Home Vacation Condo Rentals By Owner In Siesta Key, FL

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Exceptional(2)

$288.37

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Anchorage 207

Siesta Key, Florida, United States

brbrWe 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: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: QUEEN & TWIN TRUNDLEbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: 2ND FLOORbrbr- Internet Access: 4864 -0110420063brbr- Parking: Yesbrbr- Parking Space Type: OPENbrbr- View: Canalbrbr- PICKLEBALL: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr
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Exceptional(3)

$289.15

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Anchorage 208

Siesta Key, Florida, United States

brbrWe 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 Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: QUEEN & QUEENbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: 2nd Floorbrbr- Internet Access: Yesbrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: MARKED SPOTbrbr- Electric Stove: Yesbrbr- View: CANALbrbr- PICKLEBALL: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr
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Exceptional(10)

$312.08

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Florida Charm, Bayside, Pool, Tiki, Steps to Beach

Siesta Key, Florida, United States

Welcome to your own slice of paradise at our Siesta Key vacation rental, nestled within the charming Sea Club 2 complex on the shores of Sarasota Bay. As you step into this delightful second-floor condo, you'll be greeted by the tranquil ambiance of Old Florida, surrounded by lush tropical trees and vibrant plants, setting the stage for a truly rejuvenating retreat.brbrThe essence of coastal living is beautifully captured in this two-bedroom, one-bathroom condo, where modern comforts seamlessly blend with classic charm. The interior exudes a cozy coastal vibe, with furnishings in soothing shades of light gray, blues, and cream, creating a serene and inviting atmosphere throughout.brbrThe heart of the home is the open-concept living, kitchen, and dining area, where relaxation and entertainment converge effortlessly. Sink into the plush embrace of the comfy couch, loveseat, or chair as you unwind after a day of exploration, while catching up on your favorite shows on the large SMART TV.brbrMeal times become a delight in the well-appointed kitchen, boasting granite countertops and equipped with everything you need for culinary adventures. Gather around the counter with four stools, perfect for enjoying casual meals or engaging in lively conversation with loved ones.brbrRetreat to the primary bedroom, adorned with a sumptuous king bed dressed in plush linens, ensuring a restful night's sleep. A SMART TV and large light wood furniture add to the comfort and convenience, while providing ample storage for your belongings.brbrThe guest bedroom offers a peaceful sanctuary with a queen bed, SMART TV, and dresser, providing a cozy haven for additional guests or family members.brbrFreshen up in the shared bathroom, featuring a bathtub with a glass-enclosed shower door, a pristine white vanity, and fluffy towels, inviting you to indulge in a rejuvenating soak or refreshing shower.brbrOutside, the Sea Club 2 complex offers an array of amenities to enhance your vacation experience. Take a dip in the heated community pool, challenge friends to a game of bocce ball, or try your luck at fishing from the pier or boat dock. Gather with loved ones at the BBQ and picnic area for al fresco dining, or simply unwind in the hammocks or tiki hut, surrounded by the gentle rustle of palm trees and the soothing sea breeze.brbrWith its perfect blend of modern comforts, coastal charm, and idyllic surroundings, our Siesta Key vacation rental promises an unforgettable getaway filled with relaxation, adventure, and cherished memories.brbrbrSea Club 2 CharmbrExperience the timeless allure of Old Florida at Sea Club 2, a charming condominium and cottage resort nestled across from Sarasota on the Intracoastal Waterway, just steps away from the renowned Siesta Key Beach. Set amidst nearly four acres of lush palm, oak, and banyan trees, Sea Club 2 invites you to unwind in a serene and welcoming atmosphere.brbrIndulge in leisurely days basking in the sun by the heated swimming pool or seeking shade in the picnic and barbeque area. Cast your line off the fishing pier, where you might reel in snook, redfish, or jack crevalle, while marveling at passing boats and birds.brbrStroll to Crescent Beach for a day of sun-kissed relaxation or to witness the breathtaking spectacle of a Gulf of Mexico sunset. Explore the vibrant shops and restaurants of nearby Siesta Village, or embark on a day-trip to discover the myriad attractions of Florida's Gulf Coast. At Sea Club 2, every moment is infused with the timeless charm and tranquility of Old Florida.brbrThe Beauty of Siesta KeybrSiesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. brbrThe Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate.
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Exceptional(15)

$326.5

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Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach

Siesta Key, Florida, United States

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beachbr(Two Bedroom Beachfront Unit for Rent)brbrLocated Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLbrbrCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront condos are walking distance to South Village. Crescent Arms has one-story villas as well as two seven-story towers that are directly on the beach. Our vacation condos are located in the North and South Towers of the Crescent Arms Condo complex. Crescent Arms offers a picturesque serpentine pool that is secluded for your privacy and heated in winter for your comfort. The clubhouse, restrooms and showers are close by the pool for your convenience. The towers are steps from private beach access and lounge chairs are provided – already on the beach. It's not unusual to be able to watch dolphins swim by in the gulf.br brBEACHFRONT: GORGEOUS NEW LISTING - This two bedroom/two bath Crescent Arms condo - Unit 502S - is located on the fifth floor, in the south tower. Positioned in the southwest corner it has a breathtaking view of the powder white sands and the azure waters of the Gulf of Mexico. Fully furnished and decorated, this condo feature a large living room, dining area and two large bedrooms. This condo sleeps up to six (king-size in Master, Queen + twin-size bunks in the second bedroom). The beautiful screened-in Lanai has an amazing view of the Gulf and beach below. The living room has cable HD flat-panel TV. An HD flat-panel TV is also included in both bedrooms. br brThe entire unit has been renovated with beautiful hard flooring throughout. The fully equipped kitchen has granite countertops and tile backsplash with stainless steel microwave, dishwasher, glass top range/oven, and all cooking utensils, silverware and dishes. The living room has floor-to-ceiling sliders that open out onto the screened in lanai overlooking the Gulf and beach below. The living room has a leather couch and love seat and opens out to the Lanai which has a cozy table and chairs. The master bath has a granite counter and large glassed in tub/shower with modern, beautifully accented subway tile. The second bathroom has a granite countertop on vanity and a modern tiled walk-in shower.br brSunnyside Properties provides all your linens, beach towels, and ice chests. Beach chairs are provided on the beach for your convenience. We have taken great care to supply this Siesta Key vacation rental accommodation with everything you need to make your vacation a memorable success.br brAttractions and amenities within walking distance include shops, fine dining, a marina, fishing charters, jet ski rentals, boat rentals, parasailing, Dolphin Tours, intimate night clubs with dancing and free lighted tennis courts. You can avail yourself of the miles of bike/jogging paths or miles of beaches to walk on and enjoy. Over 20 golf courses are within a 20 minute drive. Across the bridge on the mainland, Sarasota and the surrounding area has unmatched cultural activities.br brSleep at night with the ocean surf right outside your Lanai windows! A laundry with washer / dryers is available for guest use, just down the hall. Of course the towers are serviced with elevators. Just 90 minutes from Tampa, two and a half hours from Orlando and Twenty-five minutes from Sarasota airport.brbrCrescent Arms is on the middle of Siesta Key on Crescent Beach. The view is to the west for spectacular sunsets!brbrNote: Rates based on occupancy of 4 - additional occupants $105/week up to max occupancy.brFor payment terms and other booking info, click here.
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$245.17

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Midnight Cove II 311F- Dreamy Beach Condo!

Siesta Key, Florida, United States

Escape the northern chill and experience the ultimate Florida retreat at Midnight Cove II 311F! This first-floor condo is perfectly situated in the heart of Crescent Beach on Siesta Key, America’s #1 beach destination. Enjoy easy access with no stairs—just a short distance from your parking spot and the private heated pool, offering options for sunbathing or shade.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis freshly updated 1,010 sq ft condo features 2 bedrooms and 2 bathrooms, a spacious kitchen and dining area, plus a cozy family room. For added convenience, you’ll find a laundry room equipped with a washer and dryer. Relax and unwind while enjoying peaceful views through floor-to-ceiling sliding glass doors that open to a small grassy area overlooking the pool.brbrTake a leisurely walk to the docks along the serene Intracoastal Waterway or stroll to the famous Siesta Key Beach via private access. Known for its powder-soft quartz-white sand, Siesta Key Beach is consistently ranked as the best in America. Discover a private beach closet stocked with essentials like chairs, toys, and a wagon for a fun day by the shore.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details).brbrExploring Siesta Key is effortless! Hop on the FREE Siesta Key Breeze Trolley to visit The Village, filled with dining, shopping, and entertainment. We’re just minutes away from downtown Sarasota and the renowned Ringling Museum of Art, and conveniently located 10 miles from Sarasota Bradenton Airport, with easy access to Orlando’s theme parks and Tampa Bay’s sports venues.brbrBook your stay at Midnight Cove II today and immerse yourself in the sun-soaked charm of Siesta Key! Your perfect vacation awaits!
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$323.45

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Gulf and Bay Club-C607

Siesta Key, Florida, United States

Gulf and Bay Club Unit C607 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit C607, a beautiful two-bedroom, two-bath condo nestled within one of Siesta Key’s most desirable gated communities. Perfect for extended stays, this vacation retreat is just a five-minute walk from the world-renowned Siesta Beach, where powdery white sand and turquoise waters await. Guests can enjoy access to a wide range of shared resort-style amenities, including sparkling pools, a rejuvenating hot tub, tennis and pickleball courts, and a fitness center.brbrHighlightsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 2 Twinsbr• 28-night minimum staybr• Less than 5-minute walk to Siesta Beachbr• Shared heated pools and hot tubbr• Tennis and pickleball courtsbr• Washer and dryer in unitbr• Shared shuffleboard, cornhole, and fitness centerbr• Convenient location near Siesta Key Villagebr• Gated community with resort-style amenitiesbrbrLocated in the Gulf and Bay Club, this condo offers access to a tropical paradise filled with everything you need for a relaxing Siesta Key getaway. Enjoy your mornings with a stroll to the soft sands of Siesta Beach or spend leisurely afternoons lounging by the heated community pools. Play a friendly game of tennis or pickleball, work out in the fitness center, or unwind in the hot tub after a day of island adventures. The complex also features shuffleboard and cornhole courts for casual outdoor fun with family and friends.brbrStep inside this bright and airy condo featuring comfortable furnishings and a welcoming open floor plan. The spacious living area includes a large smart TV and plenty of seating for cozy movie nights or quiet reading time. The fully equipped kitchen includes a refrigerator, oven, stove, microwave, dishwasher, toaster, and Keurig coffeemaker, everything you need to prepare meals with ease. The adjacent dining area provides the perfect setting for enjoying home-cooked meals or morning coffee before heading to the beach.brbrThe primary bedroom offers a peaceful retreat with a king bed, smart TV, ample closet space, and a private ensuite bathroom featuring dual vanities and a walk-in shower. The second bedroom includes two twin beds, making it ideal for guests or children. A shared hallway bathroom with a shower and tub combination provides convenience for the whole group.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbr• Second Bedroom: Two twin beds, shared hallway bath accessbrbrThis condo includes a washer and dryer, complimentary Wi-Fi, and one designated parking space. Guests also enjoy access to all community amenities, including heated pools, hot tub, tennis and pickleball courts, fitness center, and beach access.brbrWhether you’re planning a month-long stay or a winter retreat, Gulf and Bay Club Unit C607 by Tropical Sands Accommodations offers the perfect combination of comfort, convenience, and coastal charm. Enjoy resort-style living just minutes from Siesta Beach and nearby dining and shopping in Siesta Key Village. Book your extended getaway today and experience the laid-back island lifestyle that makes Siesta Key so unforgettable.
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Exceptional(108)

$485.38

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Palm Bay Luxury Resort! Private Beach, Hot Tub, Heated Pools, Tastefully Modern, Recently upgraded

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 Palm Bay Club - Bayside! brbr brbrVacation like royalty at The Palm Bay Club, one of Siesta Key’s most luxurious resorts. Enjoy private beach access, two heated pools, a hot tub overlooking the bay, tennis/pickleball courts, a fitness center, and beautifully landscaped grounds. With stunning Bay sunrises, beach sunsets, and nearby #1 rated Siesta Key Beach, this resort offers the perfect blend of relaxation and adventure. brbr brbrLOCATION HIGHLIGHTS: brbr- Centrally located on Siesta Key, close to Siesta Key Village with restaurants, boutiques, and gelato shops brbr- Access to the private beach access across the street, short drive to the #1 rated Siesta Beach brbr- Access to the Siesta Key free trolley along Midnight Pass Road and into the Village brbr- Nearby activities: Drum Circle at Sunset, water sports, biking, fishing, and beach walks brbr- Two heated communal pools, one overlooking the bay, hot tub brbr- Tennis/pickleball courts, communal grills, fitness room, communal laundry brbr- Fishing pier, boat slip rental available brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom updated 2nd floor condo (860 sq ft) brbr- Elevator and stairs access brbr- Private washer and dryer brbr- Dedicated WIFI and cable brbr- Free parking available on premise brbr brbrLIVING ROOM: brbr- Large screen TV with streamed DirecTV, DVD player brbr- Serene coastal décor with calming shades of blue brbr- Sliding doors to courtyard balcony with partial Bay view brbr- Bistro-style café table for evening drinks or relaxing brbr brbrKITCHEN AND DINING: brbr- Fully updated stainless steel kitchen, small appliances provided brbr- Solid stone countertops with ample workspace brbr- Dining table for 6, open to the living room brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, smart TV with DirecTV streaming, walk-in closet, ensuite bathroom with tub/shower combo, slider to the balcony brbr- Guest bedroom: 3 beds (1 full, bunkbed with twin on top and full on bottom), smart TV with DirecTV streaming, walk-in closet, ensuite bathroom with tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Village: restaurants from casual to fine dining, gelato shops, boutique shopping brbr- Beach & water activities: kayaking, paddle boarding, jet skis, and fishing brbr- Relax on the private beach, or rent cabanas and loungers with umbrellas brbr- Sunrise over the Bay and sunsets at the Gulf for unforgettable views brbr brbrIMPORTANT INFO: brbr- Complex rules: some units may restrict boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized vehicles; check in advance brbr- One parking space per condo brbr- No pets. No smoking brbr brbrBOOK YOUR NEXT VACATION AT THIS RESORT STYLE COMPLEX!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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Exceptional(9)

$456.42

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Stunning Views from Spacious Condo on Siesta Key!

Siesta Key, Florida, United States

Just 300 feet of powder white sand separate this unit from the crystal blue waters of the Gulf! This 2-bedroom 2-bathroom unit offers sleeping accommodations for 6. Inside, you will find a chef's kitchen with plenty of space to cook while being open to entertain guests as well. Relax on your large balcony or sit on the beach voted #1 in the USA! The unit is located in the tower, just steps away for the stunning shore! The beautifully landscaped property has a pool, grilling stations, beach chairs, and private beach access for you to relax and enjoy your time on your island getaway. Located centrally on the island, this property is perfect for experiencing the entire island. Travel to the south to the Crescent Village, or take a trip north to the Siesta Key village. Either direction you go, you’ll be surrounded by wonderful shops and restaurants, perfect for hours of endless fun. Just bring your sunscreen, bathing suit, flip-flops and have an unforgettable vacation!brbrMaster: King BedbrGuest Bedroom: 1 Queen, 1 FullbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,000
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