Home Vacation Condo Rentals By Owner In Siesta Key, FL

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$250.87

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ALL NEW - Resort Amenities and Beach Access

Siesta Key, Florida, United States

Welcome to Bayside Pointe - 1311, a beautifully appointed two-bedroom, two-bathroom vacation retreat nestled within the prestigious Gulf & Bay Club Bayside community on world-famous Siesta Key. Perfectly positioned just steps from the legendary white-quartz sands of Siesta Key Beach, this serene lakeside condo offers the ideal blend of resort-style living and the comforts of home.brbrStep inside and you'll immediately feel at ease in the bright, open-concept living space featuring a comfortable sectional sofa, wall-mounted flat-screen TV, and direct access to a private screened lanai. The lanai is the crown jewel of this unit — a peaceful outdoor oasis with a dining table and chairs perfectly positioned to take in tranquil lake views and lush tropical greenery, the ideal spot for morning coffee or an evening glass of wine.brbrThe fully equipped kitchen is designed for those who love to cook and entertain, featuring stainless steel appliances, a full-size refrigerator, breakfast bar seating, and abundant counter and cabinet space. Adjacent to the kitchen, an elegant dining area with a round table and chandelier creates an inviting setting for shared meals.brbrThe spacious primary bedroom is your private sanctuary, offering a plush king-size bed, ceiling fan, wall-mounted TV, and a comfortable sitting area. The en-suite primary bathroom features dual vanity sinks and a walk-in glass shower. The second bedroom is perfectly suited for families or additional guests, with a bunk bed and twin bed configuration — sleeping up to three — and its own full bathroom with a tub and shower combination.brbrGulf & Bay Club Bayside is a gated, lushly landscaped community that delivers a true resort experience. Guests enjoy access to a stunning resort-style pool surrounded by swaying palm trees and lounge chairs, lighted tennis and pickleball courts, a scenic waterfront boardwalk along the bay, and tranquil pond and lake views throughout the grounds. Each home in the community features a private garage and an in-unit washer and dryer for ultimate convenience.brbrIdeally situated at 1311 Siesta Bayside Drive on Siesta Key, you are just moments from Siesta Key Village — home to waterfront dining, boutique shopping, live music, and local charm. Siesta Key Beach, consistently ranked among the finest beaches in the United States for its powdery white quartz sand and crystal-clear Gulf waters, is just a short walk away.brbrWhether you're a family seeking a fun-filled coastal escape, a couple in search of a romantic lakeside retreat, or friends ready to soak in the Siesta Key lifestyle, Bayside Pointe - 1311 offers everything you need for an unforgettable Florida vacation.
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Bath 2

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Sleep 5

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$406.88

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ANC608 Summary:
The A

Siesta Key, Florida, United States

Summary:brThe Anchorage Resort on Siesta Key - includes resort amenity access Our 2 bedroom 2 bathroom private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer Anchorage Resort Condo 2 bedrooms 2 bathrooms Sixth Floor Condo with balcony overlooks Southern Siesta Key Fully equipped Kitchen with seating for 4 at the dining table Beach Supplies include- Chairs Beach Cart Umbrella Cooler Beach Towels Community Saltwater Pool- Largest pool on the Key Gated Community Siesta Key Trolley- free pickup in front of the resort entrance Private Beach access to Crescent Beach across the streetBEDROOMS Sixth Floor Condo Bedroom 1 One King Bedroom Ensuite Bathroom Balcony Access 47 Smart TVBedroom 2 Two Queen Bedroom Balcony Access 47 Smart TVThe Anchorage Resort Amenity Access Included with Rental Olympic-Size Saltwater pool 3 Lighted Tennis Courts- Can turn into Pickleball courts Out of Order Shuffleboard Community BBQ area Individual Picnic areas along the Canal Intracoastal Waterway Exercise Room His and Hers Saunas Bike Racks subject to availability Boat Dock Seawall- Kayak Launch Closed Coin-Operated Washer Dryer on Each FloorPool Information - Community Pool- Saltwater- Heated in winter monthsResort Parking Rules The resort allows a maximum of 2 cars Vehicles must be registered with the front office during office hoursHOA Rules Lead guest must be age 25 or older ID is checked upon registration at the resort No petsJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday only Distances from Resort to Shopping Attractions Daiquiri Deck South Siesta Key- 5-minute walk across the street Crescent Beach Private Beach Access- 7-minute walk across the street Toasted Mango Cafe - 9-minute walk Siesta Key Watersports - 6 mile Siesta Key Village- 2 7 trolley stop Publix at Sarasota Pavilion- 1 4 miles Marie Selby Botanical Gardens - 6 miles Sarasota Bradenton Airport SRQ - 11 miles Why Choose this Rental - Professionally managed to serve all your needs- Management company has over 26 years of experience hosting well over 200 000 families- Go straight to your rental with online email check-in- 24 7 on-call maintenance- Free On-Site Parking- Smoke-free and pet-free for your comfort- Towels and linens are provided- Complimentary WiFi Our Starter Welcome packet supplies - 2 rolls toilet paper per bathroom- 1 hotel-size bar soap per bathroom- 1 hotel-size shampoo conditioner per full bathroom- 1 roll paper towel- 2 packet dishwasher detergent- Size 13-gallon Trash bagsAny supplies beyond this are up to the guest to replenish we do not restock these items No salt pepper or cleaning supplies are stocked due to safety issues This is an industry-standard practice FOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS this does not apply if you are staying less than 30 nights We will collect a 1 500 deposit Balance is due 60 days prior to arrivalIf canceled 90 days or more before arrival we keep with us 250 00 1 250 00 will be refunded If canceled between 61 and 89 days prior to arrival we keep with us the 1 500 00 deposit No cancellation or modification 60 days or less prior to arrival
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Bath 2

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Sleep 4

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Exceptional(2)

$316.59

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Anchorage Resort 9th Floor 2-Bedroom Condo with Balcony- Gulf View! Pool/Beach

Siesta Key, Florida, United States

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brbrAnchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Ninth Floor Condo with balcony overlooks North-Western Siesta Key- Gulf Views!br* Fully equipped Kitchen with seating for 4 at the dining tablebr* Beach Supplies include- 4 Chairs, Umbrella, Beach Cartbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Ninth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 42 TV with cablebrBedroom 2: Two Twin Bed / Balcony Access / 42 TV with cablebrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each FloorbrbrPool Information:br- Community Poolbr- Heated brbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybr br brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.
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Bath 2

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Exceptional(52)

$275.99

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Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access

Siesta Key, Florida, United States

*** NEW *** Siesta Key beach has become known world wide for its incredible miles of soft white sand beaches and small village type atmosphere. This property is located within a community situated on these very beaches. The community offers beach access to a less crowded semi-private beach, swimming pool, shuffle board, and camp style grills. With such a central location, Siesta Key Village and South Village are just a few minutes ride away utilizing the free island shuttle or free ride services (tips only) available on the island. brbrEntering through the front door you will arrive in the living room furnished with comfortable lounge seating, TV, and dinette set. Moving towards the rear of the unit you have a 1/2 bath, great for coming in from the beach or pool and showering off. In the rear of the unit you will find the eat-in style kitchen. The kitchen is equipped with a 4 piece appliance package among other small appliances and basic to moderate cooking essentials. Access to the rear assigned parking spot is also through the back kitchen door. Back to the front of the unit, taking the stairs up to the second floor you will find two bedrooms and full bathroom. One bedroom is furnished with a queen-size bedroom set and equipped with TV. The second bedroom is furnished with two double-size beds and equipped with a TV. The two bedrooms share a full bathroom with combo tub/shower. brbrMinimum Stay Requirements: 1 week minimum reservation required mid December through mid August with 5 night minimum accepted a maximum of 30-days in advance during remaining months.
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Bath 2

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Sleep 6

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$630.75

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Luxury 2-story Penthouse Condo! Penthouse Balcony Ocean Views!

Siesta Key, Florida, United States

At A Glancebr• Community poolbr• 2-Story Penthouse Unit with Amazing Views of the Gulfbr• Walk to North Siesta Village restaurants and shopsbr• 30-night minimum stay required per HOAbrbrProperty DescriptionbrWelcome to an extraordinary vacation escape in the beautiful surroundings of Siesta Key. This exceptional two-story penthouse condo located in the waterfront community Sandy Cove offers an unforgettable vacation experience with a partial view of the breathtaking Gulf of Mexico! brbrWith three-bedrooms, three-bathrooms and two outdoor seating areas, you can soak up the sun and enjoy the tropical breezes all day long! Inside, a fully equipped kitchen awaits you, ideal for culinary adventures or easy catering. Enjoy the spacious rooms complete with walk-in closets, providing plenty of space to comfortably accommodate your personal belongings. brbrEnjoy the beautiful decor with modern, coastal furnishings, adding to the serene and luxurious feel of the property, allowing you to fully embrace the beauty and relaxing atmosphere of the coast. brbrIn addition to your private retreat, you can also take advantage of the community pool, a perfect spot to cool off or enjoy a refreshing swim. brbrExceptionally located in the heart of North Siesta Key Village, this condo affords easy access to live music, shopping, and a fantastic selection of restaurants. Whether you feel like trying local seafood, exploring boutiques or simply enjoying the vibrant local music scene, the Village has something for everyone. Come experience the perfect balance of luxury, convenience, and the captivating beauty of the Gulf Coast in this exceptional Siesta Key penthouse condo. brbrBedroom Detailsbr• Primary Bedroom: King bedbr• Additional Bedroom: Double bedbr• Additional Bedroom: Queen bed brbrAdditional Featuresbr• Essentials: This property is a vacation rental and comes fully equipped with everything you will need such as pots, pans, linens, towels including pool/beach towels, beach wagon, beach chairs, and all the beach gear you will need!br• Laundry: The condo has a washer and dryer available for your use.
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Bath 3

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Sleep 6

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$326.73

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Anchorage 607

Siesta Key, Florida, United States

We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, your eye is immediately drawn to the bright and cheery living space and wall ...of sliding glass doors that open up to the balcony. Southern exposurebathes the condo in sunshine through large sliding glass doors in each room. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: Yesbrbr- Beach Access: Privatebrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: 2 Twinsbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 6th Floorbrbr- Internet Access: Yes, Privatebrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: 88brbr- Electric Stove: Yesbrbr- View: Canalbrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Gulf View: PARTIALbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr
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Sleep 6

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Exceptional(14)

$466.64

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Anchorage Resort 3 Bedroom/3rd Floor Condo with Balcony

Siesta Key, Florida, United States

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 3 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.br* Anchorage Resort Condobr* 3 bedrooms / 2 bathroomsbr* Sleeps up to 8br* Spacious Balcony overlooking Northern Siesta Keybr* Third Floor Condo above the treetopsbr* Fully equipped Kitchen with seating for 6 at the dining tablebr* Beach Supplies include- Chairs, Umbrella, Cooler, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Second Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) 50 TVbrBedroom 2: Two Doubles Beds 19 TVbrBedroom 3: One Queen Bed 24 TVbrbrPool Information:br- Community Poolbr- HeatedbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.
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Bath 2

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Sleep 8

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Exceptional(129)

$215.8

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Steps from Siesta Village and the Beach

Siesta Key, Florida, United States

Our condo is located in the heart of Siesta Key Village which has numerous restaurants, bars, shops and a grocery store and is only 1 block from the beach! The best of both worlds as everything you need is within walking distance.brbrProperty Description - In the main room you have a queen size murphy bed with a built in couch that folds under the bed. With our small space we needed things that could function in multiple roles and will be out of the way when not in use. On either side of the murphy we have lined the wall with drawers, shelves and hanger space for your stay. Opposite the murphy bed is a modular couch and coffee table. A wall mounted 40 LED LCD TV with YouTubeTV HD service is mounted on an articulating arm and will allow you to watch while seated in the couch or while lying in bed. For temperature control we have a Daikin ductless AC/heat pump with a convenient hand-held remote control with precise temperature control. brbrIn the kitchen, there's a GE Speed cook oven which is so much more than just a microwave. You can convect, speedcook, microwave and warm/broil. The 2 drawer fridge and freezer tuck under the quartz countertop and next to that is the combo ventless washer/dryer. Plenty of dishes, cups, pots, pans and a 3 place burner for any sized meal. This unit does not have a dishwasher.brbrIn the bathroom we have a full tile shower with a hand-held shower head. A new vanity and cabinet plus a shelf over the shower offer plenty of storage.brbrOutside we have a patio with chairs, table and umbrella to enjoy a meal or company. Cook your meal in the small charcoal grill that is provided as well. There is an outside shower and hose to spray down after your swim in the ocean and a beach cart along with chairs and other beach essentials for you to use during your stay.brbrLocation - Our property is located directly within Siesta Village on the beach side which means you are close to the restaurants and bars yet away from all the traffic on Ocean Blvd. In addition, I feel that we have the best beach on Siesta as we are located South of Big Pass and all of the marine traffic passes directly in front of you while you relax on the beach. Manatees (in the summer), dolphins, tarpon, you will see it all here and you see it in an abundance found no where else on the Gulf side of Siesta.
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Sleep 2

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$303.07

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One of our Most Beautiful Condos on Siesta Key Luxury 2BR/2BA Full Gulf Views

Siesta Key, Florida, United States

One of Our Most Beautiful Condos on Siesta Key – Luxury 2BR/2BA Gulf-Front EscapebrbrWelcome to one of our most beautiful and professionally decorated condominiums on Siesta Key. This stunning two-bedroom, two-bath residence offers over 1,200 square feet of beautifully upgraded living space and showcases the very best of coastal luxury.brbrDesigned with elegance and comfort in mind, this immaculate condo features high-end finishes, designer furnishings, and thoughtful upgrades throughout. From the moment you enter, you’ll be impressed by the light-filled open layout, refined décor, and resort-style ambiance.brbrThe spacious living area opens to a private screened lanai—perfect for enjoying Gulf breezes, morning coffee, and breathtaking sunsets. The fully equipped kitchen features modern appliances, quality cabinetry, and everything needed for preparing meals at home.brbrThe primary suite is a true retreat, offering a king bed, serene coastal décor, and a beautifully updated en-suite bathroom. The guest bedroom features two twin beds, making it ideal for children, friends, or additional guests, with convenient access to the second full bath.brbrAdditional features include high-speed wireless internet, flat-screen TVs and premium furnishings throughout.brbrLocated just steps from the world-famous white quartz sands of Siesta Key Beach, this exceptional condo places you in the heart of paradise. Guests enjoy resort-style amenities including a heated Gulf-front pool, fitness center, BBQ grilling area, BBQ grilling area, and beautifully maintained tropical grounds. Restaurants, boutique shopping, and the free village trolley are all nearby for easy exploring.brbrWhether you’re planning a relaxing beachfront escape or a memorable family vacation, this immaculate condo delivers luxury, comfort, and unforgettable coastal living.brbrBook early—this is one of our most sought-after and beautiful residences.
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Bath 2

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