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Looking for a tropical getaway on Florida’s Gulf Coast? Our monthly rentals in Siesta Key offer the perfect long-term escape in one of the most beautiful beach destinations in the world. Whether you're planning a winter retreat or a summer vacation, Siesta Key’s pristine beaches, vibrant nightlife, and outdoor activities make it an ideal destination.
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WAKE UP TO FULL PANORAMIC GULF VIEWS. FALL IN LOVE WITH SIESTA KEY.This Beach Condo has Over 125 5-Star VRBO Reviews out of a total 135 reviews. Imagine waking up each morning to breathtaking panoramic views of the sparkling Gulf waters, stepping into your private enclosed lanai with a fresh cup...
Key Amenities
About this property
Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size...
Featured review
The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.
Key Amenities
About this property
Key Differentiators & Amenities•7 properties away to step onto the access of Siesta Key Beach (#1 beach in the US) •Ample parking for RV, boat, and multiple vehicles •EV charging station onsite •Private saltwater pool (fenced backyard) •Pet-friendly: beds, crates,...
Key Amenities
About this property
NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN,...
Featured review
This 4 bed 2 bath villa was perfect for our family vacation! It's spacious with towels, chairs and wagon for the beach! Ali and her team are great!
Key Amenities
About this property
Your private Siesta Beach escape! Walk or bike to sand, unwind in the heated saltwater pool or Sauna and bring your furry friends along!Key Differentiators & AmenitiesSought-after Siesta Key Family & Pet friendly location—easy access to the beach, village, shops, restaurants, coffee...
Featured review
The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience...
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Distance to beach: 100 feet to Crescent Beach
Key Amenities
About this property
Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date...
Featured review
The area: The general area of the condo was a fun place to visit. Plenty of stores within walking distance (just across the street). More than ample restaurants from which to choose. If you are heading...
Key Amenities
About this property
Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and...
Featured review
This is a beautiful condo in Bayside Club resort. A gated community. Well cared for. This condo is just 30 feet from one of the pools, tennis courts and pickle ball courts. It’s a short walk to...
Distance to beach: 0.1 miles to Siesta Key Beach
Key Amenities
About this property
Skip the parking hassle — you’re just steps from Siesta Key Beach, consistently ranked #1 in the U.S.This newly upgraded 2-bedroom, 2-bath condo is perfectly located directly across from the beach and minutes from Siesta Key Village. Walk, bike, or hop on the free trolley to reach top...
Featured review
Responsive, informative credible host. Exact match to published stay info. Accommodations were exceptionally clean and comfortable. I felt as if I were home. The home has everything that you could ask for...
Distance to beach: 0.3 miles to Crescent Beach
Key Amenities
About this property
Discover the ultimate Siesta Key getaway with this beautifully appointed, smoke free, 3-bedroom Townhouse, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation...
Featured review
The condo was great for our stay in Crescent beach for the month. It has everything you need to enjoy your stay at the beach. From beach chairs,bikes,umbrella's, towels and so much more. The pool was very...
Key Amenities
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The Condo Bay side water views; 2nd floorPrimary: King BedPrimary bath: tub/shower comboGuest: 2 twins/convert to KingGuest bath: tub/shower comboLiving Room: Sleeper Sofa
Key Amenities
About this property
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 from inside and outside and have a private access...
Featured review
Fantastic house & great location! The owners have thoughtfully stocked the house with all the beach necessities. We enjoyed exploring all the nearby shops & restaurants & appreciated the bikes that were...
Distance to beach: 0.1 miles to Crescent Beach on Siesta Key
Key Amenities
About this property
This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling...
Featured review
The booking and check in process was easy. In addition , we appreciated how fully stocked and clean the condo was. Getting around the island was simple (walking and riding the tram). Best of all, the beach...
Distance to beach: 0.2 miles to Siesta Key
Key Amenities
About this property
NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach...
Featured review
This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short...
Key Amenities
About this property
Waterfront Pool Home – Walk to Siesta Key Village & BeachPrime Siesta Key LocationWelcome to your private island getaway in the heart of Siesta Key.Located on a quiet waterfront street just steps from Siesta Key Village and a short walk to the world-famous white sand beaches, this...
Featured review
This home is in one of the best locations on Siesta Key. It’s a little bit older style of a beach house beds were comfortable outside furniture and inside furniture could use some updating. I think they’re...
Distance to beach: 0.6 miles to Siesta Key Beach
Key Amenities
About this property
Welcome to your slice of paradise on Siesta Key—where coastal charm meets everyday convenience. This beautifully maintained single-family pool home offers the perfect blend of privacy, comfort, and proximity to the island’s natural beauty. Step outside and enjoy the lush, landscaped backyard,...
Key Amenities
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This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing...
Featured review
This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting...
Key Amenities
About this property
Summer Cove on Siesta Key is life at its finest. This gated community on Little Sarasota Bay offers a spacious 2 bedroom, 2 1/2 bath unit of luxury with the sophistication and conveniences of the finest resort located on the Key within minutes to the #1 beach in the US - Siesta Key Beach. The unit is...
Distance to beach: 0.0 miles to Siesta Key Main Beach
Key Amenities
About this property
Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. Walk to beach. King bed in bedroom (and a Queen bed in living room if needed). Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness...
Featured review
what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina,...
Distance to beach: 1 miles to Crescent Beach
Key Amenities
About this property
E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen provides state-of-the art appliances. There is washer and dryer conveniently by the kitchen. Ammenities...
Featured review
The HOST of this unit (E91) was the most prepared HOST of all time. She had every box checked inside the condo to make our stay effortless. The grand-children loved the bunk beds in the second bedroom...
Distance to beach: 0.3 miles to Siesta Beach
Key Amenities
About this property
This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! There is a wonderful outdoor living space with dining table and lounging area, living room, dining area, kitchen, office as well as laundry room. All of the bedrooms have an ensuite...
Featured review
Thanks to Stephanie for excellent communication and special thanks to MJ who was very helpful and quickly available during our stay. This condo is beautiful and has an excellent location. It's a 3 minute...
Key Amenities
About this property
MONTHLY RENTAL. Introducing our BEAUTIFUL NEWLY RENOVATED LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or...
Featured review
Chris and Jeannie could not have been more accomodating hosts . The unit was beautiful and well appointed. Residents of the Casarina were extremely friendly. Looking very much forward to returning next...
Distance to beach: 400 feet to Siesta Beach
Key Amenities
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Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway....
Featured review
This house was perfect for our group. With five bedrooms and four bathrooms, everyone had plenty of space and privacy, and the layout made it easy for a larger group to spread out without feeling crowded.The...
Key Amenities
About this property
Beautiful 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With a king...
Featured review
Half a mile walk to Siesta Key Village. We had a wonderfully updated condo. Maria and her husband were great landlords. We had a beautiful view every morning of the sunrise and every night on the private...
Distance to beach: 250 feet to Siesta Key
Key Amenities
About this property
On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis...
Featured review
This was our third stay in this apartment, and everything was perfect as always! Great location, fully equipped with everything you need, and the rental process was easy and hassle-free. Thank you! We would...
Distance to beach: 400 feet to Siesta Beach
Key Amenities
About this property
Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor...
Featured review
This home is absolutely beautiful and spotless! Has every amenity you could want and is so close to the beach! Working with the host was very easy and very accommodating. You would totally enjoy this stay,...
Distance to beach: 0.5 miles to Siesta Key Main Beach
Key Amenities
About this property
Sweet Siesta Key Condo walking distance to #1 Beach in America! Spacious and Quiet One Bedroom with King Bed, Screened Lanai, Wireless Internet, 2 Flat screen TV’s, covered parking space, full kitchen with amazing water filtration system. Easy Walk right over to Siesta Key Main Beach, and their...
Featured review
Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my...
Distance to beach: 0.4 miles to Siesta Key Beach
Key Amenities
About this property
Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away from...
Featured review
The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar...
Distance to beach: 800 feet to Siesta Key Beach
Key Amenities
About this property
Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master...
Distance to beach: 0.7 miles to Siesta Key Beach
Key Amenities
About this property
**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...
Featured review
5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...
Key Amenities
About this property
Wake up to breathtaking views of the award-winning Siesta Key Beach from every room in this stunning, updated two-bedroom, two-bath condo. Designed for relaxation, this bright and airy retreat features an open floor plan, neutral tile, and an abundance of natural light. Step onto the screened-in lanai...
Key Amenities
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Escape to paradise in this stunning 2-bedroom apartment directly across from the pristine white sands of Siesta Key Beach! This modern coastal retreat features a king bed and two full beds, perfect for families or groups. Enjoy the convenience of included Wi-Fi and the tranquility of a non-smoking environment....
Distance to beach: 0.5 miles to Siesta Beach access 7
Key Amenities
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The Canal Place Bungalow Old Florida Charm on the Water in Siesta KeyEscape to the timeless beauty of Siesta Key with a stay at Canal Place, a spacious 2-bedroom, 2-bath bungalow full of vintage Florida character. Nestled along a peaceful canal with its own dock, this retreat blends classic charm...
Featured review
I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta...
Key Amenities
About this property
Discover the perfect balance of comfort, charm, and Florida sunshine in this beautiful home, ideally located just a short stroll from the world-famous Siesta Key Beach and the lively Siesta Village, filled with restaurants, cafés, and boutique shops. Bedrooms & Comfort Left side of the home: • One...
Featured review
A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit...
Key Amenities
About this property
Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this remodeled home delivers on design, location and lifestyle. Featuring four bedrooms, two-and-one-half baths and washer & dryer. Please note that the garage and boat dock is not available but there is plenty of parking in the...
Key Amenities
About this property
Escape to paradise in this stunning two bedroom apartment located just steps away from the pristine white sands of Siesta Key Beach. This modern coastal retreat is designed for comfort and convenience, featuring a spacious layout with a king bed, a queen bed, and a full bed, making it the perfect choice...
Key Amenities
About this property
Escape to this charming 3-bedroom house on Siesta Key, offering a private pool and a 2-car garage just a short distance from the beach. Enjoy amenities like a fully-equipped kitchen and a charcoal grill, which is perfect for family gatherings. With multiple TVs and high-speed internet, relaxation is guaranteed....
Key Amenities
About this property
Indulge in a luxurious stay at this completely renovated home in the center of the island, offering a private pool and a tranquil atmosphere. , you can immerse yourself in the beauty of this home. This home is ideal for families with children and infants, providing a perfect blend of comfort and convenience....
Key Amenities
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Available October 15, 2026 through March 15, 2027. The ideal rental is the full seasonal period, although other stays of two months or longer may be considered.Spend the winter where everything is within walking distance.Welcome to your home away from home in Villa Navarra, an intimate 16-unit...
Key Amenities
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Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry...
Distance to beach: 0.1 miles to Siesta Beach
Key Amenities
About this property
Our new unit are truly a site to see. 2 BR / 2 BATH completely remodeled, newly furnished unit with fully equipped kitchen, cable TV, WiFi, and washer/dryer. Enjoy a Resort Style pool area beautifully landscaped with 2 Tiki Bars and plenty of space to work on your tan! Not to mention a grassed area for...
Featured review
Roomy, very clean, very accommodating staff. Pool was super clean and warm. Walk to everything., don't need a rental car!
Key Amenities
About this property
Discover your Siesta Key oasis! This gorgeous 4-bedroom, 3-bath house boasts a private pool, updated interiors, and a prime location near the beach. Enjoy a fully-equipped kitchen, high-speed internet, and a spacious layout that comfortably sleeps 10. Relax on the covered lanai, soak up the Florida sun,...
Distance to beach: 0.5 miles to Siesta Key Main Beach
Key Amenities
About this property
Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo,...
Featured review
Thank you again, Barbara and Angelo, for providing your vacation home for our annual trip to Siesta Key. November is our favorite month there, with perfect temperatures and a tranquil setting. The property...
Distance to beach: 0.3 miles to Siesta Key Beach
Key Amenities
About this property
Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable...
Featured review
We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this...
Key Amenities
About this property
Welcome to paradise! Your tropical oasis awaits you in this spacious two-story home. This stunning 4 bedroom, 4.5 bath luxury home with a private heated pool is just blocks from Siesta key beach! Five star amenities include; expansive gourmet kitchen with granite counter tops, handsome wood cabinetry,...
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
Key Amenities
About this property
*Calendar month rentals only*July-November (monthly lease) - $3500 per month plus utilities and tax. December - $7900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 days prior for monthly rentals. Check the...
Featured review
I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors...
Key Amenities
About this property
White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.MESSAGE ME FOR LINK TO THE BOOKING WEBSITE AND...
Featured review
Had a great time at White Sands #308. Close to the beach and a very nice pool with grills! Super easy to get around with the trolly and “frog hop” so you don’t have to drive. Highly recommend.
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
Key Amenities
About this property
*Calendar month rentals only*May-November (7-month lease) - $3000 per month plus utilities December - $6900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 prior for monthly rentals. Check the calendar for...
Featured review
It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring...
Key Amenities
About this property
- Check in: 15:00 - 20:00 Check out until: 10:00 Number of guests included in the base price: 4 Maximum number of guests: 4
Key Amenities
About this property
Indulge in a luxurious escape at this contemporary Siesta Key home. Featuring 4 bedrooms, 4 full bathrooms, and an elevator, this stunning property offers the perfect blend of comfort and style. Enjoy a private backyard oasis with a swim/spa, and stay connected with included Wi-Fi. This home is ideal...
Key Amenities
About this property
Your home away from home on Siesta Key with 2 bedrooms 100 steps to the beach. This fabulous condo features a comfortable king bed, a full bed, and a twin bed, perfect for families or friends traveling together. Guests enjoy two bathrooms, each equipped with a refreshing shower and a hair dryer for convenience....
Featured review
A truly perfect condo on the beach with fantastic views of Crescent Beach and Siesta Key Beach. This ocean view unit, also overlooks the largest pool of three available on this well landscaped, large gated...
Explore a range of monthly rentals in Siesta Key, from beachfront condos to luxurious homes with ocean views. Whether you want to be close to Siesta Beach or prefer a quiet retreat near Crescent Beach, there’s a rental to suit your needs. Enjoy the comfort of a long-term stay in this coastal paradise.
Don’t wait to secure your ideal long-term rental in Siesta Key. Browse our listings and find the perfect property for your extended stay. Whether you’re looking to escape the cold or enjoy a warm, sunny vacation, Siesta Key is the place to be.
Booking in advance is the best way to ensure you get the rental you want, especially during the busy winter months when Siesta Key is in high demand.
Group-Friendly Rentals
Planning a group vacation or family reunion? Siesta Key offers spacious rentals with multiple bedrooms and large living spaces, perfect for groups looking to enjoy a relaxed beach getaway.
Family-Friendly Monthly Rentals
Siesta Key is ideal for families with attractions like Siesta Beach, Point of Rocks, and Turtle Beach. Our family-friendly rentals provide ample space, outdoor areas, and proximity to kid-friendly activities like boating, snorkeling, and wildlife viewing.
Romantic Getaways for Couples
Siesta Key’s romantic sunsets and tranquil beaches make it a great destination for couples. Enjoy cozy monthly rentals with ocean views, private pools, and easy access to intimate dining and beachside strolls.
Winter Retreats for Snowbirds
Siesta Key is a favorite among snowbirds seeking to escape the cold northern winters. With its warm weather, stunning beaches, and a laid-back atmosphere, it’s no wonder snowbirds flock here each winter. Our monthly rentals provide a comfortable and convenient home base for an extended stay.
Don’t miss out on your chance to spend the winter in paradise! Reserve your long-term rental in Siesta Key today and enjoy everything this beautiful destination has to offer.
Siesta Key is known for its stunning beaches and outdoor adventures. Staying in one of our monthly rentals puts you close to:
💰 Highest rates
December through March
🎉 Busiest month
February
🏠 Popular home types
Beachfront condos and single-family homes
🔥 Hottest months
July and August
❄️ Coldest months
January and December
☔ Rainiest months
June through September
🌺 Best months for flowers
April and May
🌴 Peak tourist season
December through March
🍂 Quietest months
September and October
🌊 Best beach months
March through May
🏌️ Best golfing months
November through April
🎨 Top cultural events
Siesta Key Crystal Classic Sand Sculpting Festival (November), Siesta Fiesta Art Festival (April)
🍽️ Best dining months
January through March
🦋 Best months for nature activities
March through May
🛶 Best water sports season
June through September
🏖️ Best months for shelling
May and June
📅 Local festivals peak
November through April
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