai to your wood deck. Available today at off season rates. One month minimum.Tucked behind Bobby...
Featured review
We actually stayed at a different one from what was listed owner has 9 rental properties. Overall was fine. Outside could use updates.
Distance to beach: 4 miles to Siesta Key Beach
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About this property
Newly renovated 2br /1 ba, shower cubicle, 980sqft, ground floor, private backyard, condo in the Sienna Park, Sarasota Fl.
Featured review
I very much enjoyed staying here for two months. Everything in the condo worked well, the location was great for me and my cat. Easy to get downtown or to the beaches and many golf courses.The complex is...
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This beautiful, fully furnished condo has a spectacular view of the Golf Course at the Palm Aire Country Club. Sitting on the comfortable lanai is a relaxing way to have your morning coffee or to unwind after a day of activities. The living room/dining room combination is beautifully and comfortably...
Distance to beach: 2 miles to Siesta Key
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Stunning 2 bedroom 2 bathroom FIRST floor condo in Ashton Lakes. An assigned carport is steps away from the front door. No worries about climbing any stairs. This beautiful 1356 square foot jewel has a newer kitchen with hardwood cabinets and granite counter tops along with newer appliances . There’s...
Featured review
I would highly recommend staying at this condo as it had everything one would need to make their stay enjoyable. The location is wonderful and the condo is on the first floor which helped facilitate carrying...
Distance to beach: 3 miles to Siesta Key
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About this property
Newly renovated 1br/1ba, 2nd floor condo in the Sienna Park, Sarasota, Fl. A community pool and a tennis court are provided at 1+1 condo, which is set in Sarasota, 5 min drive from Siesta Key Public Beach. This apartment offers air-conditioned accommodation with a balcony. The apartment features 1 separate...
Featured review
We were in unit 146 and totally loved it. So clean and welcoming. Would definately rent again. Thank you!
Distance to beach: 4 miles to Lido Key
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About this property
Enjoy this delightful and brand new home located in Gillespie park. The layout of the house is very comfortable with a delightful front porch and a lanai for morning coffee in the private back yard. The kitchen is well stocked with dishes and cookware, with the newest appliances. It is fully furnished...
Distance to beach: 5 miles to Siesta Key Public Beach Access
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Come and unwind in this quiet and cozy 2 br/1.5 ba, first floor end unit condo, situated just a short 10 minute drive to the cool emerald waters of Siesta Key, named the nation's best beach - twice! Relax in this tastefully furnished condo located in a small, quiet community, surrounded by grocery...
Featured review
We had a wonderful stay in this beautifully decorated and updated condo. Enjoyed the pool. The place was quiet and close to the beach. The owner was very friendly and accommodating. We loved it so much...
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About this property
Fantastic totally remodeled vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St...
Distance to beach: 5 miles to Siesta Key Beach
Key Amenities
About this property
Our house has a renovated kitchen with newer appliances including washer and dryer in the laundry area. The two bathrooms are also renovated. Our "American Dream" is decorated and prepared to make it feel as homely as possible.Bedroom 1 has a King bed which means that 3 can fit. In bedroom...
Featured review
Our first time staying in Airbnb. Was very skeptical but because our friends stayed in this area, we decided to give it a try. Clean house! Large living room! Everything needed for dining is clean and...
Distance to beach: 4 miles to Lido Key
Key Amenities
About this property
This brand new comfortable apartment is full of light and fully furnished. The living area is sunny and is a great room design with an open kitchen. The bedroom is large and the bathroom is well designed with a walk in tiled shower. The location is sweet! Walkable to restaurants, and one block from...
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About this property
To view complete details callThis home is a beautiful waterfront beach bungalow located on Little Sarasota Bay on the desirable and less congested location of South Siesta Key, Sarasota FL. This sanctuary is within walking distance of the public amenities of Turtle Beach, the Tiki Hut Pub, Bayfront...
Featured review
This house and grounds were AMAZING! The decks, dock, and gliders were relaxing and quiet-we enjoyed the bird watching and saw dolphins on our last day! Turtle Beach is nice-not quite Siesta Key sand,...
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About this property
The house is a bright, open floor plan, 3 bedroom, 2 bath home near the Siesta Beaches. Within a 15 minute drive are numerous golf courses, Benderson rowing facility, many very good locally owned restaurants of diverse ethnicities, and large shopping malls. This property is nestled in a quiet community...
Featured review
The previous reviews discussed this home and location perfectly! Our family has been fortunate to share this experience for more than ten years. That says we love everything about our home away from home....
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About this property
Bring the whole family as this home features 3 bedrooms and 2 1/2 baths. This very spacious home is almost 2,600 square feet with plenty of room to relax. Huge open living area. You will love the fenced backyard featuring multiple seating areas and a pool to relax in. Portable putting green and safe ax...
Distance to beach: 1 miles to Siesta Keys
Key Amenities
About this property
Welcome to your stylish Sarasota retreat! This beautifully renovated 2-bedroom, 2-bathroom condo offers modern comfort and unbeatable convenience just minutes from the world-famous Siesta Key beaches. The primary bedroom has a king-size bed with an attached bath. The second bedroom has two queen-sized...
Featured review
We had a wonderful stay at this condo in Sarasota! It was exceptionally clean, comfortable, and perfectly located just across the north bridge to Siesta Key—making beach trips quick and easy. The condo...
Explore a diverse selection of monthly rentals tailored to meet your needs. Whether you prefer a cozy condo close to the vibrant downtown or a spacious home near the tranquil beaches, Sarasota has a variety of options to choose from. Enjoy the flexibility and comfort of a long-term rental in this beautiful coastal city.
Cost Savings: Monthly rentals often come with discounted rates compared to short-term stays, making it more economical for extended vacations or work assignments.
Flexibility and Comfort: Renting monthly allows you to settle into a routine and truly experience the local lifestyle. Enjoy the comfort of a home-like environment with all the amenities you need for a long-term stay.
Stress-Free Living: With a monthly rental, avoid the hassle of frequent check-ins and check-outs. Unpack, relax, and fully enjoy your time in Sarasota without the constant need to move.
Community Feel: Staying longer helps you become part of the community. Get to know the locals, find your favorite spots, and feel more at home in Sarasota.
Don’t miss the chance to stay in one of the most desirable locations in Florida. Browse our listings for monthly rentals in Sarasota and find the perfect place for your extended stay. With a variety of options to choose from, you’re sure to find a rental that fits your needs and makes your stay in Sarasota unforgettable.
Thinking about next year? Secure your spot now for seasonal rentals and ensure you get the best accommodations for your stay. Whether you’re planning a winter escape or a long-term summer visit, booking early guarantees you the perfect rental.
Furnished Rentals: Fully furnished rentals include a kitchen and all the amenities you need to live comfortably for a month or longer.
Flexibility You Need: Choose your exact move-in and move-out dates and easily book online without any additional commitment or paperwork.
Simple Monthly Prices: Enjoy special rates for long-term vacation rentals and a single monthly payment without additional charges.
Work-Friendly Spaces for Digital Nomads: Find long-term stays with high-speed Wi-Fi and dedicated working spaces, perfect for traveling professionals.
🥘 Kitchen
📶 Wi-Fi
🐾 Pet friendly
💻 Laptop-friendly workspace
🚗 Free parking on premises
Discover the Perfect Monthly Rental for Your Group
Planning a getaway with a medium-sized or large group in Sarasota? Our selection of monthly rentals includes spacious homes designed for groups of 8 or more people. Find the ideal accommodation complete with private pools, large kitchens, and ample space to relax and enjoy. Explore options with 7+ bedrooms and multiple bathrooms to ensure everyone has room to unwind.
Family-Friendly Monthly Rentals
Looking to plan a large family trip? Sarasota offers numerous family-friendly monthly rentals equipped with amenities like private pools, game rooms, and hot tubs. Enjoy activities such as biking, swimming, hiking, and more. Find roomy rentals that can comfortably house a large family with five or more beds and multiple bathrooms. Start your search now to find the perfect family-friendly rental in Sarasota.
Romantic Getaways for Couples
Browse our best offers for couples seeking a private getaway in Sarasota. Enjoy relaxing activities like hiking, swimming, and biking. Our romantic monthly rentals come equipped with jacuzzis, spas, and picturesque views of Sarasota's beautiful scenery. Plan your couple's retreat and find the perfect place to create unforgettable memories.
Winter Retreats in Sarasota
Escape the cold and enjoy the warmth of Sarasota during the winter months. Our monthly rentals are perfect for snowbirds looking to spend the winter in a sunny and pleasant climate. With average temperatures ranging from the mid-60s to mid-70s Fahrenheit, Sarasota offers an inviting escape from the winter chill.
Why Sarasota is Perfect for Snowbirds
Ideal Climate: Enjoy mild and comfortable weather throughout the winter, perfect for outdoor activities and relaxation.
Community Atmosphere: Join a vibrant community of fellow snowbirds and enjoy social activities, clubs, and events designed for winter visitors.
Healthcare and Amenities: Sarasota is well-equipped with top-notch healthcare facilities, senior-friendly amenities, and services to ensure a comfortable stay.
Recreational Opportunities: From golfing and fishing to leisurely walks on the beach, Sarasota offers a variety of recreational activities to keep you active and entertained.
Book Your Winter Stay Now
Secure your winter retreat in Sarasota by booking one of our monthly rentals. Enjoy the best that Sarasota has to offer and make your winter getaway a memorable experience. Explore our listings and find the perfect home away from home for your winter escape.
Sarasota boasts some of the most beautiful beaches in Florida, making it a paradise for beach lovers. When you stay in one of our monthly rentals, you'll have easy access to a variety of beach activities:
💰 Highest rates: In March
🎉 Busiest month: January
🏠 Popular home types: Condo and House rental
🔥 Hottest months: July and August
❄️ Coldest months: January and December
☔ Rainiest months: June and August
🌺 Best months for flowers: April and May
🌴 Peak tourist season: December to April
🍂 Quietest months: September and October
🌊 Best beach months: April and May
🏌️ Best golfing months: November to April
🎨 Top cultural events: Sarasota Film Festival (April), Sarasota Music Festival (June)
🍽️ Best dining months: January to March (Restaurant Weeks)
🦋 Nature activities peak: March to May (Butterfly watching and bird migrations)
🛶 Water sports season: June to September
🏖️ Best months for shelling: May and June
📅 Local festivals peak: December to April
Explore our listings today to find the perfect monthly rental in Sarasota, Florida, and make the most of your beachside getaway!
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