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If you are looking for elegance, A108 is for you. If you are a sophisticated traveler and can appreciate how lovely this condominium is (as the owner spared no expense in remodeling this Gulf-front first floor vacation rental) then make your reservation now! You will walk out the lanai door directly onto...
Featured review
I wish there were more stars we could give! There aren’t enough adjectives in the dictionary to describe 108A. Immaculate beauty. Dina, Russ, and Rhonda, THANK YOU for your hospitality!
Distance to beach: 850 feet to Crescent Beach
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Direct-with-Owner Rental Discounts: Midnight Cove #532 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
This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and...
Distance to beach: 5 feet to Crescent Beach
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FULL GULF FRONT- Cathy's Crescent Condo-Beautiful turnkey 2nd floor condominium located on the pristine beaches of Siesta Key, FL. Voted the finest sand in the world. It doesn't get any better than this! This condominium is Full Gulf Front. You can view the water/beach while lying in bed from...
Featured review
Absolutely beautiful view from every room. Wonderful sunsets every night and a few steps from the beach. Kathy is a great hostess and was very responsive to all of our questions. We are already planning...
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!
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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, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...
Featured review
The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not...
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Complete remodel 2026! The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts...
Featured review
The condo was pristine and spotless! The furniture and appliances were all brand new and very comfortable especially the reclining sofa and the mattresses and pillows were also very nice. The washer and...
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This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta...
Featured review
Carrie was very informative the condo was so nice and cozy. Loved that it is right on the beach and close to restaurants and attractions. Already booked for 2027 before I left from vacation this year. I...
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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...
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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 a wonderful stay at this beautiful condo on Siesta Key! The view! Oh my goodness the view fed my soul! The location was perfect with the beach mere steps away! The condo was clean, comfortable, and...
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This two bedroom(master King bed), second bedroom double bed/ Queen bed , full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry areas. Newly remodeled,...
Featured review
The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed...
Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfron
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Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. B203 is on the second floor and the views are stunning! Our community...
Featured review
The unit we rented was clean, well stocked, and conveniently located. Upon arrival we had a minor issue. We were contacted immediately and the situation was resolved. The unit is close to multiple restaurants...
Distance to beach: 150 yards to Crescent Beach
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Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New hurricane windows and door installed in 2024. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great...
Featured review
Due to Helena, our condo was cancelled. Would have loved to be there but understand why we couldn't. Best to the owners as they recover. I am giving 5 stars because this was not the fault of the owner.
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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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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...
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Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated 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 is one of the closest condos...
Featured review
These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.
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My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)!...
Featured review
Carrie is amazing to work with, she has a beautiful rental and in an excellent location. You have the beach, paddle boarding and kayaking behind, this place is a bit of heaven on earth. We love it and keep...
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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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Experience the delightful simplicity of a tranquil beach getaway at Paisley's Casita. Nestled just a 7-property walk away from the serene vibes of Siesta Key Beach, this enchanting 150 square foot Studio Casita exudes similar charm to a hotel room whilst offering all the essential amenities for an...
Featured review
We rented this property for 5 nights for 2 people. The property was private via surrounded by a fence,provided bikes for transportation, and had an inviting back yard area with 2 chairs and grill. We were...
Distance to beach: 0.1 miles to Crescent Beach
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This amazing condo offers a Gourmet Kitchen and island. Granite counter tops, high ceilings and stainless steel appliances (including super quiet Bosch dishwasher and French door refrigerator with two ice-makers).Removed and replaced all forty year old Duct-work with brand new Flex Duct-work for improved...
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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...
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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...
Distance to beach: 20 yards to Crescent Beach, Siesta Key
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Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean...
Featured review
Nice to deal with the rent of the property , I will book again .Very easy and simple self explanation
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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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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
We had a great stay despite the weather. Amazing view!! The owners were great at communicating and really responsive. We’d love to return in the future.
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Welcome to our 3 Bedroom 2 Bathroom Siesta Key Beach House. Full kitchen. Walk to beach. We provide chairs & towels for the Beach Walk to Beach access #12 on Siesta key Lots of places to eat and drink, close by.Free WIFI Daily, Weekly rentals. Swimming Pool on site King Bed in Master...
Distance to beach: 100 feet to Crescent Beach
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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...
Distance to beach: -100.0 feet to Crescent Beach -- we are located on the beach
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Sea Crest on Siesta Key is a small 40-unit condominium complex at 1129 Seaside Drive consisting primarily of one-bedroom units with separate bedroom, one efficiency, and one two-bedroom, two-bathroom unit. A true old style Floridan resort. Enjoy our one bedroom condo just a few steps to our private...
Featured review
I was supposed be there Oct 1 to 29th, but hurricane Ian had other plans for me, Jeffrey the manager was very acommodating in making all the necessary changes to make my stay wonderfull. I ended going the...
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Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. A306 is on the third floor and the views are stunning! Our community...
Featured review
Wow!!! Where do I start? I knew we had booked the right condo when we rounded the corner and could see the Gulf. This was a present for my daughter's senior trip / 18th birthday and it did not disappoint....
Distance to beach: 100 feet to On-site Turtle Beach
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Experience true Gulf-front living at Fisherman’s Cove B103, a beautifully renovated beachfront condo located at 9000 Blind Pass Rd, Siesta Key, Florida.The virtual tour was taken in 2021. In 2024 we experienced the hurricanes which changed the beach beyond the rocks that you see in our current...
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This 5th floor two bedroom, two bath condo is just a few steps for the private area of Siesta Key Beach!. Beach chairs and beach loungers are provided at the beach entrance. Shade in one of our Beach cabanas. Private parking under carport. Shower at the beach entrance. Wake up to amazing views on your...
Featured review
We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to...
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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 charming Siesta Key one bedroom ground floor condo is located in the highly coveted Golden Triangle...
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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Siesta Key - Ground Floor Gulf-Front Retreat - 2 BR – Free Boat Docks Located 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 is one of the closest...
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Gulf views from both bedrooms and your private screened terrace — a half-mile stroll to world-famous Siesta Key Beach.Ocean Views over palm trees visible from both bedrooms and your private screened in terrace! Walk to world famous Siesta Key Beach! 2 bedroom 2 bath is in perfect condition,...
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THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen...
Featured review
My family and I had the most amazing stay in Don & Elaine’s condo! We have been coming to Siesta Key for 6 years and this was our favorite room- best location and best view ever! We look forward to returning....
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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...
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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,...
Distance to beach: 90 feet to In front of condo!
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The new owners have spared no expense in transforming this bright, inviting waterfront condo into a luxurious coastal retreat. Completely remodeled from top to bottom, the condo features new luxury flooring, solid-core six-panel doors, fresh paint, new light fixtures, ceiling fans, and beautifully rebuilt...
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Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located 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...
Featured review
The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.
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...
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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...
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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...
Distance to beach: 100 feet to On-site Turtle Beach
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Welcome to Beachfront Serenity at Fisherman’s Cove B204, a beautifully updated Gulf-front condo located at 9000 Blind Pass Road, Siesta Key, Florida. This rare coastal retreat offers one of the most unique locations on the island—Gulf views in the front and Sarasota Bay waters just steps from...
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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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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...
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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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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...
Distance to beach: 0.3 miles to Turtle Beach
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Two-bedroom condo on the second floor overlooking the Blind Pass Lagoon. Facing the Gulf, where the sun sets in its glory with a unique and spectacular sunset every evening.Enjoy your morning coffee overlooking the Lagoon, and enjoy the sunset over the Gulf with your favorite beverage.
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You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your...
Featured review
crescent royal condos was top notch condo 409 was as clean as a surgical room the view was better than I expected beach beyond perfect location perfect if your looking for a great place this is it
Distance to beach: 20 yards to Crescent Beach, Siesta Key
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Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean...
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About this property
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated 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...
Featured review
Clean update lite filled condo close to everything All appliances work baths were clean and beds comfortable Would definitely return.
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
$413/night
| $297 × 3 nights | $891 |
| Cleaning + damage waiver | $205 |
| Tax (13%) | $142 |
| Booking fee | $0 |
| Total | $1,238 |
WEEKLY STAY
7 nights
all in
$359/night
| $288 × 7 nights | $2,016 |
| Cleaning + damage waiver | $205 |
| Tax (13%) | $289 |
| Booking fee | $0 |
| Total | $2,510 |
MONTHLY STAY
30 nights
all in
$294/night
| $253 × 30 nights | $7,590 |
| Cleaning + damage waiver | $205 |
| Tax (13%) | $1,013 |
| Booking fee | $0 |
| Total | $8,808 |
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 | $300 | +5% | 73° / 52° | 64° | Peak snowbird season; Sunday farmers market in the Village (year-round) |
| February | $393 | +38% | 75° / 55° | 66° | Cortez Fishing Festival, 35 minutes north |
| March | $401 | +41% | 78° / 58° | 71° | Sarasota Jazz Festival, mainland |
| April | $330 | +16% | 83° / 63° | 76° | Run/Walk for the Turtles; Sarasota Film Festival |
| May | $261 | -8% | 88° / 68° | 82° | Sea-turtle nesting begins, lights-out rule |
| June | $285 | 0% | 90° / 74° | 86° | Summer family crowds arrive |
| July | $285 | 0% | 91° / 75° | 89° | Fourth of July fireworks on Siesta Beach |
| August | $250 | -12% | 92° / 75° | 89° | Red tide possible along the coast |
| September | $233 | -18% | 90° / 74° | 86° | Peak hurricane season, lowest rates |
| October | $233 | -18% | 86° / 68° | 81° | Sea-turtle nesting season ends |
| November | $240 | -16% | 80° / 60° | 74° | Crystal Classic sand-sculpting on Siesta Beach |
| December | $275 | -4% | 75° / 55° | 68° | 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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