Home Vacation Rentals By Owner In Siesta Key, FL

Showing 320 Of 2077 Vacation Rentals
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Exceptional(6)

$283.98

/ Nightly
Condo

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.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(11)

$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.
Bed 2

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Bath 2

Bath

Sleep 6

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Exceptional(1)

$2445.5

/ Nightly
Private Vacation Home

Siesta Key Luxe w/ Pool, Rooftop & Steps to Beach

Siesta Key, Florida, United States

Wake up to sun-soaked island days and effortless coastal luxury at Siesta Palooza, a stunning eight-bedroom retreat designed for unforgettable Siesta Key getaways. Just a short stroll from the beach, this upscale home blends resort-style amenities with relaxed island living, giving your group space to connect, unwind, and celebrate every moment together.brbrThe backyard sets the tone for vacation mode. Spend your days floating in the sparkling private pool, easing into the in-ground spa, or gathering under the covered patio with plush seating, a dining table, and grill for long, laughter-filled evenings. A dedicated game room with a TV and ping pong table adds playful energy, while the rooftop deck invites you to soak up the sun, savor the breeze, and enjoy elevated views of your surroundings.brbrInside, the home feels bright, welcoming, and thoughtfully designed for both comfort and togetherness. The main living area offers coastal-inspired seating and a large TV, perfect for movie nights or relaxed afternoons. The fully equipped kitchen is a dream for home chefs, featuring high-end appliances, generous counter space, and a large island with seating that naturally brings everyone together. Adjacent modern dining areas flow seamlessly to the deck, making shared meals and celebrations feel effortless.brbrWith eight beautifully styled bedrooms, everyone has their own retreat at the end of the day. Five king suites, including a spacious primary suite, offer comfort and privacy, while a queen room and two bunk rooms make this home ideal for families and groups of all ages. Each bedroom includes a TV, dresser space, and either an ensuite bathroom or convenient access to one. Multiple sleeper sofas add flexibility, and a washer and dryer ensure your stay stays easy and carefree.brbrUpstairs, a fourth-floor hangout space with video games and a large convertible sofa creates the perfect spot for teens, kids, or late-night lounging. Whether your group wants to spread out or come together, Siesta Palooza adapts effortlessly to your pace.brbrThe location ties it all together. Walk to nearby grocery stores, restaurants, shops, and lively nightlife, or head to the world-famous Siesta Key Beach just minutes away by foot or bike. From sunrise beach walks to sunset swims and evenings under the stars, every part of your stay feels close, convenient, and completely indulgent.brbrSiesta Palooza is more than a place to stay; it’s where beach days turn into poolside nights and memories are made without effort. Book your stay and experience Siesta Key the way it was meant to be enjoyed.brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!
Bed 8

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Bath 8

Bath

Sleep 25

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Exceptional(25)

$824.22

/ Nightly
Villa

Siesta Key 3 Bedrm, 3½ bath Villa sleeps 8 with 2900sq ft

Siesta Key, Florida, United States

Siesta Key 3 Bedroom, 3 ½ bath, 2900 Sq Ft.brWe are now offering our 3 bedroom 3 1/2 bath Villa with Wi-Fi throughout for you to enjoy your stay in Siesta Key. Just 1 block from the beach and 2 blocks to The Village makes this the perfect location for your beach vacation. Walk to the beach in under 5 minutes. Our luxurious Villa has a spacious 2 car garage. Your private elevator makes it easy to get around the house and is great for taking in groceries, luggage from the garage to all floors and up to the rooftop. The villa has high ceilings.brThe main floor has the laundry room, bathroom, kitchen, large family room, big screen TV, dining area with seating for 6 and a kitchen island that seats 6. A screened in patio is just off the kitchen with a patio table that seats 4. The kitchen has modern appliances including a wine cooler and stocked with everything you need to prepare meals or entertain.brThe 3rd floor has 3 bedrooms and 2 full bathrooms. Both guest bedrooms are tastefully decorated, share a full bathroom have queen beds, large closets and TVs with a lounge chair in the main quest room The spacious plush carpeted master bedroom features French doors to a walk-out balcony overlooking the pool, king size bed, office desk, Wi-Fi Printer, 2 large his and hers walk in closets, spacious bathroom with an oversize bathtub, granite top double sink vanity, large mirror and walk in shower.brIf you want to kick back, watch the game or hang out take the stairs or elevator to the top floor [rooftop]. Here you have a wet bar with mini fridge, microwave, ice maker, large TV, full bathroom and a couch that can fold out to a queen bed should you decide to use the room as a fourth bedroom. From here, grab a cocktail and go out on the large roof top and sit around the firepit with friends and family or relax in the lounge chairs and enjoy the partial view of the gulf and the sounds of Siesta Key.brThe pool is right off the garage door. It is heated during the winter [cool] months. Its a shared pool.br Ready to go to the beach - grab the beach buggy and load it up with beach chairs and all the toys we have available and stroll down to the beach.. When you get back there is an outside hot water shower next to the door to wash off your flip flops and the beach sand between your toes. ENJOY.br br2 pack and playsbrhigh chairbrsmall baby rocker chairbr2 baby fences brkids folding table with 2 chairsbrBeach wagon, towels, chairs and umbrella brPing pong tablebr4 bikesbrair pump on wallbrWine fridge coolerbr2 microwavesbrGas grill
Bed 3

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Bath 3

Bath

Sleep 8

Sleeps

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$2558.46

/ Nightly
Private Vacation Home

Luxury House w/ Heated Pool & Spa, Walk to Beach

Siesta Key, Florida, United States

Step into effortless island living at Point Break, a refined eight-bedroom coastal retreat where location, comfort, and resort-style design come together just moments from Siesta Key Beach and the heart of Siesta Key Village. Designed for memorable group getaways, this home places you steps from sugar-white sand, vibrant dining, and laid-back nightlife, while offering a private oasis to return to at the end of each perfect day.brbrThe backyard is your personal resort. Start mornings lounging on the sun shelf of the sparkling pool, spend afternoons floating beneath blue skies, and wind down in the in-ground spa as the evening air cools. A spacious covered patio creates an inviting setting for shared meals, casual conversation, and relaxed poolside lounging, while the adjacent game room adds energy with ping pong and foosball for friendly competition between swims.brbrInside, the main living floor is bright, social, and beautifully appointed. A vibrant, chef-inspired kitchen anchors the space with high-end appliances, abundant cookware, and a sweeping island that naturally draws everyone together. A wet bar nearby makes entertaining easy, whether you are mixing drinks for dinner or toasting the sunset. The indoor dining area offers stylish seating for group meals, while the outdoor balcony dining table extends the experience into the open air. After beach days, settle into the comfortable living room, then head upstairs to the rooftop deck to take in glowing sunsets and the gentle sounds of the island.brbrEach bedroom is thoughtfully designed to feel like a private retreat. The primary suite offers coastal charm, balcony access, and a spa-like ensuite bathroom, creating a peaceful escape. Five king guest rooms feature tropical touches, premium mattresses, and a mix of private balconies and well-appointed bathrooms, giving every adult guest space to relax in comfort. Two bunk rooms are perfect for kids or teens, offering a fun, shared layout with balcony access and a connecting bathroom. A fourth-floor bonus room with a sleeper sofa and gaming setup provides an ideal hangout space between beach adventures.brbrThe home’s layout balances togetherness with privacy, making it easy for large groups to gather while still enjoying personal downtime. An elevator adds convenience, and thoughtful details throughout ensure your stay feels seamless from arrival to departure.brbrLocation is one of Point Break’s greatest luxuries. Walk to coffee shops, grocery stores, boutiques, restaurants, and live music venues, or take a short stroll to the world-famous shoreline of Siesta Key Beach. Whether your days are filled with sun, sand, and surf or leisurely exploring the village, everything you want is right outside your door.brbrPoint Break offers the freedom to experience Siesta Key at its best, blending vibrant island energy with the comfort of a private luxury home. Reserve your stay and let your next unforgettable beach escape begin here.brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!
Bed 8

Bed

Bath 8

Bath

Sleep 24

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Exceptional(1)

$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!
Bed 1

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Bath 1

Bath

Sleep 3

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Exceptional(8)

$303.84

/ Nightly
Condo

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!
Bed 2

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Bath 2

Bath

Sleep 4

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Exceptional(11)

$255.43

/ Nightly
Condo

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.
Bed 3

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Bath 2

Bath

Sleep 8

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Exceptional(61)

$245.44

/ Nightly
Private Vacation Home

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

Siesta Key, Florida, United States

Parrot Beach Cottages Suite #4brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrParrot Beach Cottages on Siesta Key is mere steps - approximately 150 feet - from the beach and the emerald water, situated just behind the waterfront properties and within walking distance of Siesta Key Village. Occupying roughly 275-300 square feet, Suite #4 is small but fully furnished, offering one queen bedroom, a queen-size sleeper sofa, a bathroom, and a compact kitchen that can accommodate up to two adults and two small children.brbrThis suite is located on the second floor at Parrot Beach Cottages, up a flight of approximately 12 steps. It's a small space, so if you're using the sleeper sofa (which has a thin mattress and is really only suitable for small kids), you'll likely want to stow it during the day to maximize the living room. The bathroom, which has pocket doors on either side that make it accessible from both the living room and the bedroom, has a single sink, a toilet, and a shower/tub combination. On the grounds of the property, you'll also have access to a small deck that's shared with another suite, an outdoor pool downstairs, and one reserved, off-street parking space to make your stay all the more convenient.brbrParrot Beach Cottages is a two-story building that sits 150 feet from Siesta Key Public Beach Access 2, providing you with unbeatable access to one of the top white sand beaches in the world. This area of the beach is a favorite for sunbathing, swimming, romantic sunset walks, small beach weddings, skim boarding, paddleboarding, kayaking, shore fishing, and much more. Fishermen catch everything from snapper and mackerel to snook and jacks. You'll be within walking distance of a number of businesses that rent all sorts of gear, from kayaks and paddleboards to bikes and video game systems. Due to how close the complex is to the beach, several rental outfitters will bring kayaks, paddleboards, and bikes right to the property and pick them up when you're done!brbrThe suite is also within easy walking distance of Siesta Key Village, where you'll find shops, restaurants, live music, and more. Or, head into town for other local adventures, including the world-renowned Ringling Museum, the Marie Selby Botanical Gardens, Mote Marine, Jungle Gardens, and outdoor shopping and dining on St. Armands Circle.brbrThings to know:brThere are three other suites available to rent at the Parrot Beach Cottages fourplex - Suite #1, Suite #2, and Suite #3brFree high-speed WiFibrSmoke-free propertybrSmall kitchen (without a dishwasher)brBedroom is small with only a few feet on each side of the bed; no TV in the bedroombrThe suite has limited storage (one small closet)brThe shower features grab barsbrSnowbird-friendlybrPlease note that the shared pool is small, about 15 feet by 10 feet and about four to six feet deepbrThe overall property is very small, so there is no extra vehicle or visitor parking. There's also no nearby on-street parking. Guests love the location (truly walking distance to the beach and the village) and the more private feel of the beach, since this is a dead-end road and there is no nearby public parkingbrThere is a new home being built on the lot next door. Construction work is permitted by Sarasota County daily from 7:00am to 7:00pm.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 2.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 1

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Bath 1

Bath

Sleep 4

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Exceptional(3)

$353.51

/ Nightly
Condo

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!
Bed 2

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Bath 2

Bath

Sleep 6

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Very Good(1)

$269.06

/ Nightly
Condo

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.
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$734.68

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Apartment

Gertrude's Siesta | Oceanview, 12 Steps to Beach, 4min Trolley to Village, Free Gear

Siesta Key, Florida, United States

The Oceanview 603brOceanview 12-steps to Siesta Key's best beach access! Stunning views with floor-to-ceiling “movable' glass walls in master bedroom and living area. Just 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for families and couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabr brbrWhat Guests Lovebr∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windowsbr∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or nightbr∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear waterbr∙ Relaxing – safe easy access to outside attractions and lots of plus-space on sitebr∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living roombr∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinksbr∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby br∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the backbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for allbrbrThe BeachbrOur beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.brbrThe HomebrOcean view property contains just 3 units and was remodeled in 2022. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom DetailsbrThis ocean view unit is 3BR and this unit is one staircase up from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space Ask about an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrHistory – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame. brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
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Exceptional(62)

$807.53

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Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!

Siesta Key, Florida, United States

The Oceanview Penthouse 603brOceanview Penthouse, 12-steps to Siesta Key's best beach access! Stunning views with floor-to-ceiling “movable' glass walls in master bedroom and living area. Just 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for families and couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windowsbr∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or nightbr∙ It's a Penthouse –no neighbors above or next to you and best views at propertybr∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear waterbr∙ Relaxing – safe easy access to outside attractions and lots of plus-space on sitebr∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living roombr∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinksbr∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby br∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the backbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for allbrbrThe BeachbrOur beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.brbrThe HomebrOcean view property contains just 3 units and was remodeled in 2022. The penthouse unit has the best views, sun and breezes. It also doesn't share a wall or ceiling with another unit. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom DetailsbrThis ocean view penthouse unit is 3BR and is two staircases from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space Ask about an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrHistory – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame. brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
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Exceptional(13)

$1341.28

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Private Vacation Home

Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village ️

Siesta Key, Florida, United States

Toes In The Sand | Charming Siesta Key Cottage, Heated Pool, 1-Min Walk to Beach & Village Vibesbrbr Why You'll Love This HomebrThis vintage-inspired Siesta Key cottage puts you just 1 minute from the famous white sands of Siesta Beach. With a private heated pool, charming interiors, and walkable access to both the beach and Siesta Village, Toes In The Sand offers the best of Florida's coast wrapped in old-Florida charm.brbr ‍ ‍ Perfect ForbrCouples, small families, and laid-back beach lovers seeking a private retreat just steps from the shore and Siesta Key's vibrant village life.brbr ️ Imagine ThisbrYou wake up to the sound of swaying palms and distant waves. Slip on your flip flops, grab the beach caddy, and in under 60 seconds you're sinking your feet into Siesta Key's award-winning powder-white sand. After sun-filled adventures, return home to cool off in your private pool, pour a chilled drink, and settle into the Florida room as golden hour lights up the palms. At sunset, stroll to the Village for live music, fresh seafood, and tropical cocktails—all without needing a car. This is beach life, simplified and elevated.brbr Where You'll Sleepbr• Bedroom 1: Queen Bed, Ensuite Bath, TVbr• Bedroom 2: Queen Bed, Hall Bath, TVbr• Florida Room: Full Futonbrbr Explore the Areabr• 0.1 Miles (1-Minute Walk) to Siesta Key Beach Main Entrancebr• 0.3 Miles to Siesta Key Village: Restaurants, Bars, Shops & Ice Creambr• Walk to Siesta Key Village for Live Music, Waterfront Dining & Nightlifebr• Surrounded by a Bike-friendly, Pedestrian-friendly Coastal Communitybrbr⌛ Don't wait—homes this close to the beach book quickly. Your stay includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point post-stay inspection. Reserve your beach escape today and arrive at a home that feels brand new.brbr Need to Know: This pool is heated from November 15th to April 15th.
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$327.76

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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
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