Vacation Condo Rentals By Owner In Siesta Key, FL

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWELCOME TO JAMAICA ROYALE TOWNHOME #3 brbr brbrLocated in the sought-after Jamaica Royale beachfront complex, this fully renovated, updated two-story townhome combines comfort, convenience, and direct access to world-class amenities. Just a 30-second walk to the heated pool and private beach, it’s the perfect retreat for those looking to relax and recharge on Siesta Key’s famous white sand. brbr brbrPROPERTY HIGHLIGHTS brbrPrime location just steps to Jamaica Royale’s private beach and heated pool brbrPeek-A-Boo Ocean Views: Relax on your private balcony with partial views of the Gulf. brbr2 bedrooms and 2 bathrooms, accommodating up to 6 guests brbrMaster suite with king bed, TV, and enclosed lanai overlooking lush courtyard greenery brbrGuest bedroom with queen bed, flat-screen TV, and ample storage brbrSpacious living room with sleeper sofa, Smart TV, and private outdoor patio brbrFully equipped kitchen with granite counters, stainless steel appliances, and all cooking essentials brbrIn-unit washer and dryer for guest convenience brbrUncovered parking included brbr brbrSLEEPING ARRANGEMENTS brbrMaster Bedroom: King bed + private enclosed lanai brbrGuest Bedroom: Queen bed brbrLiving Room: Queen sleeper sofa brbrSleeps up to 6 guests brbr brbrINSIDE THE TOWNHOME brbrGround floor features an updated kitchen, cozy dining area, and open living room with beach-inspired décor brbrPrivate outdoor patio for lounging or dining after a day at the beach brbrUpstairs, master suite with enclosed lanai perfect for morning coffee or evening wine brbrGuest room designed for comfort with modern finishes and plenty of space brbr brbrRESORT AMENITIES brbrThree heated swimming pools brbrGas BBQ grills and outdoor dining areas brbrShuffleboard courts brbrPrivate beach access just steps away brbr brbrLOCATION brbr1.5 miles to Siesta Key Village with boutique shops, dining, and entertainment brbrFree local ride services available to the Village and nearby attractions brbrEnjoy favorites like Meaney’s Mini Donuts, Big Olaf’s Ice Cream, and fresh seafood restaurants nearby brbr brbrADDITIONAL DETAILS brbrSleeps up to 6 guests brbrBeach gear included for your use brbrNon-smoking and pet-free property brbrCovered parking provided (please confirm vehicle restrictions before booking) brbr brbrBOOK YOUR STAY AT JAMAICA ROYALE TOWNHOME #3 TODAY brbr brbrEnjoy two stories of modern comfort, private beach access, and all the amenities you need for an unforgettable Siesta Key getaway.brbrNext door complex is under construction. Unfortunately, we don't have any say in the matter.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.

Steps to Sand & Peek-A-Boo Ocean Views: Refreshed Jamaica Royale Townhome with Pool and Comforts!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$287.32

Retreat to the Gulf Coast and capture the essence of bayside living when you stay at this 4-bedroom, 3-bathroom Siesta Key vacation rental! Boasting an enclosed lanai and access to community amenities, this coastal condo will be perfect to return to after a fun-filled day. Sip a cup of coffee with beautiful views of the bay before enjoying a day at Siesta Beach. Take the kids to the Mote Marine Aquarium to touch the stingrays, or take a day trip to Tampa and experience thrills at Busch Gardens!brbr-- THE PROPERTY --brbrCND6804950 | Community Amenities | Walk to Siesta BeachbrbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Twin DaybedbrbrCOMMUNITY AMENITIES: Outdoor pool (depth 4’-6’), gym, 3 Har-Tru clay tennis courtsbrINDOOR LIVING: Enclosed lanai w/ bay views, 3 Smart TVs, flat-screen TV w/ cable, dining table, board games, walk-in showerbrKITCHEN: Electric stove, Keurig & drip coffee makers, dishwasher, microwave, toaster, cooking & dining basicsbrGENERAL: Free WiFi, central heating & A/C, linens/towels, washer/dryer, complimentary toiletries, hair dryerbrSUITABILITY: Step-free access via elevator, 2nd-floor unitbrPARKING: Reserved covered parking (1 vehicle)brbr-- THE LOCATION --brbrFAMILY FUN: Crescent Beach (0.8 miles), Siesta Key Beach (0.9 miles), Siesta Key Drum Circle (0.9 miles), Sarasota Beach (1.4 miles), Point of Rocks (1.9 miles), Sarasota Jungle Gardens (10.0 miles), Mote Marine Laboratory & Aquarium (10.8 miles), Busch Gardens Tampa Bay (81.3 miles)brHIT THE LINKS: Tournament Players Club Prestancia golf course (6.1 miles), Village Green Golf Club (6.3 miles), Stoneybrook Golf and Country Club (6.7 miles), Serenoa Golf Club (9.3 miles)brWALKS & HIKES: Phillippi Estate Park (3.1 miles), Red Bug Slough Preserve (4.4 miles), Marie Selby Botanical Gardens (6.3 miles), South Lido County Park (10.6 miles)brAIRPORTS: Sarasota-Bradenton International Airport (11.5 miles), Tampa International Airport (63.5 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: There is construction ocucring on the exterior of this property, and may cause noise during your stay

Breezy Siesta Key Condo w/ Bay Views & Pool!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$294.88

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 2 bedroom, 2 bathroom, private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer.brbrAnchorage Resort Condobr2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Intracoastal WaterwaybrSecond Floor Condo in the peaceful treetopsbrFully equipped Kitchen with seating for 6 at the dining tablebrBeach Supplies include- Chairs, Cooler, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbr25-year minimum age to rent restrictionbrbrBEDROOMS (Second Floor Condo)brBedroom 1: One King Bed (Attached Bathroom) 42 TV / Balcony AccessbrBedroom 2: Two Doubles Beds (Attached Bathroom) 32 Smart TV / Balcony AccessbrbrPool Information:br- Community Poolbr- HeatedbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each Floorbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brThis is an industry-standard practice.brbr FOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 2nd Floor 2 Bedroom Condo Facing IntraCoastal Waters

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$286.08

Get ready to soak up the sun and surrender to the ultimate beachside escape! This third-floor 2 BR 2 BR condo will have you feeling like royalty with its stunning view of the Gulf of Mexico's pristine beaches. It's a year-round oasis where every moment will take your breath away!brbrThe open design of this condo is like a warm hug, complete with three flat-screen TVs and free WIFI to keep you entertained. The master bedroom is fit for a king, with a posh king-sized bed, while the guest room is a cozy haven with a queen-sized bed. For an extra guest, there's a sleeper sofa that's perfect for a lazy afternoon snooze.brbrThe fully-equipped kitchen is a chef's dream, with modern appliances that make meal prep a breeze. And talk about convenience and comfort! Easy elevator access and proximity to the laundry room means you can spend more time enjoying the beach.brbrSpeaking of the beach, you're only a hop, skip, and jump away from Siesta Key Beach that's been named Number One Beach in America. And if you want to explore beyond the beach, take a short free trolley ride to The Village where you'll find ample dining, shopping, and nightlife options.brbrBut let's not forget about the condo's amenities that will make you feel like royalty. Take a dip in the heated pool, work out in the fitness center, or enjoy a barbecue in the designated areas. And the views from the lanai are absolutely stunning, making it the perfect spot for your next Instagram post.brbrEscape to Unit 310 at Crescent Royale for a peaceful getaway that'll leave you feeling rejuvenated. Our onsite management team is available 24/7 to ensure your Siesta Key experience is unforgettable. Book with confidence and get ready for the beach retreat of your dreams!

Panoramic Gulf Views 2 Bed 2 Bath at Siesta Key Beach Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$291.75

Welcome to your exclusive end unit retreat at Siesta Beach, where sun, sand, and luxury await! Nestled on the shores of the award-winning Siesta Beach, renowned for its dazzling white sands, this stunning beach rental offers an unparalleled vacation experience.brbrStep inside this meticulously crafted beach haven and discover two spacious bedrooms, each boasting its own en suite bath for added convenience and privacy. The heart of the home is a sunlit living and dining space offering breathtaking views of the beach and the serene sounds of the ocean waves. With a glass or screen enclosed lanai as your private retreat, every sunrise and sunset becomes a cherished moment to cherish and savor. Whether you're starting your day with a tranquil coffee or ending it with a captivating sunset, the lanai provides the perfect setting to connect with the beauty of Siesta Beach and create memories that will last a lifetime.brbrRecently renovated to the highest standards, this beachfront gem features luxury vinyl plank flooring, state-of-the-art Whirlpool stainless steel appliances, nespresso machine and frother, nutri bullet blender, white cabinets, granite counter tops, new king mattress, and a Halo whole house air filtration system to ensure your comfort and well-being. Every inch of this retreat has been thoughtfully designed, from the fresh paint to the stylish furniture and decor, creating a modern and inviting ambiance.brBut the luxury doesn't end there! Step outside and indulge in a wealth of amenities, including a sparkling pool, a well-equipped fitness center, and outdoor grills perfect for al fresco dining. Beach chairs and an umbrella are provided for your convenience, allowing you to relax and soak up the sun in style.brbrLocated just a short stroll from the vibrant Siesta Key village, where you'll find an array of shops, restaurants, and entertainment options, this beach rental offers the perfect blend of convenience and luxury. And with a free trolley available to whisk you away to explore the island's treasures, your dream vacation awaits at Siesta Beach. Book your stay today and experience the ultimate beachfront getaway!

Siesta Key Beachside Corner Unit 2 Bed 2 Bath Beach and Gulf Views

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$297.8

Welcome to paradise at Crescent Royale, where world-famous Siesta Beach is just 100 steps from your door. Condo 311 is a spacious 2-bedroom, 2-bathroom getaway offering more than 1,220 square feet of open living space and panoramic Gulf views. Start your mornings on the screened lanai with a cup of coffee as the sun rises and the beach comes to life.brbrCrescent Royale offers the perfect coastal retreat, complete with beach-facing suites, a heated pool, and an inviting outdoor area ideal for relaxing, grilling, or gathering with family and friends.brbrInside Condo 311, the screened lanai provides a stunning view and a peaceful place to unwind. The living room features a 50-inch flat-screen TV, and both bedrooms include their own flat-screen TV and full bath for added comfort and privacy. The guest bedroom can also be converted to a king bed. Complimentary Wi-Fi and Netflix are included for your convenience.brbrWe provide all the essentials for a carefree stay, including linens, towels, beach chairs, and umbrellas. Just bring your swimsuit, flip-flops, and sunscreen.brbrPicture yourself waking up to the Gulf breeze, coffee in hand, with a box of Meaney’s Mini Donuts ready for the perfect beach morning. Take a stroll along Siesta Beach, spend the day soaking up the sun, then return home to enjoy a cool drink on the lanai as the sunset fills the sky with brilliant shades of orange. Prepare a meal in the fully equipped kitchen, grill poolside, or head to Siesta Key Village to enjoy one of the many local restaurants.brbrHosting a family gathering or special event Our rental staff can reserve the community room, which accommodates larger groups and includes its own kitchen.brbrWith its unbeatable location, beautiful views, and thoughtful amenities, Condo 311 is the perfect place to experience the best of Siesta Key

Siesta Key Beach Paradise 2 Bed 2 Bath with Full Gulf Views Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$357.1

Get ready to soak up some serious rays in our beachy haven, Condo 3D, located in the paradise of Siesta Key Beach! With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, you'll have plenty of room to stretch out and catch some Z's.brbrThis beach-themed unit will transport you to a world of tranquility, with a master bedroom offering a king-sized bed that will have you snoozing soundly, and a guest room with twin beds that can also be joined together. You can also kick back on the sleeper sofa in the living room. The unit also comes with 3 flat screen TV’s. brbrHungry The kitchen has everything you need to whip up a feast or entertain guests.brbrOf course, the real star of the show is the beach! The condo is only 100 steps away from the soft white sand, and you can catch breathtaking views of the famous Gulf sunsets from the screened lanai or while unwinding at the beach.brbrForget about lugging around your beach gear - we've got you covered! Our condo is fully stocked with towels, linens, beach chairs, and even umbrellas. All you need to bring are your beach essentials, like a swimsuit, shades, sunscreen, and flip flops.brbrWind down your day of sunbathing and sandcastle-building by sipping some vino on our screened-in lanai, admiring the sunset. If you're feeling adventurous, hop on our free trolley to explore the Village, where you'll find plenty of dining, shopping, and nightlife options.brbrFor those fitness fanatics, you can keep your beach bod in shape with our beach-facing suites, heated pool, and on-site gym. Our team is dedicated to making your stay as stress-free and enjoyable as possible.brbrThis condo is the ultimate beach vacation dream - all you need to do is book it to make it a reality!

Beachy 2 Bed 2 Bath at Siesta Key Beach with Full Gulf Views Walk to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$302.49

Get ready to uncover Siesta Key’s hidden gem - Condo 400. This beautiful fourth floor end unit boasts a jaw-dropping panoramic view of the Gulf of Mexico. Imagine watching the gorgeous Siesta Key sunsets from the lanai as well as from the bedrooms. It’s truly a sight to behold. With a slightly larger floor plan of over 1260 square feet, you’re in for a treat.brbrThis condo is a beach-lover's paradise, with its cool beachy vibe, matching the pristine blue water and white quartz sand. The Master bedroom is fitted with a plush king-sized bed and both full bathrooms have recently been updated, along with new flooring and furniture in the unit.brbrIf entertainment is your thing, then you're in luck! With a 55 Smart TV and an additional 48 in the Master Bedroom, you're all set for movie marathons. Oh, and did we mention the complimentary WIFI for your streaming pleasure brbrLocated centrally in Siesta Key, Crescent Royale is the perfect spot for anyone who loves to explore. You can catch a free trolley or walk to The Village, where there's a ton of dining, entertainment, and shopping options. There's something for everyone!brbrAs if that wasn't enough, our community amenities are sure to make your stay even more enjoyable. You'll have access to a heated pool, workout gym, BBQ area, and shuffleboard court.brbrBut the best part You are steps away from the World famous Siesta beach. No parking worries for you! Enjoy the beach, the blue/green waters, and most of all the sunsets. There is nothing more peaceful. If you need anything, our onsite management team is always available to make sure your beach vacation runs without a hitch. So, what are you waiting for Book Condo 400 today, and thank us later!

Gulf and Beach Views Galore 2 Bed 2 Bath at Siesta Key Beach Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$303.84

Welcome to your luxurious vacation home at the Crescent Royale Condominiums, located in the beautiful Siesta Key! Unit 4C is a newly renovated 1220 square foot beachfront condo that will leave you breathless. With two cozy bedrooms, two full bathrooms, and a double-wide lanai, you'll be able to soak up the world's most stunning sunsets over America's number one rated beach in no time.brbrThis high-end beach pad is fully equipped with all the top-of-the-line amenities. From porcelain plank flooring and granite countertops to crown molding, solid core doors, and more, no expense has been spared. The fully-equipped kitchen features stainless steel appliances, and the new dry bar includes a dual-zone beverage cooler to keep your drinks chilled. The living room is equipped with three wall-mounted flat-screen TVs and a DVD player.brbrThis beachside paradise is just steps away from the sand, and we've got you covered with all the beach gear you'll ever need, from chairs and umbrellas to coolers, toys, and floats. The complex boasts one of Siesta Key's largest pools, perfect for barbecues and lounging in the sun. Take a stroll down to Siesta Key Village, where you'll find the best nightlife, restaurants, and shopping.brbrAt sunset, the views from your giant lanai will leave you speechless. Crescent Royale offers a heated pool, a workout gym, a BBQ area, and a shuffleboard court. Our team is always on hand to help, should you need anything. This unit is highly sought after, so book now and experience the ultimate Siesta Key dream. We love it, and we're confident you will, too!

Siesta Key Full Gulf Views 2 Bed 2 Bath Stunning Condo Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$303.84

Step into the grand Condo 307 at Crescent Royale and prepare to be wowed! This slice of paradise flaunts a massive 2-bed, 2-bath floor plan that sprawls over 1225 square feet. Kick back and relax in style in this spacious abode, perfect for entertaining or just lazing around.brbrThe main bedroom is a scene straight out of a royal palace, with a king-sized bed fit for a king, while the second bedroom boasts a queen and a full bed, giving everyone space to snooze. The kitchen has everything you need to whip up a culinary storm, and every room has a smart TV for your viewing pleasure.brbrThis condo is the perfect blend of beachside grace and modern glam, making it the ultimate destination for those who crave both comfort and luxury. Oh, and there's more! Take a trolley ride or a nice stroll to the Village and enjoy some old Florida charm, with endless options for dining, shopping, and nightlife.brbrWant to relax without leaving the condo No problem! Enjoy amenities like a heated pool, fitness center, and BBQ areas. But wait, the best part is yet to come! Bask in the breathtaking views from the screened-in lanai and capture the perfect Instagram-worthy sunset shot that you'll remember forever.brbrWhether you're planning a romantic getaway or just a peaceful retreat, Condo 307 at Crescent Royale is the place to be. With our friendly on-site team available 24/7, you can book with confidence and know that your ultimate Siesta Key Beach vacation experience is just a few clicks away!

Steps to the Beach 2 Bed 2 Bath at Siesta Key with Full Gulf Views

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$350.5

This 2-bedroom, 2-bathroom condo is the perfect place to take your next vacation! With a king bed in the Master bedroom, two full beds in the second bedroom, and a twin pullout ottoman , this condo can comfortably sleep up to 7 guests. You will be amazed by the breathtaking views of the Gulf from the wrap around balcony! This unit is on the 5th floor, accessible by stairs or elevator. This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Right across the street is our world-famous Siesta Beach, and just minutes away is Siesta Key Village, offering endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1- KingbrBedroom 2- Two Full BedsbrLiving Room- One Twin Pullout OttomanbrbrAdded 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

Lovely 2 Bedroom/ 2 Bath Across Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$279.16

Enjoy the ultimate Siesta Key getaway with top-notch amenities, a prime location, and a beautifully furnished condo designed for comfort and relaxation! Directly across the street to Crescent Beach on Siesta Key, this lovely condo also offers tennis and pickleball courts, heated pools and a fitness center. brbrResort-Style Amenities:br• Prime location in Gulf and Bay Club Bayside, one of Siesta Key’s most popular vacation communities.br• Two heated swimming pools surrounded by tropical landscaping, perfect for relaxation.br• Fully equipped fitness center.br• Tennis and pickleball courts for fun and competitive matches.br• Private beach access to world-famous Siesta Key Beach, just a short walk across the street through the Gulf and Bay Club Condominiums.br• Free Siesta Key trolley stops nearby, offering easy transportation to Siesta Key Village, where you’ll find an array of shops, restaurants, and nightlife.br• Lush, well-manicured grounds with walking paths, a fishing dock, and scenic water views.br• Gated community with secure parking and additional guest parking.brbrCondo Interior and Features:br• Beautifully furnished with a beachy vibe, featuring tropical hues of turquoise and light green.br• Spacious open living area with plush seating, a flat-screen TV, and glass sliders leading to the screened-in lanai.br• Lanai with outdoor dining table and chairs, perfect for morning coffee or sunset meals.br• Large, fully equipped kitchen with granite countertops, stainless steel appliances, and ample cabinet space.br• Primary bedroom suite with a king bed, flat-screen TV, and a private ensuite bathroom.br• Primary bathroom with a walk-in glass shower, large vanity, and plush towels.br• Additional sleeping spaces:br-Queen sleeper sofa in the living room for extra guests.br-Small sleeping nook with two twin beds and an accordion door for privacy—perfect for small children.br• Guest bathroom with a tub/shower combination, vanity, and a stacked full-size washer and dryer.br• Pack light – we’ve got you covered with beach chairs, towels, and an umbrella for your seaside adventures.brbrGulf and Bay Club BaysidebrGulf and Bay Club Bayside is a premier vacation community on Siesta Key, offering resort-style amenities in a lush tropical setting. Guests enjoy two heated pools, tennis and pickleball courts, and a fully equipped fitness center. The community provides direct access to the Intracoastal Waterway, perfect for fishing and wildlife watching. BBQ areas offer a great spot for outdoor dining. A short walk across Midnight Pass Road leads to private beach access on world-famous Siesta Key Beach. With stunning scenery and top-notch amenities, Gulf and Bay Club Bayside is the ideal destination for a relaxing and memorable beach getaway.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.brbrPLEASE NOTEbr----------------------------br• Prior to arrival Guest needs to complete the Bayside HOA Online Registration Form here: https://form.jotform.com/233455309537056br• Upon arrival, for your Parking Permit, please enter through the main gate and visit the onsite office at 1200 Siesta Bayside Drive. You will need to sign and acknowledge the Property Rules and Regulations. Please return the parking permit to the office upon departure or additional fees may apply. br• Beach Access: Please review the map in the front office to ensure you use the correct deeded route to the beach. Guests cannot walk through the carports for beach access. Thank you for your cooperation and understanding!br• Fobs/Wristbands: Two fobs and 4 wristbands are provided in the condo. Please note there is a $60 replacement fee for fobs and a $10 replacement fee for wristbands. Please be sure to keep these safe, dry, and sand-free and return to the unit for our next guests. Any missing fobs or wristbands will be charged to your account per your rental agreement. Thank you for your understanding and we look forward to hosting you! Please contact us with any questions.

Gulf & Bay Club Bayside | Walk to Beach, Enjoy Pools, Tennis & More

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$417.74

Newly fully luxuriously decorated beach Townhouse is just a few steps from the private white sandy US #1 rated Siesta Key Beach. This 2 bedroom 2.5 bath is everything you want and more! It will exceed your expectations. Look no further

Super Clean | private beach |amenities | location

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$230.05

Your perfect vacation awaits in this Two Bedroom, One Bath Condo - directly across from famous Siesta Key Beach, always included in the world's top ten best beaches. The apartment also offers you easy access to Siesta Village which has numerous restaurants, specialty shops, night life and other attractions.brbrUnit 216 is appointed in modern seaside decor and overlooks the pool. With a king bed in the master bedroom, two twin beds in the guest room and sofa in the living room this unit sleeps up to six people. The kitchen features a dining set convenient for enjoying a night in and the unit is turnkey furnished with all the amenities you need to make your stay fun and relaxing. The screened in lanai is perfect for enjoying your breakfast outside or taking in the cool night time ocean breeze. Come and sink your toes into the powdery, white, sugar sand just steps from your own front door here at La Siesta Condominiums.

Cozy 2-bedroom condo in Siesta Key - right across the street from the beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.54

Experience the ultimate beach escape at Unit 110, just steps away from Siesta Key Beach's dazzling, white quartz sand.brbrThis 2-bedroom, 2-bathroom unit offers approximately 1,250 square feet of charming living space. Upon entry, you'll be welcomed by a cozy living and dining area that flows seamlessly into a screened lanai providing stunning sunset views delivered to you by nature.brbrThe master bedroom features a comfortable king-sized bed, while the second bedroom offers two twin-sized beds, providing ample space for 4 guests. brbrThis condo also includes beach equipment for your convenience: beach chairs, a beach umbrella, beach towels, and a beach wagon.brbrLocated within strolling distance or a complimentary trolley ride to The Village, this unit offers convenient access to the iconic destination, brimming with delectable restaurants, unique shopping spots, and a bustling ambiance that's perfect for people-watching. Whether you're indulging in the powdery sands of Siesta Key Beach, or taking a refreshing dip in the heated pool, this unit is ideally situated.brbrBook today and create unforgettable memories!

Steps to the Sand 2 Bed 2 Bath Siesta Key Condo with Gulf Views

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$306.09

Jamaica Royale 108 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 108, a beautifully remodeled two-bedroom, two-bath villa in the heart of Siesta Key. Just a five-minute walk from the world-famous Siesta Beach, this modern coastal retreat offers an open-concept layout, fresh tropical decor, and access to outstanding resort-style amenities. Perfect for families or small groups, this villa blends comfort, convenience, and island charm for your next Florida getaway.brbrHighlightsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 1 Queen, 1 Twin Daybed, 1 Twin Trundlebr• 5-minute walk to Siesta Beachbr• Private garden-view patio with seatingbr• Newly remodeled with modern finishesbr• Washer and Dryerbr• 1 covered parking spacebr• Shared pool and shuffleboardbr• Community BBQ grillsbrbrThis villa was thoughtfully renovated with an open floor plan and enlarged bathrooms, each featuring sleek walk-in showers. Step outside to your shaded private patio and relax on swivel rockers with ottomans. Perfect for unwinding after a day on the beach. Guests also enjoy access to Jamaica Royale’s sparkling pools, shuffleboard courts, and community grills for alfresco dining.brbrThe main living area is bright and inviting, with tropical decor and plenty of seating. A round dining table expands to seat up to eight guests, while the kitchen boasts stainless appliances, a dishwasher, and all the essentials for preparing meals at home. The spacious utility closet includes a washer and dryer for added convenience.brbrThe primary suite features a king bed, large closet, and ensuite bath with a walk-in shower. The guest bedroom is ideal for families, offering a queen bed plus a twin daybed with trundle that can convert into a king. Both bedrooms include wall-mounted drying racks for beach towels and swimsuits. A second bathroom with a walk-in shower is located in the hallway.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbr• Second Bedroom: Queen bed, twin daybed with twin trundle, hallway bathroom with walk-in showerbrbrSet within the desirable Jamaica Royale community, you’ll be steps from the office, grills, and lush garden areas. Siesta Key Beach, with its world-renowned quartz sand and turquoise Gulf waters, is only a short walk away, while Siesta Key Village’s shops and dining are just two miles from your door.brbrJamaica Royale 108 by Tropical Sands Accommodations is the perfect balance of relaxation and convenience on Siesta Key. Book your stay today and start making memories by the sea!

Jamaica Royale 108 Garden View!

Siesta Key, Florida, United States

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Bath

Sleeps

$313.53

Gulf Holiday Unit 7 by Tropical Sands Accommodations brMinimum stay duration 3 days/nights br brDiscover Gulf Holiday Unit 7, a one-bedroom, one-bathroom condo just a short 2-minute stroll from the award-winning Siesta Key Beach! This inviting retreat features a shared heated pool and a prime location near the shops, restaurants, and nightlife of Siesta Village, making it the perfect choice for couples or small families seeking an unforgettable coastal getaway. brbrHighlights: br• 2-minute walk to Siesta Key Beach br• 1 Bedroom / 1 Bathroom br• 1 Queen bed, 1 queen sleeper sofa br• Shared heated pool br• One block from Siesta Key Village dining and shopping options br• Beach chairs and cart provided br• Community laundry facility br• Recently refreshed interiors for a modern and inviting atmosphere br• 1 Parking space brbrUnwind at the shared heated pool, which provides the perfect place to relax and soak up the sun. When it’s time for sun and sand, you’ll appreciate the condo’s unbeatable location, just a short 2-minute stroll to the renowned Siesta Key Beach. Feel the soft white sand beneath your feet and take in the stunning turquoise waters as you enjoy a fun filled day at the beach. The provided beach chairs and beach cart make it effortless to transport your essentials, ensuring you can effortlessly enjoy a day of relaxation by the shore. This prime proximity to the beach allows for quick and easy access, making Gulf Holiday Unit 7 a fantastic choice for those looking to indulge in the vibrant beach lifestyle that Siesta Key has to offer. br brInside, the open concept layout seamlessly combines modern design with comfort. The living area includes a cozy sofa and accent chair for lounging, along with a queen sofa bed for additional sleeping arrangements. The bright kitchen is equipped with stainless steel appliances, generous cabinetry, and all the essentials you need to prepare delicious meals. A stylish dining table offers the perfect space for enjoying breakfast or evening dinners together. br brThe primary bedroom features a queen bed adorned with coastal inspired decor and soft linens, providing a restful retreat after a day of beach adventures. The bathroom boasts a walk-in shower with fresh, modern finishes. brbrRoom Details: br• Primary Bedroom: Queen bed br• Living Room: Queen sofa bed br brThis condo ensures you have all the comforts of home, including a community laundry facility for your convenience. br brWith its unbeatable location near Siesta Key Beach and Siesta Village, Gulf Holiday Unit 7 by Tropical Sands Accommodations offers modern comforts and shared resort style amenities, making it the ideal spot for a carefree island vacation. Reserve your dates today and get ready for your Siesta Key escape! br 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. brbr1 car maximum is able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Gulf Holiday unit 7!

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$217.59

Peppertree Paradise #507 by Tropical Sands Accommodations brMinimum stay duration 30 nights br brWelcome to Peppertree Paradise #507, a bright and stylish two-bedroom, two-bath condo located in the sought after Peppertree Bay community on beautiful Siesta Key. This charming home is infused with vibrant artwork, colorful accents, and coastal charm, offering both personality and comfort for your extended island getaway. With resort style amenities and private access to the world-famous white sands of Siesta Beach, it’s the perfect retreat for families or friends looking to relax and unwind. brbrHighlights: br• Private access to Siesta Key Beach br• 2 Bedrooms / 2 Bathrooms br• 1 King bed, 1 queen bed, 1 queen sleeper sofa br• Two heated swimming pools, clubhouse, fitness center, and tennis and pickleball courts br• BBQ area br• Vibrant interiors featuring coastal decor and modern finishes br• Screened lanai br• In-unit washer and dryer br• Beach cart provided br• 1 Covered parking space br brEnjoy full access to the fantastic amenities within the Peppertree Bay community, which includes two heated swimming pools, a fitness center, a clubhouse for social gatherings, and well maintained tennis and pickleball courts. Plus, with private access to Siesta Key Beach just steps away, you can easily indulge in sun, sand, and surf at this award-winning beach. br brThe condo’s design beautifully blends comfort with creativity, featuring colorful accent walls, playful artwork, and inviting seating that make each space feel unique. The open living area boasts plush furnishings alongside a smart TV and provides direct access to the screened lanai, an ideal spot for enjoying your morning coffee or evening cocktails. The dining area is perfectly set for memorable meals together, while the fully stocked kitchen includes stainless steel appliances, ample cookware, and generous prep space for at-home dining. brbrRoom details: br• Primary Bedroom: King bed with ensuite bathroom with a shower/tub combo br• Second Bedroom: Queen bed with ensuite bathroom with a walk-in shower br• Living Room: Queen sofa bedbr brLocated in the heart of Siesta Key, Peppertree Paradise #507 places you close to local dining, shopping, and the vibrant nightlife of Siesta Key Village. Spend your days lounging on the stunning Siesta Beach, kayaking in the bay, or exploring nearby Sarasota attractions, including theaters, galleries, and the famed Ringling Museum of Art. brbrMake Peppertree Paradise #507 your next home away from home and experience the best of Siesta Key living. Book your stay today with Tropical Sands Accommodations! br 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. brbr1 car maximum is able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Peppertree #507- Private Access

Siesta Key, Florida, United States

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Bath

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$428.44

Perfect for a family vacation or a romantic getaway. Gorgeous 2 bedroom, 2 bath condo at the luxurious Crystal Sands resort directly on Crescent Beach in Siesta Key. brbrThis 8th floor tower unit has just been beautifully remodeled to include all new furnishings, appliances, flooring, etc. Enjoy magnificent gulf views from every room. A spacious screened in lanai spans the width of the condo with access from the living room and both bedrooms. Just steps away from the powdery white sands of Siesta Key. brbrRelax on the private beach with loungers already set up for you. 2 heated swimming pools are provided for your enjoyment, one overlooking the beach. Free WiFi and cable are provided and TV's are in the living room & both bedrooms. Washer & dryer are in the unit so you can pack light.brbrCrystal Sands is just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more, or a short walk to nearby restaurants, convenience stores, and water sports rentals. Hop on the Free Siesta Breeze Trolley in front of the complex and explore what the island has to offer.brbrA 2 week minimum is required to rent at Crystal Sands.

Luxury On The Beach in the Heart of Siesta Key at Crystal Sands 809

Siesta Key, Florida, United States

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