Vacation Condo Rentals By Owner In Siesta Key, FL

$379.86

Summer Deals! Siesta Key Hideaway at Palm Bay Club Unit #311

Siesta Key, Florida, United States

Summary:brbrBeautiful 2 Bedroom 2 Bathroom condo within Walking distance to one of the Top-Rated Beaches in the country, Siesta Key Beach and steps from the pool and private Crescent Beach. This open-concept Palm Bay Club condo on the Gulf features amenities galore! Two shimmering pools and a hot tub offer peaceful water views. Fish or watch the sunset from the charming on-site pier. Known as one of the best in America, Siesta Key Beach awaits just minutes from your door. Or check out lovely Crescent Beach in less than one mile and Lido Beach in about four miles. Red Bug Slough is a hidden gem of a park less than three miles from your door. Enjoy live music and DJs at The Beach Club, less than two miles away. Take advantage of the Siesta Key Breeze Trolley which is absolutely free! The trolley operates 7 days a week from 8am to 10pm (later on the weekends). Enjoy free rides to Siesta Key Village for shopping and dining or head south down to Turtle Beach for quieter vibes to kayak and go shelling! You can track the Trolley by downloading the Breeze Rider app on your smartphone. (Map is viewable in the photos) brbrbrbr*This unit is located on the Bay Side. You still have access to all Beachfront amenities. brbrbrbr* Direct Frontage Access to Private Beach * Two Heated Swimming pools * Large Custom Hot Tub Overlooking Serene Bay * Complimentary Fitness Center * Lighted Tennis Courts with Pickleball * Fishing Pier * Barbecue Grills * VIP Concierge Service brbrbrbrEnsuring extra privacy, this condo commands a top-floor location on the third level. Discover tasteful furnishings in every room of this bright and airy condo. An open concept living room, balcony, and gorgeous pool area offer ample space for your group. Sunlight fills the living room - gather for movie nights on the 45” TV. The pristine kitchen has everything you need to whip up vacation meals. Ample granite countertop space makes food prep easy.brbrbrbrHardwood floors shine in the primary suite, detailed with a 42-inch TV. A guest bedroom has a lively tropical vibe. Find your favorite shows on the 32-inch TV or catch up on emails at the desk. Both bedrooms have en suite bathrooms. All three TV's are connected to DirectTV!brbrbrbr15% Discount on stays of 30 days or more!brbrbrbrThings to Know:brbrSmartphone operated laundry facilities are available on-site.brbrNo pets are allowed at this vacation rental.brbrThis rental is located on floor 3 with Elevator access.brbrParking notes: There is free parking available for 1 vehicle.brbrYou must be 21 years or older to rent this property.brbr24/7 Security On-sitebrbrbrbrThe Space:brbr* Direct Frontage Access to Private Beach * Two Heated Swimming pools * Large Custom Hot Tub Overlooking Serene Bay * Complimentary Fitness Center * Lighted Tennis Courts with Pickleball * Fishing Pier * Barbecue Grills * VIP Concierge ServicebrbrbrbrGuest Access:brbrGated access to unit. You will be given code prior to check in for the gate and unit.brbrbrbrThe Neighborhood:brbrLocated in the Siesta Beach community.brbrbrbrGetting Around:brbrSiesta Key Trolley stops within walking distance and is a free service. Download the Breeze Rider App to track real-time arrivals and view maps.brbrbrbrOther Things to Note:brbrThere is 24/7 Security on site and can be reached daily after 5:00pm.brbrbrbrInteraction with Guests:brbrWhen checking in please visit the main office located across the street at 5960 Midnight Pass Rd. The office is open 7 days a week from 9:00am until 5:00pm. Office staff will give you a parking pass for one vehicle and wrist bands for each guest which will give you access to all the amenities at Palm Bay Club.

2

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2

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6

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$315.94

/ Nightly

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Anchorage 205

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 exposure bathes 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 canal. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The living room has a 50 Smart TV, and each bedroom has a 40 TV. 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: Yes (2)brbr- Balcony: PRIVATE/EXPANSIVEbrbr- BBQ Grill: Yesbrbr- Beach Access: Privatebrbr- Bed Size 1st/Master: KIngbrbr- Bed Size 2nd Rm: 2 Queensbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 2brbr- Internet Access: WIFIbrbr- Parking: Yesbrbr- Parking Space Type: Any Uncovered Spotbrbr- Electric Stove: Yesbrbr- View: SOUTHbrbr- PICKLEBALL: Yesbrbr- Bay View: Partial Bay Viewbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

2

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2

Bath

6

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$326.73

/ Nightly

Condo

Anchorage 701

Siesta Key, Florida, United States

Welcome to Seven Heaven on the 7th floor in paradise with a beautifully updated and decorated 2-bedroom and 2-bath condo. Unit 701 is located on the quiet north-side of the building with spectacular views of the gulf, bay and gorgeous sunsets!brbrInside the unit you will be greeted with travertine floors, lifted ceilings and floor to ceiling hurricane quiet patio doors. The expanded stunning kitchen has counter top seating and open to bright dining and living area. The comfortable living room has lazy boy reclining chair along with reclining couch.brbrAn extremely large master bedroom has a king size bed, smart TV, ceiling fan and reclining chair along with stunning walk-in shower with double sinks. brbrThe guest bedroom has plenty of sleeping options as well as smart TV and ceiling fan and desk workspace. One queen bed, full bed with a pull-out twin trundle providing options for everyone to have their own space. Large walk-in closet allows plenty of room for your items. Remodeled second bath has tub/shower.brbrEach room has patio doors leading to large balcony with breath taking views all around. There is a closet on the balcony loaded with everything you need to enjoy your stay; beach chairs, beach wagon, floats, coolers, beach towels (located inside), tennis racquets.brbrFireworks can be viewed from balcony on 4th of July, New Year's Eve and other random nights. Enjoy the largest pool on the Key, tennis/pickle ball, walking distance to restaurants, stores, bike rentals, etc. Hop on to the free trolley from the front driveway to the village.brbrBook your stay in Seven Heaven for your next magical stay in Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: Gas Grillbrbr- Beach Access: Privatebrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: Queen & Full & Twinbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 7brbr- Internet Access: WIFIbrbr- Walk in shower: Yesbrbr- Parking: Covered Spotbrbr- Parking Space Type: # 21brbr- Electric Stove: Yesbrbr- View: Gulfbrbr- PICKLEBALL: Yesbrbr- Gulf View: Yesbrbr- Island View: Island Viewbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

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$331.3

/ Nightly

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Beautiful Bay side Condo

Siesta Key, Florida, United States

This beautiful condo in Siesta Key is the place to be! This Beautiful fully furnished condo has one of the best views in the complex along with having one of the Best white sand beaches on the country!brOur 2-story condo has everything you need for a few days of relaxation.br2 Bedrooms each with their own bathroom, closet and Kingsize bedbr2.5 Bath brIn unit Washer/DryerbrTV in every roombrPool, Club house, and tennis court accessbrBeach Gear provided- Chairs, Towels, Games/Toys, Beach cart, Umbrella etc.brKitchen ware provided (utensils, plates, cups, pots, and pans)brIncredible view of the Siesta Key Bay and just a 10 Minute walk to the white sand public beaches!brIt's a 10-minute walk to Beach Access 12 at Stickney Point Bridge (and the famous Captain Curt's) or catch the free trolley directly out front of complex or call one of the many free rides along the Key, both of which run up and down the key all day into the night. brMain Siesta Key Beach is only about a 3–5-minute drive to the main beach parking lot where there's plenty of spaces.brAlso, a 5–7-minute drive to the village where you can enjoy the local restaurants and shops!brPlease NO pets due to allergies

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$171.48

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Upgraded 1 Bed/1 Bath Ground Flr, #1 Siesta Beach

Siesta Key, Florida, United States

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.brPlease note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.brOur condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!brOur unit has an assigned carport. brWhy just go to Florida when you can visit the #1 Beach in the USA! White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking while staying here at White Sands Village.brbrSiesta Beach: Rated 2021 #1 beach in Florida by Holidu https://www.bizjournals.com/tampabay/news/2021/06/23/siesta-key-beach-named-no-1-beach-in-the-state.html, 2020 Tripadvisor #1 beach in the USA https://www.sarasotamagazine.com/news-and-profiles/2020/08/siesta-key-beach-named-no-1-in-the-country-again-tripadvisor , Dr Beach 2017 #1 beach in the USA https://www.drbeach.org/2017-siesta-beach-sarasota-floridabrbrSORRY, NO PETS.brbrThe condo is NOT ADA ACCESSIBLE. NO SMOKING.brbrThe first sign that White Sands Village is the right place for you are the grounds, seven acres beautifully landscaped with palm trees, live oaks, flowering shrubs and tropical flowers.brOur pool is heated year-round to a warm 86º, so you can enjoy a swim even during the cooler months. Catch a bit of sun on a lounge chair, or sit in the shade and enjoy a bit of vacation reading.brPublic tennis/pickleball courts are just across the street.brFour lighted gas grills, on the White Sands property, are available for your use.brOne covered parking space is provided for each unit, with additional parking available.brLaundry facilities are available at four locations.brLinens are supplied and kitchens are fully equipped in each of our one- and two-bedroom rental units.brSit by the peaceful lagoon connected to the Intracoastal Waterway.brIn addition to the stunning Siesta Key Public Beach, there are two additional Gulf of Mexico beaches on Siesta Key, as well as great little shops and restaurants. You’ve got easy access to boat rentals, jet ski rentals, parasailing…recreation awaits you!brCrescent Beach, just south of the public beach, is a quieter and more private beach, with only one public access road. Its southern tip is the Point of Rocks, a great snorkeling and diving area with coral reefs that often harbor abundant marine life.brTurtle Beach, south of Crescent Beach, is a great family play area, with a playground, horseshoe pit, boat launch, volleyball court and picnic tables. It’s also a good place for finding shells and perhaps some shark teeth. Here you can launch your boat, fish in Blind Pass Lagoon, or eat in a nearby restaurant.brSiesta Key Village is full of shops and restaurants. You can buy just about everything you need to enjoy your beach vacation, including beachwear, sun products, and toys. There are also little boutique shops where you can indulge your love of unique clothing, jewelry, flowers and scented lotions. Several local restaurants offer patio dining, which you can enjoy from breakfast spots to dinner and evening entertainment.

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$468.19

/ Nightly

Condo

Siesta Breeze Retreat | Luxury Condo on SK w/ Heated Pool, Walking Distance to Beach & Village!

Siesta Key, Florida, United States

Siesta Breeze Retreat | Heated Pool + Steps to Siesta Key Beachbrbr Why You'll Love This HomebrWake up just 0.1 miles from the powdery white sands of Siesta Key Beach and stroll to Siesta Key Village in minutes. With a heated resort-style pool, spa, and private balconies off each bedroom, this two-story retreat blends coastal luxury with walkable convenience.brbr ‍ ‍ Perfect ForbrIdeal for couples, small families, or remote workers seeking a beachside haven with easy village access and resort-style amenities.brbr ️ Imagine ThisbrThe salty breeze brushes your face as you sip your morning coffee on a private balcony. Inside, light spills across coastal-inspired decor and open living spaces that flow from kitchen to dining to lounge. After a sun-soaked beach day just a 3-minute walk away, you rinse off and slip into the heated pool and bubbling spa, surrounded by tropical landscaping. As the sun sets, walk into Siesta Key Village for fresh seafood and music under the stars—no car needed.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Private Balcony, TVbr• Bedroom 2: Queen Bed, Shared Bath, Private Balcony, TVbr• Additional - 1 Twin Futon, 1 Twin Rollawaybrbr Explore the Areabr• 0.1 Miles to Siesta Key Beach (3-Minute Walk)br• 0.2 Miles to Siesta Key Village Shops, Dining, and Nightlifebr• Walkable Neighborhood With Bike and Golf Cart Rentals Nearbybr• Sunset Views From Nearby Beach Access Pointsbr• Enjoy Local Favorites Like The Cottage, Daiquiri Deck and Summer Housebrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr NEED TO KNOW: This home is a part of a condo unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the 1st and 2nd floors of the building, right most garage, along with the shared outdoor and pool areas. Contact us directly for more information regarding any shared space for this vacation home. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.brbrPer HOA requirements:br• Garages can fit a vehicle no bigger than 72 inches in height.br• Guest vehicle height will be needed before arrival to prevent any missed expectations or negative affects to your experience.br• One parking pad per side of the building can be used as a first come first serve basis.br• Oversized or extra vehicles to be parked on the street just outside the gates of the property.br• Grills may only be used on ground level, pulled 10 feet from the building. No grills, hibachi, or any open flame cooking device or fire pit may be used on balconies or patios.

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$283.98

/ Nightly

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Charming Siesta Key Condo With Beach Access - GBB 1318

Siesta Key, Florida, United States

Discover coastal living at its finest in this welcoming 2-bedroom, 2-bathroom ground-floor condo nestled within the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. Professionally managed by Gulf Coast Vacation Rentals, upon entry, you'll be greeted by a thoughtfully designed space adorned with coastal-inspired décor and abundant natural light. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an inviting space for relaxation and entertaining guestsbrbrStart your mornings in you private lanai overlooking the south-facing garden or take a leisurely stroll to Siesta Key Beach, known for its powdery white sand and recognized as the No. 1 beach in the USA. brbrGulf & Bay Bayside offers residents a resort-style lifestyle, with amenities such as a waterfront pool, fitness center, and meticulously maintained grounds. Embrace the coastal atmosphere as you explore the nearby Siesta Key beaches or stroll through the vibrant island community.brbrFor dining and entertainment, you're just a short walk from Siesta Key Village, where you'll find an array of unique shops, delicious eateries, and a vibrant arts scene. Gulf & Bay Club Bayside offers the ideal blend of tranquility and convenience, making it the ultimate retreat for relaxation and adventure on Siesta Key.brBook your stay now and start creating memories that will last a lifetime!brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

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$298.19

/ Nightly

Condo

Best View on Siesta Key 1 Bed 1 Bath Top Floor Steps to Beach

Siesta Key, Florida, United States

Welcome to Condo 504, a beach-themed oasis nestled in the tranquil paradise of Siesta Key Beach. Allow yourself to be transported to a world of relaxation and tranquility upon entering this one-bedroom unit located on the top floor, spanning 820 square feet. The unit provides spectacular Gulf and Beach Views, enabling you to unwind and rejuvenate.brbrThe master bedroom boasts a king-sized bed, ensuring a restful night's sleep, and a sofa sleeper is available for additional guests. Entertainment options include two TVs, free WIFI, and basic cable.brbrThe kitchen is fully equipped for meal preparation and entertaining guests. Essentials such as towels, linens, beach chairs, and umbrellas are provided, allowing you to enjoy a day at the beach without worry.brbrThe beach, located just 100 steps away, features soft white sand and breathtaking Gulf sunsets, which can be enjoyed from the screened lanai or while relaxing on the beach.brbrFollowing a day of sun-soaked fun, treat yourself to a glass of wine on the screened-in lanai while taking in the sunset. For those seeking adventure, the Village is easily accessible with the free trolley service, which provides a variety of dining, shopping, and nightlife options.brbrThe condo offers a heated pool and an on-site gym for fitness enthusiasts. Our team is dedicated to ensuring your stay is stress-free and enjoyable.brbrMake your ultimate beach vacation dream a reality by booking this condo today! Don't wait, book now before it's too late!

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Sleeps

$370.35

/ Nightly

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Professionally Decorated 2 Bed 2 Bath at Siesta Key Beach with Gulf Views

Siesta Key, Florida, United States

Beautiful views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S. can be seen from Crescent Royale's Unit 2E! This newly renovated (2024) and refurnished 2 bedroom, 2 bath condo is an end unit that features a wrap-around screened lanai that offers panoramic views of the beach and lovely sunsets. brbrThe kitchen has all new stainless steel Samsung high-end appliances, lots of cabinet storage, marble counter tops, a Keurig Single Serve K-Cup and 12 cup Carafe Coffee Maker along with smaller appliances. This Condo is equipped with wireless high-speed internet and a 75 Crystal UHD smart TV. There are 43 smart Crystal UHD TVs in both bedrooms. brbrThe public beach features lifeguards, tennis courts, volley ball, children's playground, gift shops and concessions. Free instructor led Yoga at the public beach. There is a drum circle every Sunday prior to sunset. A walk or free ride to Siesta Village is a must. There is a variety of shops, stores and restaurants with live music.

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$303.84

/ Nightly

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Gulf Views 2 Bed 2 Bath at Siesta Key Beach 100 Steps to the Sand

Siesta Key, Florida, United States

Prepare to feel regal as you step into our luxurious silver-rated condo, situated in the heart of Florida's tropical paradise. Imagine waking up to the serene sound of waves crashing onto the shore, sipping coffee while admiring the picturesque blue ocean from your window. Our condo is the perfect place to live out your dream beach vacation.brbrWith two bedrooms, two full baths, and a spacious 1220 square feet of living space, you'll have ample room to relax and unwind. The master bedroom features a plush king-sized bed, while the second bedroom offers two twin beds that can be combined to form a king bed. You won't need to worry about packing cumbersome beach gear as we've got you covered with all the essentials, including beach towels, linens, chairs, and even an umbrella!brbrThe fully equipped kitchen provides an ideal setting for preparing family meals or romantic dinners, while the screened lanai offers a picturesque location to enjoy your meal with breathtaking ocean views. After a day of soaking up the sun on the top-ranked US beach (just 100 steps away!), you can relax by the heated pool or fire up the gas grill for a cookout.brbrFor those who enjoy an active lifestyle, our resort-style complex features an exercise gym to help you stay in shape while on vacation. And when you're ready to explore, you're only a short walk away from the Village's restaurants and nightlife.brbrOur onsite management team is committed to providing excellent service to cater to your every need, ensuring your vacation is nothing short of paradise. So, pack your beach essentials and come immerse yourself in the ultimate beach vacation at our opulent Florida condo!

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Sleeps

$255.43

/ Nightly

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Near Siesta Key Beach, Renovated Updated Condo, Pools | Tennis | Gym

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers Yacht & Racquet Club 2nd FL Renovated Unit! brbr brbrExperience the best of Siesta Key from this beautifully renovated, second-floor sanctuary. Nestled directly on the Intracoastal Waterway, this spacious 3-bedroom condo combines modern interior luxury with the high-end amenities of a premier yacht and racquet club. Whether you're catching the sunrise over the marina or taking a 15-minute stroll to the world-famous white sands of Siesta Key Beach, paradise is right at your doorstep. brbr brbrRESORT-STYLE AMENITIES brbr- Aquatic Fun: Two heated swimming pools for year-round relaxation. brbr- Tennis & Fitness: Three professional-grade Har-Tru clay tennis courts, a fully equipped fitness center, and a sauna. brbr- The Marina Life: Beautiful bayfront setting with boat docks, BBQ grilling stations, and a vibrant clubhouse. brbr- Easy Island Travel: The Siesta Key Trolley stops right outside, whisking you away to the Village for dining and live music—no car needed! brbr brbrPROPERTY HIGHLIGHTS brbr- Spacious 3BR Layout: Over 1,500 sq. ft. of renovated living space, perfect for families or groups. brbr- Chef’s Kitchen: Fully equipped for vacation meal-prep with a large breakfast bar seating four. brbr- Enclosed Balcony: Accessible from the living room, offering a cozy spot to unwind after a day in the sun. brbr- Laundry & Tech: Private in-unit washer/dryer, dedicated high-speed WiFi, and cable TV in every bedroom. brbr brbrBEDROOMS & BATHROOMS brbr- Master Suite: King bed, corner windows with great light, and an ensuite bath with a spacious walk-in glass shower. brbr- Guest Bedroom 1: Comfortable Queen bed with views of the tranquil front entrance pond. brbr- Guest Bedroom 2 (The Mega-Suite): Features two Queen beds—a rare find that makes this unit perfect for kids or multiple couples. brbr- Guest Bath: Modernized tub/shower combo with sleek glass doors. brbr brbrEXTRA PERKS brbr- Beach Bundle: We provide beach chairs, an umbrella, and fresh towels so you can pack light. brbr- Parking: Includes one assigned parking space. brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach with powder-white sand and turquoise water brbr- Siesta Key Village restaurants, bars, and boutique shops brbr- Trolley rides to the beach and village hotspots brbr brbrIMPORTANT INFO brbr- Quiet & Pristine: This is a peaceful community with enforced quiet hours. No parties, smoking, or pets (including ESAs) are permitted. brbr- Parking Limits: Strictly one vehicle only. No trailers, oversized vehicles, boats, or motorized scooters/carts allowed per association rules. brbr brbrPARADISE IS CALLING - ANSWER WITH A RESERVATION ON BEAUTIFUL SIESTA KEY!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

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$126.46

/ Nightly

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Bayside Paradise on SIesta Key awaits you! Ready to relax

Siesta Key, Florida, United States

The 'Perfect Siesta Key Getaway', this Bay Oaks garden apartment is less than 1-minute walk to the pool, the fishing pier, or the waterfront BBQ grills and picnic area. Upgraded kitchen with granite countertops, dishwasher, microwave, and fully equipped kitchen opens to great room area including dining set for 4 and comfy living room area with 55 inch HDTV. Screened patio off the living room is shaded by one of the many giant oak trees. Master bedroom side has king bed, 40 inch HDTV, dresser, nightstands, and large closet; adjacent mirrored vanity area with separate toilet and full size shower room. Opposite side of condo has compact guest bedroom with queen bed, mini dresser and mini closet. No more than 4 guests and no pets allowed. Bay Oaks has tennis courts, club house with billiards, and coin laundry next to the pool. Trolley stop out front takes you to the public beach, the village, and other popular stops. You can also get to the closest beachfront (Public Access #12) a 12 min walk or 5 min bike ride; multiple restaurant, bar and shops are right there as well. The state park main beach is 8 min bike ride and the Village is about 15 min bike ride.

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$353.51

/ Nightly

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Siesta Key Beach 2BR 2 BA Corner Condo XL Lanai and Ocean Views

Siesta Key, Florida, United States

Gulf-Front Corner Condo | Chic 2BR Retreat with Sunset Views & Beach AccessbrbrWelcome to Unit 201, your private beach retreat on beautiful Siesta Key! Perfectly positioned on the second floor with an exclusive corner location, this 2-bedroom, 2-bathroom condo offers 1,210 sq ft of bright, breezy luxury—just steps from the soft white sands of the Gulf of Mexico.brbrStart your mornings with coffee and end your evenings with a front-row seat to breathtaking sunsets, all from the comfort of your coastal-chic getaway. With extra windows that invite in natural light and sea air, this unit radiates a laid-back beach vibe with upscale touches throughout. Stylish, updated fixtures ensure your stay is as comfortable as it is elegant.brbrThe master bedroom features two plush queen beds, while the second bedroom offers a king-sized escape, perfect for recharging after a day in the sun. Enjoy your favorite shows on one of three flat-screen TVs, and make use of the fully stocked kitchen to whip up everything from quick snacks to full meals. This condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon.brbrStep outside to enjoy Crescent Royale’s amenities: a heated pool, shuffleboard courts, BBQ grills, and direct beach access just beyond your doorstep. Whether you're swimming, sunbathing, or simply strolling the shoreline, you'll feel like you've found paradise.brbrTake a short walk or hop on the free trolley to explore Siesta Key Village, where you’ll find lively restaurants, boutique shops, and entertainment. Plus, an onsite management team is always available to help make your stay seamless.brbrUnit 201 is more than a vacation rental—it’s a front-row seat to Gulf Coast beauty. Book now and start making your Siesta Key memories today!

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$291.75

/ Nightly

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Siesta Key 2 Bed 2 Bath Gem Steps to the Sand and Surf

Siesta Key, Florida, United States

Welcome to Unit 102 at Crescent Royale Condominiums – a spacious 1,210 sq ft ground-floor condo offering 2 bedrooms and 2 bathrooms of beachfront luxury.brbrThe primary suite features a king-sized bed, while the guest room includes two queen beds, perfect for families or couples seeking a romantic getaway. Enjoy the feel of a private beach cottage with a screened lanai that opens to gulf views and the soft sands of Siesta Key Beach.brbrThis fully equipped unit features a modern kitchen, three flat-screen TVs, and a sleeper sofa—blending comfort with convenience so you’ll feel right at home.brbrThis condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, cooler, and a beach wagon.brbrLocated directly across from America’s #1 Beach, Crescent Royale puts you steps from the surf and just a free trolley ride away from Siesta Key Village’s dining, shopping, and entertainment.brbrResort-style amenities include a heated pool, coin laundry, fitness center, BBQ grills, and shuffleboard courts—plus an onsite team ready to help with all your vacation needs.brbrMake Unit 102 your next coastal escape—book your stay today and live the beach life!

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$269.06

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New Listing! Beachfront Luxury at Tortuga – Indoor/Outdoor Pool - 3 BDRM

Siesta Key, Florida, United States

Experience the best of Siesta Key living at Tortuga, Unit 304A, a beautifully appointed 3 bedroom, 2 bath beachfront condo offering uninterrupted Gulf views and resort-style amenities. This serene coastal retreat sits directly on the beach—just steps from the sand and surf.brbrInside, you’ll find a bright, open living space with coastal-inspired décor and floor-to-ceiling windows showcasing breathtaking sunsets. The spacious screened-in lanai extends your living area outdoors, providing the perfect spot to relax, dine, or simply watch the waves roll in.brbrThe primary suite features a king bed and an en-suite bathroom with a walk-in shower. One guest bedroom includes a queen bed, while the second guest bedroom offers a sofa sleeper with a full bed, providing flexibility for families or friends. The guest bathroom features a tub/shower combination, ideal for relaxing after a day at the beach.brbrAs a guest of Tortuga, you’ll enjoy premier amenities including a heated indoor/outdoor pool overlooking the beach, private beach access, tennis and pickleball courts, boat docks on the bay, and grilling areas. A parking garage, elevator access, a washer and dryer in the unit, and complimentary Wi-Fi & cable add convenience and comfort to your stay.brbrWake up to the sound of the waves, soak up unforgettable sunsets, and enjoy true beachfront living at Tortuga, Unit 304A—your Gulf-front paradise on Siesta Key.brbrA one-month minimum is required to stay at Tortuga. Must be the first day of the month to the last day of the month January - April.

3

Bed

2

Bath

6

Sleeps

$235.94

/ Nightly

Condo

2-bedroom condo in Siesta Key with Magnificent Gulf Views and beach access.

Siesta Key, Florida, United States

Consider this condo located on a private beach, your home away from home while you visit Siesta Key. This marvelous property features 2 bedrooms with a king bed and a 2 full beds, along with 2 bathrooms equipped with showers and hair dryers. The living room offers additional space with a cozy sofa bed for extra guests. With amenities like heating, AC, WiFi, and a fitness room, guests will have a fantastic stay. Enjoy all that Siesta Key has to offer when you stay at our place. Lanai Access from living room and bedroom with sweeping views of the Gulf of Mexico. Kitchen and bathrooms have been newly renovated. A short walk to the bustling village of Siesta Key with restaurants offering live music, cafes and boutiques.

2

Bed

2

Bath

8

Sleeps

$327.76

/ Nightly

Condo

Anchorage 804

Siesta Key, Florida, United States

A slice of paradise awaits you at this 2 bedroom 2 bathroom condominium at the Anchorage Yacht and Tennis Club on Siesta Key.brbrA private balcony off the master bedroom, a private balcony off the guest bedroom and a balcony off the main living area all provide you with magnificent views of the gulf and the Siesta Key infamous magical sunsets. Recently remodeled to provide an open concept, this condominium will be the answer to your vacation dreams. A fully equipped kitchen open to the dining area allows you to prepare meals and eat in comfort. You are also conveniently located by the Siesta Key south bridge just steps from many excellent restaurants should you choose to eat out. The master bedroom has a king size bed, an attached bathroom with a separate dressing area and a walk-in closet. The guest bedroom has two full size beds with an attached bathroom. There is a television in each bedroom as well as the main living area.brbrThe Anchorage is a gated community with private access to beautiful Crescent Beach where you can sit with your toes in the white crystal sand enjoying one of life's simplest pleasures. The Anchorage also has one of the largest heated pools on the key, an exercise room, three tennis courts, four pickleball courts, a basketball hoop, two cornhole courts and two shuffleboard courts for your enjoyment. Want to bring your boat, jet ski or kayak The Anchorage has both a floating dock for easy kayak launch and a boat dock and kayak storge rack! The Anchorage property has a park like setting on the intercoastal where you can relax and watch boats go by or fish with a fish cleaning station right there. Dolphin or manatee sightings are not uncommon! In addition, there re two gas barbecue grills and several picnic tables to enjoy a relaxing evening on the bay. The Anchorage Association frequently holds social events such as music on the bay and trivia nights to which all guests are welcome.brbrAlthough there is not a covered parking spot for your vehichle use when you stay at this condominium, cars are optional when you stay at the Anchorage. There is a FREE TROLLEY for our guests to use, right outside of our gated community to hop on.brbrYou are just steps away from many restaurants and bars offering live music and many shops to peruse for souvenirs and beach wear. In addition, there are boat rental and excursion companies across the street from the Anchorage as well as bike and beach equipment rental companies. brbrWhat are you waiting for! Come dip your toes in our white fine quartz sand! Your dream paradise vacation awaits you at Anchorage 804 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 Doublesbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 8thbrbr- Internet Access: Privatebrbr- Walk in shower: Yesbrbr- Parking: OPENbrbr- Electric Stove: Yesbrbr- View: Yesbrbr- PICKLEBALL: Yesbrbr- Gulf View: GULF VIEWbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Bed

Bath

Sleeps

$431.37

/ Nightly

Condo

Siesta Breakers #603, Gulfside in Siesta Key, FL, 6th Floor, 250 Feet from Beach

Siesta Key, Florida, United States

Thank you for your interest in Siesta Breakers #603, a 2BR-2BA, 1,265 sq. ft., 6th floor, gulfside beach vacation condominium, with a screened lanai view of the entire pool area, Crescent Beach, and the Gulf of Mexico, located in Siesta Key, FL, with the central location of the Siesta Breakers gulfside property offering many area conveniences within a few minutes walking distance, such as 8 steak and seafood houses and a full service grocery store, Crescent Beach Market with a deli counter offering both hot and cold foods, a 7-Eleven convenience store also offering both hot and cold foods and open 24 hours a day, a Pizza N’ Brew restaurant down the street, a nearby drug store and post office, courier service, stores, shops, boutiques, salons, liquor store, fine restaurants and entertainment, even a marina and various beach rental businesses and services, offering boat, kayak, paddle boards, fishing tackle, live bait, para-sailing, jet-skis, bikes, and scooter rentals, boat tours, fishing charters, and baby equipment rentals, all within 5 minute walk from Siesta Breakers, therefore the rental of a vehicle not being an absolute necessity, and the central location also offering easy access onto and off of Siesta Key.brbrFree transportation on Siesta Key is offered by Siesta Key Breeze Trolley and by Jonny’s Original Free Ride between Siesta Village to the north, and Turtle Beach to the south.brbrBeautiful views from Siesta Breakers #603, a 1,265 square foot, 6th floor, gulfside beach condo, in Siesta Key, FL at Siesta Breakers vacation condominiums, a vehicle and pedestrian gated property located directly at the end of Stickney Point Road where it intersects with the main thoroughfare, Midnight Pass Road, offering easy access onto and off this increasingly popular tourist destination, an 8 miles long barrier island just offshore of Sarasota, with the Intra-Coastal Waterway of Roberts Bay and Little Sarasota Bay on the east side, and the azure waters of the Gulf of Mexico and Crescent Beach on the west side, with some of the most beautiful, soft, pristine white quartz sand in the world. brbrThe Siesta Breakers #603 living room opens through 14 foot, floor to ceiling impact glass doors onto a screened lanai with a View of the Pool Area, Crescent Beach and the sparkling aqua blue waters of the Gulf of Mexico. The master bedroom also opens onto the screened lanai, through 5 foot glass impact doors. Enjoy the balmy breeze from the lanai with a spectacular view of the gulf, surrounded by lush tropical greenery. Guests have complete access to all Siesta Breakers property amenities, including a large heated pool, an outdoor shower, 2 tennis courts (night play available on both), clubhouse, and a private beach area (250 feet from the condo), complete with beach lounges, and chairs. The property has paver brick driveways, and parking lot, with reserved covered parking for your vehicle, and a gas barbecues available by the tennis courts. Beach access is along a walkway, just minutes to a private piece of the crystal sands of Crescent Beach. br brWiFi: brComplimentary Xfinity WiFi is available in the unit, password secured.brComplimentary Siesta Breakers Xfinity WiFi is available in the pool area and clubhouse, not password secured. brOther people might be able to see information that you send over this network if you do not have a VPN service.brbrRental Deposits:brGuest rental deposit payments received by VRBO are forwarded to the rental property owner 2 to 3 business days after receipt.brUSD $Amount (25%) Rental Confirmation Deposit Payment- Due ImmediatelybrUSD $Amount (7%) Florida State Tax- Due Immediately and held & remitted by VRBObrUSD $Amount (6%) Sarasota Tourist Development Tax- Due Immediately and held & remitted by VRBObrUSD $Amount (25%) Rental Deposit Payment Due 90 Days Prior to ArrivalbrUSD $Amount (50%) Rental Deposit Payment Due 30 Day Prior to ArrivalbrUSD $0.00 Security Deposit: Stored payment details won’t be charged or authorized to a maximum of USD $400 (for a hold on funds) by Vrbo unless the rental property owner makes a claim within 14 days of guest departure for property damage.br brCancellation Policy (non-negotiable):brTravelers who cancel at least 30 days before check-in will get back 100% of the amount they've paid. brTravelers who cancel 14-30 days before check-in will get back 50%, and after that point, they will not get a refund.br brActs of Nature Policy (non-negotiable):brIn the event of severe weather conditions (hurricanes, tropical storms, and tornados), red tide or similar poor water conditions, or any other acts of nature, COMPENSATION OR RESCHEDULING OF RENTAL ARE NOT OFFERED.brUnder Florida law, establishments are not required to issue refunds for prepaid reservations unless rental cancellation terms state otherwise.br brSevere Weather Conditions (Hurricanes, Tropical Storms & Tornados) & Mandatory Evacuations:brIn the event that the unit becomes unavailable or uninhabitable due to naturally occurring events or entities, such as severe weather conditions (hurricanes, tropical storms, and tornados), and mandatory evacuations, COMPENSATION OR RESCHEDULING OF RENTAL ARE NOT OFFERED to non-arrivals or for early departures. brAny deposits and pre-paid rent will not be refundable, so it is highly recommended that travel/trip cancellation insurance is purchased to cover financial losses from cancellations. brOfficially the Atlantic Hurricane season is June 1 to November 30th. However, the most probable time for hurricanes is from mid-September to mid-October.br brRed Tide or Similar Poor Water Conditions:brIn the event that during your stay there is an occurrence of red tide, or red tide is present upon arrival, COMPENSATION OR RESCHEDULING OF RENTAL ARE NOT OFFERED to non-arrivals or for early departures.brNo compensation or rescheduling of rental are offered for the inconvenience of red tide or similar poor water conditions on Crescent Beach in Siesta Key, or the surrounding areas.br brTravel Insurance (recommended):brWe strongly advise and encourage guests to purchase travel insurance for protection in case they have to cancel their reservation due to an impending storm, hurricane warning, mandatory evacuation, or other unforeseen and unexpected events, as our cancellation policy is non-negotiable.br brReasons for Siesta Breakers #603 Rental Appeal:brSiesta Breakers #603 over the years has become a very popular condo rental unit with an 15 year average occupancy rate of 74.9% and a returning guest rate of 52.3%, and for many obvious reasons: br br1) Comprehensive Arrival & Departure Information Package provided to guests 30 days prior to their arrival to give an advance opportunity for guests to begin planning their Florida sun vacation activities.br2) Area conveniences available within a few blocks walking distance from Siesta Breakers #603 because of the Central Location of the Siesta Breakers property on Crescent Beach, consisting of 18 assorted restaurants, cafés and eateries, 8 rental businesses, 2 liquor stores, 4 shops, 2 salons, convenience store, real estate agent, drug store, post office, florist, and a courier service. br3) Resort Amenities available to Guests at Siesta Breakers. br4) Ease of Access to and from the Siesta Breakers property.br5) Siesta Breakers is a Gated Property with a security access code required for vehicle entry, and pedestrian entry from the street, and from the beach.br6) Complimentary Poolside WiFi is available to guests at Siesta Breakers. br7) Wheelchair Access to the pool area & Crescent Beach. br8) Siesta Breakers has a Power Failure Generator which will switch on during a power failure, and maintain lighting and elevator operation only. You must turn off the A/C during a power failure, and must not use the stove or the dryer.br brSiesta Breakers #603 At-a-Glance Look-Up:brAlarm Clock Radios (2)brBlender & Hand MixerbrCeiling Fans (3), A/C & Heating brDishwasher brDrip Coffee MakerbrDVD & VCR PlayerbrFull Kitchen brImpact Sliding Glass Doors brIron & Ironing BoardbrLinens & Towels brRange / Oven / OTR MicrowavebrRefrigerator / Freezer / Ice MakerbrStorm Door with ScreenbrTableware, Glasses & Cooking UtensilsbrTelephones / Answering Machine (3 cordless)brToasterbrTV’s (2) & Cable brVacuum CleanerbrWasher & Dryer br brSiesta Breakers #603 Property Details:brA/C & Heating: CentralbrArea: 1,265 Feet2 / 120M2brBathrooms: 2brBedrooms: 2 brBeds: 2 Queen & 2 TwinbrElevators: YESbrLanai: Screened (with accessed from living room and master bedroom)brLevel: 6th FloorbrLocation: GulfsidebrMaximum Capacity: 6 brMinimum Stay: 7 Nights (Saturday to Saturday Only) brPets: NO PETS ARE ALLOWED IN THE UNIT OR ON THE PROPERTY brRV's, Trucks, Boats, Trailers, Motorcycles, or Motor Scooters: NOT ALLOWED ON THE PROPERTY brSliding Glass Doors: Impact glass (floor to ceiling in the living room and standard size in master bedroom)brSmoke Alarm: CentralbrSmoking: NO SMOKING IS ALLOWED IN THE UNIT brStandard Occupancy: 4 brType: CondominiumbrView: Gulf of Mexico, Crescent Beach & Pool AreabrWasher & Dryer: YESbrWheelchair Accessible: YES brProximity to:brCrescent Beach: 250 Feet brSiesta Beach: 1.3 MilesbrTurtle Beach: 2.6 MilesbrSiesta Key Village: 3.1 Miles, 8 Minutes by Car or 59 Minutes Walking Along the BeachbrLongboat Key: 13 Miles

2

Bed

2

Bath

6

Sleeps

$215.19

/ Nightly

Condo

Welcome to Siesta Dreams at Casa Mar!!

Siesta Key, Florida, United States

Welcome to Siesta Dreams at Casa Mar! This 1br/1ba fully equipped condo is perfect for your next beach vacation! This location requires a minimum one week stay.br Enjoy the resort's private beach in the provided lounge chairs while you dig your toes into the quartz sand. Need a break from the salt water Take a swim in one of two pools on the property instead. Shuffleboard, tennis, or pickleball interest you We've got it! The serene tropical vibe of this community is one you won't want to leave. The condo itself is well appointed with all the necessities. A king size bed in the bedroom, and sleeper sofa in the living room allow for up to 4 guests.

Bed

Bath

Sleeps

$314.44

/ Nightly

Condo

Gulf Holiday unit 8!!

Siesta Key, Florida, United States

Gulf Holiday Unit 8 by Tropical Sands Accommodations brbrWelcome to Gulf Holiday Unit 8, a recently refreshed one bedroom, one bathroom condo perfectly located in the heart of Siesta Key Village and just a two-minute walk to Siesta Key Beach. Ideal for couples or small families, this cozy and budget friendly Siesta Key vacation rental offers updated interiors, comfortable sleeping options, and easy access to dining, shopping, and island transportation. With the beach, village attractions, and trolley stop all within walking distance, this home delivers a convenient and relaxed island getaway. brbrHighlights br• 2-minute walk to Siesta Key Beach br• 1 bedroom / 1bathroom br• 1 king bed and 1 queen sleeper sofa br• Recently refreshed interior br• Community pool br• Shared washer and dryer access br• 1 assigned parking space br• Walk to Siesta Key Village dining and shopping br• Near Siesta Key Breeze Trolley stop brbrGuests at Gulf Holiday enjoy access to a community pool, shared laundry facilities, and beautifully maintained common areas. The central location allows you to walk to restaurants, cafes, boutiques, live music venues, and ice cream shops throughout Siesta Key Village. The nearby Siesta Key Breeze Trolley offers free island-wide transportation, making it easy to explore without relying on a car. brbrInside, the condo features bright coastal decor, and an open living area designed for comfort. The living room includes cozy seating, a smart TV, and a queen sleeper sofa, offering flexible sleeping space for additional guests. The kitchen is fully equipped with essential appliances, cookware, dishware, and utensils, making it easy to prepare simple meals, morning coffee, or beach day snacks. A dining nook provides a convenient space for meals or planning your day on the island. brbrThe private bedroom offers a peaceful retreat with a king bed, soft linens, storage space, and a calming coastal atmosphere for restful nights. The bathroom includes a walk-in shower and single vanity, providing everything needed to refresh after a day at the beach or pool. brbrRoom Details br• Primary Bedroom: King bed br• Living Area: Queen sleeper sofa brbrGuests enjoy WiFi, TV access, assigned parking, shared washer and dryer facilities, and proximity to both the beach and Siesta Key Village. Nearby activities include swimming, biking, boating, parasailing, fishing, snorkeling, and sunset watching, all part of the Sarasota coastal lifestyle. brbrWith its unbeatable location near Siesta Key Beach and Village, updated interior, and convenient community amenities, Gulf Holiday Unit 8 by Tropical Sands Accommodations offers a simple, comfortable, and affordable way to experience one of America’s most loved beaches. Book your stay today and enjoy the laid back island lifestyle of Siesta Key! brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind.

1

Bed

1

Bath

4

Sleeps

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