Vacation Rentals By Owner In Siesta Key, FL

Beautiful Condo Directly Across from Siesta Key Beach at Our House At The Beach. Located on the 2nd floor facing the Gulf of Mexico. The building has an elevator in the secure lobby.brbrWatch the sunset from the wrap around balconies in this beautifully decorated two bedroom condo directly across from sun kissed Siesta Key Beach! Spacious and inviting with ceiling to floor sliders on two entire walls for incredible tropical views. The new kitchen including all new appliances, fixtures, counters & flooring was completed in December 2019, new flooring in living room and dining room installed in 2022. Plenty of chairs & loungers are provided on both balconies to relax, and there is also a table & chairs for dining outside.The condo features 2 bedrooms & bathrooms on opposite sides of the unit for added privacy. Sleeps 6 comfortably with a king bed in the master, 2 twins in the guest bedroom, and a queen sleeper sofa in the living room. A full size washer and dryer are provided in the unit so you can pack light. Free WiFi and cable are provided, and TV's are in the living room and both bedrooms.brbrOn site amenities include a heated Olympic size pool, tennis courts, outdoor gas grill, gazebo, and covered parking. The condo is within walking distance either by sidewalk or beach to shopping, dining and night life fun at Siesta Key Village. Hop on the free Siesta Key Breeze trolley in front of the complex and ride to Turtle Beach, Siesta Key Village, and all points in between.

Watch Sunsets from Our House At The Beach! 2nd Floor, Gulf Facing E101

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$492.53

Just completed renovation Sept 2024! Three separate sleeping spaces, Primary with a King bed, Guest Room with a Queen, and third room with two twins. All rooms have ceiling fans and Roku TV's. Plus two large bathrooms, both with dual sinks and separate shower/toilet rooms.brbrIt will be hard to find better views on Siesta Key. Enjoy the most colorful sunsets with expansive views right off private balcony. Updated, modern TOP FLOOR unit with expansive OCEAN views and Sarasota Bay, PLUS downtown Sarasota! Fully renovated with quartz countertops in kitchen and bathrooms, stainless steel appliances, new luxury vinyl floors and updated furnishings.brbrNeed to work, no problem- two desks provided PLUS a monitor, and super-fast wifi. Washer and Dryer in unit. Relax in the family room with two couches and chair that all have electronic reclining. Enjoy upgraded cable with Roku streaming on all 3 TVs and Sony soundbar and subwoofer in family room. Plenty of beach chairs, umbrella, toys, wagon, pickleball rackets provided- or rent chairs and umbrellas from the service right at Anchorage's private beach entrance. Very quiet unit on top floor with only one shared wall with another unit.brbrGated entry with one covered parking spot and ample open parking spaces. Heated Olympic Size swimming pool, lighted tennis/pickleball courts, shuffleboard, cornhole, basketball, gas grills and exercise room.brbrAmenities Include:brbr- In-Suite washer dryer: YESbrbr- TUB/SHOWER: Ybrbr- Balcony: 1brbr- BBQ Grill: 2 Gas Grillbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: KINGbrbr- Bed Size 3rd Rm: 2 TWINSbrbr- Elevator: 2brbr- Exercise Facility: YESbrbr- Floor No.: 10TH FLOORbrbr- Internet Access: YESbrbr- Walk in shower: Ybrbr- Parking: PRIVATEbrbr- Parking Space Type: # 27brbr- In suite washer dryer: Ybrbr- Electric Stove: Ybrbr- View: ISLAND/GULFbrbr- PICKLEBALL: Ybrbr- Island View: ISLANDbrbr- Tennis Courts: 3 TENNIS COURTSbrbr- Pool: YESbrbr

Anchorage PH-2

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$196.74

Newly updated 2 bedroom condo just a 5 minute walk to Crescent Beach in Siesta Key. The unit is located on the second floor. A short walk to coffee shops, restaurants, ice cream and boutiques. Heated pool in complex.

Seaside Condo in Siesta Key

Siesta Key, Florida, United States

Bed

Bath

5

Sleeps

$436.24

Jamaica Royale 803 by Tropical Sands Accommodations brbrWelcome to Jamaica Royale 803, a beautiful beachfront condo in the gated Jamaica Royale community on Siesta Beach. This bright two-bedroom, two-bath retreat offers stunning Gulf views from the private balcony and all the comforts of home for a 7-night minimum stay. Stroll along the private beach path to the island’s famous sugar-white sands, unwind by one of three heated pools, and hop on the free Siesta Key Breeze Trolley to explore local dining, shops, and entertainment in Siesta Key Village.brbrHighlights br• Beachfront building with private beach accessbr• Balcony with beach and Gulf views + outdoor diningbr• 2 bedrooms / 2 baths br• Beds: 1 king, 1 queen, 1 twin-over-twin bunkbr• 3 shared heated pools + shuffleboardbr• Washer and dryerbr• Shared BBQ grills and picnic areasbr• Elevatorbr• 1 assigned parking spacebrbrStep from your tower to a private stretch of Siesta Beach renowned for powdery white quartz sand and nightly sunsets. Between beach sessions, enjoy three sparkling heated pools, shuffleboard courts for friendly competition, outdoor showers, and shaded picnic spots with community grills for easy seaside cookouts. For even more island fun, a public pickleball court is just a short walk from the complex, perfect for a friendly match before heading back to the beach.brbrAn elevator lifts you to a bright, open living area with comfortable seating and a large TV, perfect for movie nights. Sliding doors frame turquoise water views and open to the furnished balcony for morning coffee and sunset dinners. The kitchen features stainless steel appliances, ample cookware, and a convenient island bar, while the adjacent dining table sets the scene for relaxed family meals.brbrThe primary bedroom is a peaceful retreat with a king bed, TV, closet storage, and balcony access to savor beach breezes. Its ensuite bathroom includes a walk-in shower and modern finishes. The guest bedroom suits kids or additional guests with a queen bed plus a twin-over-twin bunk, TV, and closet space. A hall bathroom with a shower-tub combo serves this room and the common areas.brbrMake your next Siesta Key getaway effortless at Jamaica Royale 803! A true beachfront retreat with Gulf views, resort amenities, and instant access to Siesta Beach and Siesta Key Village. Reserve your dates now with Tropical Sands Accommodations.

Discover Your Perfect Family Vacation at Jamaica Royale 803 in Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$139.03

Peppertree PerfectionbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbr*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.brbrThis second-floor condo offers privacy, seclusion, a view of the bay, and a host of other great amenities. You will enjoy access to two shared pools, a fitness center, and two lovely tennis courts on the community grounds. It even grants access to a private beach nearby!brbrWhat's nearby:brThis property is located directly on the Gulf of Mexico, with warm sugar sand and turquoise waters just a walk away. Nearby, you'll also find the famous Siesta Key beaches only a couple miles away, where a large pavilion, playground, and souvenir shop are also a part of the fun. The Siesta Key Village is only a short drive away. There you can enjoy dining and shopping while you take in the sights!brbrThings to know:brFree WiFibrFull KitchenbrThe HOA charges a mandatory registration fee of $100. The fee is charged as part of your reservation at the time of booking.brbrParking notes: There is free parking available for 2 vehicles.brbrDock details: brbrbrbrDamage 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.

Lovely Siesta Key condo with patio, pool & bay view - near beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$457.32

brbrIf you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably with a king, double and queen mattresses Just outside your door is Crescent Beach, consistently rated one of the top beaches in the world. Talk about convenient, just across the street are restaurants including Captain Curt's and it's award winning clam chowder, grocery, boutiques, and of course the Orange Octopus for that must have evening ice cream cone, all less than a 5 minute walk away. brbrThe condo has been remodeled and redecorated throughout. A new kitchen was added in the fall of 25’. Bathrooms were also updated Tastefully furnished in a 'beachy' theme, you will feel perfectly relaxed while letting you know you are on a great beach vacation. The living room seats 7 people comfortably with a new leather sofa & love seat and a recliner. There is a 50 smart TV with DVD player and sound bar that allows you to stream music from almost any portable devise including your phone. The living room is open to the dining room which seats 8, perfect for entertaining friends and family lending a light airy feeling throughout. A fully equipped new kitchen and appliances include a single serve Cuisinart coffee maker for that quick caffeine fix, ann anir fryer, slow cooker and a Ninja Professional Blender for a great smoothie anytime. A quick trip to Crescent Market (across the street) or Publix (less than a 10 minute drive away) to buy your essentials and you're set to enjoy. The master bedroom has a king size pillow top bed, flat screen TV, walk in closet and access to the private balcony. The master bath has a large tiled walk in shower and updated fixtures. The guest bedroom has both a queen and double bed with new mattresses, flat screen TV and walk in closet. The guest bathroom has a tiled tub/shower combination again with new fixtures. WiFi, cable television and ceiling fans throughout. brbrBut the real attraction is the beach. Crescent Beach is a fine white powdery sand that feels more like baby powder than sand. The sand stays cool even on the hottest summer day. The beach stretches for over three miles, great for walking, cycling and jogging. Crystal clear water with a very gradual descent makes the gulf very inviting for swimming, playing or just floating on a raft. Tropical breezes off the Gulf makes it comfortable even on the hottest summer day. A short walk down the beach, less than ten minutes, you will come to the Point of Rocks. A great place for snorkeling, diving, shelling and an occasional manatee sighting. Back at the Sea Shell there are plenty of lounge chairs that you can take right to the beach or sit under a shaded tiki hut or the large cabana. Relax in the gorgeous new tiki hut furnished with gas grills, picnic tables and a large bar area to sit and cozy up to while the pit master is grilling. There is also an open air grilling area overlooking the beach with again, picnic tables. There are four large outdoor grills, 2 gas and 2 charcoal available to use with prior reservations at the office. For the more adventuresome, parasailing, jet skis, boats, bicycles and more are available to rent all within walking distance. brbrJust an hour away from Tampa and Fort Myers and two hours away from Orlando Siesta Key is an ideal location for day trips. Sarasota itself offers many attractions including Mayakka River State Park, Jungle Gardens, Ringling Museum, Mote Marine Aquarium, St. Armand's Circle and more.brbrThe Sea Shell is a medium size complex with 49 units. Your private parking space is just steps from the elevator and stairs. No long walks from your car or waiting on elevators. The friendly and knowledgeable office staff is on premise and ready to answer any of your questions and give you great advice about the area.brbrWhether building sand castles with your children or grandchildren, taking long romantic walks, or sipping your favorite cocktail while watching an incredible sunset, our condo is the perfect vacation getaway. Just pack you suntan lotion and you'll be ready to enjoy your slice of paradise. We hope you stay with us and come back often.

Location,Location,Location-Beachfront-Your Slice of Paradise-#1 Beach in America

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$807.37

Holiday House - Steps to Siesta Beach, Pet Friendly, Walk to Siesta Key Villagebrbr Why You'll Love This HomebrHoliday House gives you that rare Siesta Key experience where the beach, the Village, and your own bright upstairs retreat all feel effortlessly connected. Spend your days wandering from soft white sand to cool indoor comfort, then back out to lively evenings just steps away. The home feels cheerful and easy, with space to gather, room to relax, and a breezy island atmosphere that makes every moment feel like vacation.brbr ‍ ‍ Perfect ForbrFamilies and small groups who want walkability, pet-friendly comfort, and a laid-back island atmosphere.brbr ️ Imagine ThisbrYou start your day with complimentary beach gear in hand and head to the beach, just steps away from your home. The breeze carries faint salt air, reminding you that Siesta's famous white sand is just moments away. Beach chairs and towels in hand, feeling that light vacation excitement as you walk toward the Gulf.brbrAs the sun dips low, you fire up the grill beneath the Tiki cabana and watch the sky glow with soft streaks of orange and coral. Every part of the day feels smooth and unhurried—like the island itself is reminding you to breathe, slow down, and savor the moment.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath with Walk-In Shower, TVbr• Bedroom 2: King Bed, Hall Bath, TVbr• Bedroom 3: Two Full Beds, Hall Bath, TVbr• Living Room: Queen Sleeper Sofa, TVbrbr Explore the Areabr• 300 Feet to Siesta Key's Sunset Beachbr• 0.1 Miles (2-Minute Walk) to Siesta Key Villagebr• 0.1 Miles to Local Dining, Coffee Shops and Boutiquesbr• Free Siesta Key Breeze Trolleybrbr⌛ Don't wait—This home is in the perfect location! Your reservation includes peace of mind with our CottageClean™ program, featuring a detailed 6-hour deep clean and a 35-point inspection before every arrival.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Your furry friend is welcome! This property is dog-friendly for dogs under 25 lbs with an additional pet fee. Breed restrictions apply. Please notify us in advance if you'll be bringing a pet. The home is part of a duplex and located on the second floor. It may share walls, floor/ceiling, or outdoor spaces. If any guest has difficulty with stairs, please contact us for alternative accommodations.

Private Vacation Home

Holiday House | Steps to Siesta Beach, Pet Friendly, Walk to Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$436.53

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Lulu's Key House Loggerhead! brbr brbrThe condo is only a couple of blocks away from famous Siesta Key beach access #5 and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. brbr brbrLOCATION HIGHLIGHTS: brbr- Just a couple of blocks to famous Siesta Key Beach access #5 brbr- Steps to restaurants, shops, coffee houses, and nightlife brbr- No car needed to enjoy the village and beach brbr- Heated communal pool on-site with loungers and umbrella, outdoor shower brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom 2nd floor unit, accessible by stairs (851 sq ft) brbr- Crown molding, solid stone counters, stainless kitchen appliances, plantation shutters, wide plank porcelain tiles, outdoor shower brbr- Two sets of shared washers/dryers in building at no cost brbr- Free WiFi and cable brbr- Access to open patio and swing brbr brbrLIVING ROOM: brbr- Large Smart TV with cable brbr- Open concept brbr- Sofa is a queen sofa sleeper for unexpected guests brbr brbrKITCHEN AND DINING: brbr- Modern kitchen with quartz countertops and tiled floors brbr- New stainless steel appliances including dishwasher and microwave brbr- Dining table seats 6 right off the kitchen brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: queen bed, with TV and closet space brbr- Master ensuite bathroom: walk-in shower with glass doors brbr- Guest bedroom: king bed with closet space, TV brbr- Guest bathroom: walk in shower with glass doors, vanity brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: beach cart, beach chairs, umbrella, and beach towels brbr- Exterior camera pointed to parking lot for security brbr brbrLOCAL FAVORITES: brbr- Steps to Siesta Key Village for shopping, dining, coffee, and nightlife brbr- Short walk to Siesta Key Beach and Gulf waters brbr brbrIMPORTANT INFO: brbr- Two assigned parking spots marked “Loggerhead” brbr- No smoking inside the unit or building brbr- No pets allowed brbr- Option to book all 4 units for full private group stay brbr- Confirm approval for special vehicles including boats, motorcycles, trailers, jet skis, kayaks, golf carts, or oversized/commercial vehicles brbr- Flexible dates of stay brbr brbrBOOK YOUR BEACH ESCAPE BEFORE DATES FILL UP!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.

LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Beach Gear Included!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$932.2

Experience one of the most exceptional penthouse residences in all of Siesta Key. Perfectly located in the heart of Siesta Key Village, this luxury condo is truly unmatched in location, size, privacy, and amenities.brbrEnjoy the exclusivity of a private elevator entrance, private garage, private rooftop terrace, and six exterior balconies, offering multiple spaces to relax, entertain, and soak in the coastal atmosphere.brbrThe main living area features a spacious open-concept design with ample seating, ideal for gathering with family and friends. The chef’s kitchen is fully equipped with top-of-the-line, state-of-the-art appliances and everything needed to prepare meals for the entire group. Adjacent to the living room, the dining area seats eight comfortably, complemented by additional bar seating at the kitchen island.brbrA second living space serves as a dedicated game and entertainment room, complete with a bar-style kitchenette, full-size refrigerator, microwave, ping-pong table, TV lounge, and a chess coffee table. This area opens to its own private balcony, making it an ideal retreat for teens or guests looking for a separate space to unwind.brbrSleeping accommodations are perfect for large families or groups, comfortably sleeping up to 10 guests:brbrTwo luxurious king master suites, each with a private ensuite bathroombrbrOne guest bedroom with a queen bedbrbrOne guest bedroom with a bunk bed featuring a queen on the bottom and a Double XL on topbrbrGuests also have access to a heated outdoor pool and spa, along with a private grill for enjoying BBQ meals with family and friends.brbrFor your beach days, Coastal Oasis includes complimentary beach equipment—chairs, umbrella, and beach buggy—for your convenience.brbrAdditional details:brbrSleeps up to 10 guestsbrbrNo pets allowedbrbrMinimum age requirement: 25 years old

Private Vacation Home

Luxury 4-bedroom Penthouse in Siesta Key- Private rooftop terrace

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$184.52

We have been to many beaches and keep coming back to this beautiful place time and time again. Our condominium is located in the Bay Oaks complex across from Crescent Beach on Midnight Pass. It is approximately 1 mile to drive to the public beach or a 15 minute walk. Beach connoisseurs have long hailed this beach as one of the best in the world. Its famous white sand beaches are perfect for long walks and beautiful sunsets. The beach has lifeguards on duty, volleyball nets and chair and umbrella rentals. The condominium is conveniently located within walking distance of many restaurants and a short car ride to shopping malls, movie theaters, casual and fine dining, churches, and over 50 golf courses.brbrThis fourth-floor condo offers privacy as well as a quiet lanai that overlooks the lush, tropical foliage and manicured landscape of Bay Oaks. The elevator (with luggage cart) is close-by and walks out to your individual covered parking space. You are also a very short distance to the tennis courts, heated pool, sauna, showers, recreation room with pool table and lounge where various social gatherings are scheduled. There are marinas nearby for boat rentals, sport fishing and parasailing rides.brbrThe master bedroom has a king-sized bed, two nightstands, dresser, TV and walk-in closet and adjoins a full bathroom equipped with shower and tub enclosure. The second bedroom has two single beds, nightstand, dressers and walk-through closet which leads to the second full bathroom complete with tub and shower enclosure. The living room has a leather couch, chair, end tables and TV/DVD entertainment center. The dining area has a large table that seats four people comfortably. The lanai is located just off the living room and is equipped with patio furniture. brbrThe kitchen is fully-equipped and includes dishwasher, stove, microwave, refrigerator, toaster oven, food pantry, dishes, cookware and utensils. The full-size washer and dryer are located right off the kitchen in an enclosed area.brbrPlease call now to make your reservation. NO SMOKING OR PETS. brbrKeywords: Condo

Absolutely Affordable at Bay Oaks in Siesta Key

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$506.69

Siesta Key Location.brPer HOA rules only Saturday to Saturday stay is allowed and no other departure or arrival date can be accommodated.brbrYour dreams of a luxurious vacation have suddenly become true when you stay in this 3 bedroom 2.5 bathroom vacation home in Siesta Key. This updated condo puts a spin on fun and relaxation. Just steps from the beaches of Siesta Key, you are sure to have the trip of a lifetime!brbrThe 3 bedrooms in this home are as cozy as staying in your very own bed. The master has a king bed with patio access and an ensuite bathroom. The first guest room has 2 full beds while the other boasts 1 queen bed. With so much space, everyone will have rest and relaxation for your days out in the warm Florida sun. No matter which room you choose, you can bet you’ll wake up feeling like royalty every morning. Each living space here is absolutely made for family time. The living room boasts a large wraparound couch and features a 50 Smart TV. This is the perfect place for a movie night! The living room transitions into a game room where you can play billiards all night long. Challenge your family members to some friendly competition while you hang out. The kitchen is large and spacious, opening itself up to the rest of the home. Granite countertops and updated cabinetry match the aesthetic of the home - charming, modern and overall luxurious. brbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity 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 street

Comfortable 3bd house Disney (AN877)

Siesta Key, Florida, United States

3

Bed

Bath

6

Sleeps

$339.04

Siesta Key Location.brJanuary - April: per HOA rules only Saturday to Saturday stay is allowed and no other departure or arrival date can be accommodated.brbrBask in the ambiance of a true home when you stay in this gorgeous 2 bedroom 2 bathroom vacation home in the heart of Siesta Key! Steps from the beach, you are sure to get your fill of the warm Florida waters. The amenities are endless and the sun is too when you stay here.brbrTo begin, the kitchen here is where family will gather to cook amazing meals and memories will be shared. The necessities of home come with you on vacation when staying here. The kitchen overlooks the living room which turns into an indoor/outdoor space once you open up the sliding glass doors. In the living room, you’ll find cozy couches and chairs all ready for you to relax on after a day in the town. A family game or movie night is a welcome addition to the living room too! Each bedroom here screams relaxation. The master bedroom has a king bed, patio access and an ensuite bathroom. The guest room is outlined with 2 queen beds.. Both rooms are exquisite places to stay for your trip here!brbrbrGuests staying at The Anchorage on Siesta Key have access to America’s #1 beach.brbrEasily accessible by one of two bridges connecting to the mainland of Sarasota, Siesta Key is an 8-mile long, crescent-shaped barrier island with four main areas – Siesta Beach, Crescent Beach, Turtle Beach, and Siesta Key Village.brbrbrREFUNDABLE DAMAGE DEPOSIT: $300 will be added to total as a refundable damage deposit. This amount will be refunded after the check out, if no damage to the property has been detected during your stay.brCommunity 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 street

Gorgeous 2bd villa close to Disney (AN876)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$332.81

Welcome to your perfect Siesta Key retreat—a beautifully designed lakefront condo located on the second floor in the sought-after Gulf & Bay Bayside community. Professionally managed by Gulf Coast Vacation Rentals, this spacious two-story residence blends comfort, convenience, and the charm of Old Florida with updated features throughout.brbrThe condo features two elegant primary bedrooms, each with a king-size bed, generous walk-in closets, and private en-suite bathrooms with walk-in showers. An additional sleeping space on the second floor offers a full-size bed, making this home ideal for families or small groups seeking both privacy and flexibility. Each bedroom is thoughtfully stocked with extra pillows, blankets, and linens to ensure a restful stay.brbrThe open-concept living space includes a welcoming living room with plush seating—perfect for relaxing after a day at the beach—and a separate office area, making this home just as suitable for remote work as it is for vacation. The screened-in lanai spans the length of the condo and offers tranquil lake views through floor-to-ceiling screened windows. It's the perfect setting to sip morning coffee or watch turtles and birds glide across the water.brbrThe fully equipped kitchen is a chef's delight, complete with brand-new cookware, small appliances, and an inviting dining area. Whether you're preparing a simple breakfast or a full family dinner, you'll find everything you need to feel right at home.brbrThis property gives you access to a full suite of community amenities designed to elevate your stay. Spend your days lounging by one of two heated pools, enjoying a match on the tennis or pickleball courts, working out in the well-equipped fitness center, or grilling out at one of the two BBQ stations. For those who enjoy outdoor leisure, there are charming picnic areas and a fishing dock for peaceful afternoons spent by the water.brbrGulf & Bay Bayside is a unique, gated community inspired by Old Key West architecture. Set across 25 acres of lush tropical landscaping, the community features cedar siding and distinctive angled roofs that add character and charm. With beach access just across the street, you can easily enjoy one of the top-rated beaches in the country without the hassle of driving. For your convenience, beach essentials like a cooler and wagon are included for guest use.brbrWhether you're looking to unwind in a peaceful lakefront setting, enjoy a beach vacation, or explore all that Siesta Key has to offer, this condo provides the perfect base for an unforgettable stay. Reach out today to reserve your dates and experience the coastal lifestyle at Gulf & Bay Bayside.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Stunning lakefront condo on Siesta Key with private beach access - GBB 1315

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$393.44

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrWelcome to paradise! This lovely and updated 2-bedroom, 2-bathroom villa features a private ensuite with a king bed and a guest room that features 2 twin beds. It is perfectly situated on the widest part of Crescent Beach, offering both privacy and comfort for your stay. Enjoy a beautifully updated, spacious living and dining area, a fully equipped kitchen, central A/C and heat, a screened lanai, and covered parking.brbrJust a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Villa

Island House Beach Resort V3

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$572.22

Welcome to the gorgeous 2BR 3Bath beachfront townhouse nestled in the tranquil complex on Siesta Key, FL. Escape the big-city crowds and enjoy the lovely ambiance from the patio while being just a few steps from the pristine sandy beach, swimming pool, local restaurants, shops, and attractions. br✔ 2 Comfortable Bedrooms + Sofa Bed (Sleeps 8) br✔ Open Design Living br✔ Full Kitchen br✔ Patio br✔ Smart TV br✔ High-Speed Wi-Fi br✔ Complex Amenities (Pool, Beach Access, BBQ, Sports, Parking)

Spacious ~ Private Beach~Shuffleboard~Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$398.35

Welcome to Siesta Beach House, where a private beach and heated pool await you. Kickback, relax, and immerse yourself in the tranquil surroundings as you enjoy your well-deserved vacation. Unwind by the pool, stroll along the pristine beach, and let the soothing sounds of the gulf wash away your worries. Your perfect getaway starts here at Siesta Beach House Stay comfortably in Siesta Key at this 2-bedroom townhome. The bedrooms feature 1 king bed, 1 queen bed, and 1 double bed, ensuring a delightful night's sleep for all guests. With amenities like WiFi, AC, and a hair dryer, your stay will be enjoyable and stress-free. The property also offers 2 bathrooms with a shower and other essentials. Escape to this tranquil retreat and create lasting memories with your loved ones. We'll be available to answer any questions while you stay at our place.

Private Vacation Home

Charming, newly renovated townhouse on beautiful Siesta Key beach.

Siesta Key, Florida, United States

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Sleeps

$399.06

Discover your ideal vacation escape on Siesta Key in this spacious three-bedroom, two-bathroom condo located in the serene Gulf and Bay Club Bayside community. Professionally managed by Gulf Coast Vacation Rentals, this fully furnished retreat offers everything you need for a stress-free getaway, including a washer/dryer and a private garage. With tasteful décor and ample space, it's perfect for families or small groups looking to relax in comfort.brbrStep outside and take a short stroll to the beach access, where you can sink your toes into Siesta Key's world-famous white sandy beaches and soak up the breathtaking Gulf of Mexico views. Spend your days basking in the sun, collecting seashells, or enjoying the gentle ocean breeze.brbrWhen you're ready to explore, the vibrant local dining, boutique shopping, and entertainment options of Siesta Key Village are just minutes away. For added convenience, the Gulf and Bay Club Bayside community features two heated pools, tennis courts, and lush tropical landscaping, making it an idyllic setting for your Florida getaway. Experience the charm and beauty of Siesta Key—your unforgettable vacation starts here.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Bayfront Siesta Key condo with amazing views - GBB 1391

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$344.63

Welcome to Gulf & Bay Club Bayside, Professionally managed by Gulf Coast Vacation Rentals, where luxury and comfort meet the stunning vistas of the bay to create an unparalleled living experience. Our resort-style community offers a wealth of amenities designed to enhance your coastal lifestyle, including two heated pools, well-maintained tennis courts, and lush, tropical landscapes that provide a serene and picturesque environment.brbrSituated with easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living. Imagine stepping onto the soft, white sand of the world-famous Siesta Key Beach, known for its expansive shoreline and tranquil waters. As a guest, you will receive beach tags granting you beach access, ensuring a more exclusive and peaceful beach experience. We also provide beach chairs, conveniently stored in the condo's one-car garage, so you can fully enjoy your time by the ocean.brbrOur condo offers more than just proximity to the beach. You'll find modern conveniences and thoughtful touches throughout your stay. The front office provides access to a printer and computer at no additional charge, making it easy to stay connected or handle any work-related tasks during your visit. Additionally, we offer complimentary shuttle rides to nearby restaurants and shopping destinations along the Key, allowing you to explore the vibrant local area with ease and convenience.brbrWithin the condo, you will discover a beautifully appointed living space designed for relaxation and enjoyment. The spacious layout includes three bedrooms and two bathrooms, providing ample space for you and your guests. The updated décor and modern furnishings create a welcoming and comfortable atmosphere, perfect for unwinding after a day of beach activities or exploring the local attractions.brbrThe fully equipped kitchen features everything you need to prepare delicious meals, and the open-concept living and dining areas are ideal for entertaining or simply enjoying a quiet evening in. Step out onto the private balcony and take in the breathtaking bay views, a perfect spot for morning coffee or an evening glass of wine.brbrAt Gulf & Bay Club Bayside, every detail is designed to provide you with a memorable and luxurious vacation experience. Whether you are lounging by the pool, playing a game of tennis, or strolling through the beautifully landscaped grounds, you'll find that our community offers the perfect blend of relaxation and recreation.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Beautiful Siesta Key condo with two heated pools, tennis, pickleball and beach access - GBB 1304

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$319.95

Welcome to your home away from home at our spacious two-bedroom, two-bath second-floor condo, Professionally managed by Gulf Coast Vacation Rentals, nestled in the picturesque Gulf and Bay Club Bayside. This Key West-style cluster building offers a serene residential feel, ensuring tranquility while being just a short walk from the powdery white quartz sand of the world-famous Siesta Key/Crescent Beach.brbrRecently introduced to our rental program, this condo has been lovingly maintained by its previous owners. With new carpeting and fresh décor, it provides a relaxing and inviting atmosphere, perfect for your vacation. The unit includes all the comforts of home, including a washer and dryer, a single-car garage, and a private driveway. For your beach outings, we provide chairs, an umbrella, a wagon, and beach towels, ensuring you have everything you need for fun in the sun. Dedicated Wi-Fi and a landline in the condo will keep you connected throughout your stay.brbrThe community offers an array of amenities just steps away. Enjoy a refreshing dip in one of the swimming pools, play a match on the tennis or pickleball courts, or try your hand at fishing from the dock. For those who like to stay active, the workout room is at your disposal. Additionally, community gas grills are available for BBQ gatherings, allowing you to enjoy outdoor dining amidst the beautifully maintained, lush landscaping that enhances your tropical vacation experience.brbrGulf and Bay Club Bayside is family-friendly and meticulously maintained, ensuring a pleasant and enjoyable stay for all guests. Whether you are lounging by the pool, exploring the beach, or enjoying the peaceful ambiance of the condo, you'll find everything you need for a perfect getaway.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Spacious 2BR 2nd floor Siesta Key condo - GBB 1274

Siesta Key, Florida, United States

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