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Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat DocksLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the...
Featured review
Great location on Turtle Beach, quieter and less busy than Siesta Key Beach. Great accommodations direct access to beach with boat slip out back to get out onto Sarasota bay. Nicely equipped condo, although...
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Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building...
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Fisherman's Cove Condominiums have the best Location on Siesta Key! It is surrounded by water with the Gulf of Mexico on the west side and a private lagoon that leads to the inter-coastal waterway (ICW) on the east side. Swim, surf, boat, kayak, paddle board, fish, gather seashells and shark’s...
Featured review
First floor walk out directly on the beach. I had seen photos of the brand new overhaul, however I was not prepared to be over whelmed by the beauty when we walked in. It literally took my breath away!...
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Newly fully luxuriously decorated beach Townhouse is just a few steps from the private white sandy US #1 rated Siesta Key Beach. This 2 bedroom 2.5 bath is everything you want and more! It will exceed your expectations. Look no further Check-in time: 15:00 Check-out time: 11:00 Last Minute Discount:...
Featured review
We have had numerous beach stays in the area, and this one met every expectation we had! It's a bit farther from the downtown area than what we were used to, but the walk was totally doable and the free...
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Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience...
Featured review
My daughter and I went down and enjoyed the place. The convenience to get to the beach was great and it was such a big area!! Loved walking around the key!! Love Siesta Key and this was a fabulous place...
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Distance to beach: 0.2 miles to Siesta Key
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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...
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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,...
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This luxury two-bedroom/two-bath condo at Sunset Royale will deliver you to a beach experience that will make if very hard to do anything other than take in the view and enjoy your condo surroundings or walk over to the beach and experience the view.This 1,800 square foot two-bedroom and two-bath...
Featured review
had a lot of great options that were not found on the typical rental sites. I sent multiple requests and received feedback from most of the requests that I submitted. The owner of the unit we ended up booking...
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VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village...
Featured review
The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.
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CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...
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This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout....
Featured review
The owners make your arrival amazing. You have to experience it to know. The view is breathtaking. Both the back of the property and the front have spectacular views. The property is perfectly equipped...
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Beautifully renovated one bedroom King size super comfy mattress. Full bathroom with shower/tub. Fully remodeled kitchen with dishwasher. Living room has queen size memory foam sleeper sofa. Comfortably sleeps 4. Free parking, wi-fi, smart TVs in bed and living room. Heated pool, tiki hut on the bay,...
Featured review
We just returned from our getaway at Varinia’s home. It was perfect in every way. Short walk to the pool, short walk to the beach and all needs were met. The beach wagon, chairs and umbrellas were excellent...
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We are a small family owned resort on Siesta Key offering daily rentals Villa 4 is newly renovated Featuring 1 King bedroom, Large shower in bathroom, Large Smart TV in the Living Room, Sofa and Table and Chairs. A/C, Kitchenette with Fridge Freezer, Pop Up Toaster. Coffee Maker, K Cup, Single...
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A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened...
Featured review
Our stay at Aloha Kai was amazing! The unit was spacious, clean and beautifully decorated. Plenty of space for our family of six, all adults. The outside space exceeding my expectations. Plenty of seating...
Distance to beach: 0.2 miles to Siesta Key Beach
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Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom...
Featured review
The place was very clean. The location was perfect for beach trips and trolleys for visiting the village.
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Welcome to your little piece of paradise on Siesta Key—an oceanfront condo where the view is the experience.This fully renovated 2-bedroom, 2-bath unit offers direct, unobstructed Gulf views from the living room, kitchen, master bedroom, and lanai. There are no angled views or buildings in the...
Featured review
Our stay in Siesta Key at this rental unit was absolutely amazing! The proximity to the ocean allowed us to see incredible wildlife, including dolphins right from our lanai. The sunsets in the evenings...
Distance to beach: 200 yards to Crescent Siesta Key Beach
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Welcome to Paradise at Midnight Cove 1 Siesta Key, FloridaLocated on consistently top-ranked Siesta Key Beach, our beautifully remodeled bayside condo at Midnight Cove 1 offers the perfect blend of luxury, comfort, and island charm for your next tropical getaway.Nestled within a lush, gated community...
Featured review
Sandy's condo is AMAZING! Clean, well furnished with very comfortable beds. Location is awesome and Sandy was very nice, and easy to work with! I rate it 6 out of 5 stars!
Distance to beach: 950 feet to Crescent Beach
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Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed...
Featured review
Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The...
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This stunning, fully remodeled 2-bedroom, 2-bathroom Siesta Key condo offers the ultimate beachfront escape. Located on the serene south end of Siesta Key in Fisherman’s Cove, the condo faces the Gulf of Mexico and is less than100 feet from the water. Enjoy beautiful tile flooring, a gourmet kitchen...
Featured review
We had an absolutely wonderful stay! The condo was perfect—beautifully remodeled, tastefully furnished, and situated right on the beach with incredible views of both the Gulf and the bay and easy access...
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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 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...
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RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large...
Featured review
This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen...
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SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the world...
Featured review
Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate
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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!
Distance to beach: 0.1 miles to Siesta Beach
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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!
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Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is...
Distance to beach: 0.1 miles to Crescent Beach on Siesta Key
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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: 250 feet to Crescent Beach
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Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 10% to 25% Discounted Rental Rates from $2,095 to $3,921 /Wk Depending on the Season and payment method ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $366 to $855 /Wk from...
Featured review
The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!
Distance to beach: 0.0 miles to Siesta Key Main Beach
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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: 0.6 miles to Siesta Key Beach
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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,...
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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...
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Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.
Featured review
Our family loved staying here and have already looked into coming back! The location can’t be beat as it is on the first floor of the tower which makes the beach just steps from your door. We enjoyed...
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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...
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Crystal Sands, Siesta Key, SarasotaReduced summer rates.Amazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the beach, or have a glass...
Featured review
We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!
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This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart...
Featured review
My family absolutely loved this home. We’ve been traveling to Florida for almost 10 years and have stayed in many different rentals. This was our second year in Siesta Key, we loved it so much we came...
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Located in beautiful Siesta Key, Fl. this bayside condo is full of amenities needed for a relaxing beach vacation. Two tennis courts with Pickleball available, two heated pools, covered private parking, outdoor gas grills, boat docks, outdoor bathrooms within this private, gated community.Walk to...
Featured review
Very family friendly, had beach toys and beach towels available, along with a beach tote. Host provided us a pack and play on request. Beautiful bay facing condo and easy walk to gulf side.
Distance to beach: 0.3 miles to Crescent Beach on Siesta Key
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Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal...
Featured review
We absolutely loved our stay in Siesta Key! The location was beautiful, with an incredible view of the bay right outside our door. Staying on the ground floor made the experience even more special… every...
Distance to beach: 400 yards to Crescent Beach
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Welcome to The Sand Dollar, a beautifully maintained beach-to-bay villa in the sought-after Horizons West community on Siesta Key. All the amenities of a resort, with the privacy and charm of a standalone beach villa.Start your morning with coffee overlooking the Intracoastal Waterway, spend the day...
Featured review
Villa E8 was attractively decorated and well equipped. Property was clean and well maintained. Property management company was very responsive. Weekly linen service was a nice surprise.
Distance to beach: 0.3 miles to Siesta Beach
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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...
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Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour...
Featured review
Very convenient to ICW and about 1/2 mile to the beach. Very comfortable condo and the owner was very responsive and proactive with the information we needed.
Distance to beach: 1 miles to Crescent Beach
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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...
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Completely remodeled private villa is steps to the famous white sand of Siesta Key Beach.Bedroom 1- King bed, en suite bathroom, TV Bedroom 2- 2 Queen beds, en suite bathroom, TVOpen-concept Living, Dining, Kitchen with counter seating. Large TV for everyone to watch movies & games. Fully...
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Welcome to your slice of paradise in Siesta Key! Our updated 2-bedroom, 1-bath villa is just two villas away from the private, powdery white sands of Crescent Beach, ranked the #1 beach in the U.S. by both Dr. Beach and TripAdvisor. Enjoy complimentary cabanas and lounge chairs while soaking up the Florida...
Featured review
Looking forward to returning in the fall. So beautiful and so much to do. Great vacation spot. Villa is the perfect size for us and the grandkids enjoy it too!! Our favorite place to vacation!
Distance to beach: 0.1 miles to Siesta Key
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Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky...
Featured review
I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps...
Distance to beach: 200 yards to Siesta Key/ Crescent Beach
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Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is unit B07 in the Casa Blanca resort located on the GULFSIDE (or Beach side) of the island.It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a...
Featured review
This was our second vacation in as many years at Casa Blanca. Both times we selected the same unit number and both times we were simply delighted with the experience. Everything exceeded our expectations....
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Enjoy comfort and convenience in this well-appointed 2-bedroom, 2-bathroom villa located in Casa Blanca, just minutes from the beach, dining, and island attractions. The primary bedroom features a king-size bed with an en-suite bathroom and shower, offering privacy and relaxation. The guest bedroom includes...
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Enjoy the perfect blend of space, comfort and convenience with this large two bedroom two bathroom villa. Designed with an inviting open floor plan that flows seamlessly from the kitchen into the living room. The villa comfortably sleeps up to four guests with a king bed in the master bedroom and tow...
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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
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Villa 512 at Siesta Sands offers a charming beachside retreat where comfort and simplicity take center stage. Light-filled and welcoming, this thoughtfully designed villa features an open layout and a breezy coastal style that makes it easy to settle in and start enjoying your stay. The kitchen and living...
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Totally remodeled ground floor unit. This unit is brand new to the rental market and is a rare find. Walk out the rear Lanai door directly to the becach. You can't get any closer to the Gulf of America on Siesta Key. The open floor plan allows Gulf views from the sunroom, master bedroom, living room,...
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Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the...
Owners list their cleaning fees, taxes, and any extra charges up front, and because you book with the owner directly, you skip the booking fee the large travel sites add. Sarasota County adds a 13% tax on stays under six months.
SHORT STAY
3 nights
all in
$286/night
| $286 × 3 nights | $858 |
| Cleaning + damage waiver | $200 |
| Tax (13%) | $138 |
| Booking fee | $0 |
| Total | $1,196 |
WEEKLY STAY
7 nights
all in
$286/night
| $286 × 7 nights | $2,002 |
| Cleaning + damage waiver | $200 |
| Tax (13%) | $286 |
| Booking fee | $0 |
| Total | $2,488 |
MONTHLY STAY
30 nights
all in
$286/night
| $286 × 30 nights | $8,580 |
| Cleaning + damage waiver | $200 |
| Tax (13%) | $1,141 |
| Booking fee | $0 |
| Total | $9,921 |
The Gulf here has two busy stretches: Snowbirds fill the cool, dry winter, and families crowd the warm summer months. For swimming weather without the peak-summer heat or the June-through-November hurricane season, aim for April and May or October, when the Gulf sits in the mid-70s to low 80s and the days stay warm and dry. September, at the height of hurricane season, is the quietest and cheapest month.
| Month | Median nightly | Difference from annual | High / low air temp | Avg. gulf temp | What’s going on |
|---|---|---|---|---|---|
| January | $310 | +9% | 71° / 51° | 64° | Peak snowbird season; Sunday farmers market in the Village (year-round) |
| February | $393 | +38% | 74° / 54° | 65° | Cortez Fishing Festival, 35 minutes north |
| March | $407 | +43% | 77° / 58° | 67° | Sarasota Jazz Festival, mainland |
| April | $333 | +17% | 81° / 62° | 73° | Run/Walk for the Turtles; Sarasota Film Festival |
| May | $259 | -9% | 86° / 68° | 78° | Sea-turtle nesting begins, lights-out rule |
| June | $285 | 0% | 89° / 73° | 82° | Summer family crowds arrive |
| July | $285 | 0% | 91° / 74° | 85° | Fourth of July fireworks on Siesta Beach |
| August | $250 | -12% | 91° / 75° | 87° | Red tide possible along the coast |
| September | $233 | -18% | 89° / 73° | 85° | Peak hurricane season, lowest rates |
| October | $232 | -19% | 85° / 67° | 82° | Sea-turtle nesting season ends |
| November | $241 | -15% | 79° / 60° | 75° | Crystal Classic sand-sculpting on Siesta Beach |
| December | $275 | -4% | 74° / 54° | 69° | Christmas Boat Parade of Lights |
Based on the median Siesta Key nightly rate on FloridaRentals.com.
Siesta Key runs about eight miles, and its three beaches each anchor a different part of the island. Public beach accesses are numbered 1 through 13, but for a beach with a lifeguard, head to the main Siesta Public Beach.
Sarasota-Bradenton International (SRQ) is the close commercial gateway, about 20 minutes from the island. Tampa International (TPA) is about an hour and 15 minutes north with far more flights, worth it only if it fits your route better.
It runs on-island between Siesta Key Village and Turtle Beach, daily from about 8 a.m. to 10 p.m., and everyone rides free. For off-strip stays and quick trips to Turtle Beach, a car helps. Siesta Beach's main lot is free but fills fast.
Sarasota County's ordinance bars dogs from the sand, with an exception for service dogs. The nearest off-leash dog beach is Brohard Paw Park in Venice, about 35 minutes south.
Sarasota County bars rentals under 30 days except on Residential Multi-Family barrier-island parcels, which is why island condos can host short stays while many single-family homes carry a 30-day minimum.
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