Vacation Condo Rentals By Owner In Siesta Key, FL

Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort style gated community offering two heated swimming pools, tennis courts, fitness room, gas BBQ grills, and fishing dock. All this nestled among lush tropical landscape and lakes. brbrArrive by car and utilize the garage or driveway for parking. Taking the stairs up to the second floor of the townhome, you enter through the front door into the home. Right away you will notice the updated eat-in style kitchen equipped with stove, fridge, microwave, and dishwasher. The kitchen also offers a breakfast bar opening out to the main living area. The living area is spacious and furnished with comfortable lounge seating for family and guests enjoying the 55 flat screen smart TV with HD programming and streaming services available. Just off the living area is the screened balcony overlooking a serine water feature and lake. The patio is furnished with outdoor dining set with seating for 6. Back inside you will also find the master suite on the main living floor. The master bedroom is furnished with king-size bed and TV. The ensuite bathroom features a shower and dual sink vanity. brbrFollow the stairs from the living room up to the loft area along with two additional guest bedrooms which share a bathroom. The one guest bedroom is furnished with queen-size bedroom set and TV while the other is furnished with a double and a twin with twin trundle and TV. brbrMinimum Stay Requirements: 1 week minimum Saturday to Saturday.

Updated and clean, two heated pool, tennis, and beach access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$239.84

There's nothing more refreshing than knowing you get to spend time in sunny Siesta Key. When you have a trip on the calendar and can't wait to make the most of every moment, booking your stay in Beach Road-Tropea is a must! This 1-bed, 1-bath abode is ideal for welcoming up to 4 guests at a time. That means that whether you're in town on an independent adventure, traveling with a significant other or enjoying a small group getaway, Beach Road-Tropea promises to be a home away from home that pairs comfort with the quality and convenience you deserve.brbrEmbrace a Prime LocationbrbrMaximizing the fun in Siesta Key comes down to booking a stay that keeps you close to the heart of it all. Beach Road-Tropea does that flawlessly simply by offering guests a great destination to enjoy! This property is located right across the street from Siesta Key Beach. That means that when you want to spend time soaking up the sun, you never have to go far to do so. Just a mile down the road from the front door, guests can enjoy time exploring Siesta Key Village which is packed with options in the way of restaurants, shops, bars, and nightlife venues! Around the corner, visitors can hop on the Siesta Key Trolley which is a charming and no-cost way to access the many landmarks Siesta Key hosts.brbrInterior Amenities to Enjoy brbrSpace, fresh island style and a touch of luxury too are yours for the enjoying when you book a stay in Beach Road-Tropea. This abode enjoys a spacious open design complete with large windows and a collection of tasteful furnishings to be found throughout. The living room hosts a turquoise sofa topped with colorful throw pillows which is settled in front of a glass-topped coffee table and large flat-screen television. brbrThe living room opens up to the dining room where guests can easily gather around the table for 4 when it's time to enjoy a meal together. Looking for more seating options It's easily found at the extended breakfast bar that adorns the large kitchen in this home away from home. The inspired culinary spaces also feature stainless steel appliances, ample cabinetry, and a decorative tile backsplash in stone gray.brbrGetting a good night's rest is easy to do in this property thanks to the fact that the bedroom hosts a king bed topped with a Casper mattress. Additional guest 3 and 4 will also enjoy a good nights sleep on the queen-size Murphy bed with Casper mattress. A large walk-in closet offers plenty of storage for your travel belongings. The units bathroom offers a shower and vanity. Beach Road - Tropea includes access to an outdoor shower for rinsing off coming back from the beach as well as an in-unit washer and dryer. brbrBook TodaybrbrWhen your Siesta Key adventure is calling, Rent Siesta Key is here to help. Reach out today to learn more about booking a stay in Beach Road-Tropea the next time you're in town!brbrPARKING: There is only room for 1 vehicle for this unit.

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$253.31

When you're overdue for a refreshing vacation, a trip to Siesta Key is always a good idea. Making the experience even more exciting is the choice to book a stay in Midnight Cove II - Doveplum. This welcoming 3-bed, 2.5-bath condo can easily accommodate up to 6 guests at a time and provide proximity to area fun while also incorporating the comfort, style, and convenience every traveler deserves! Integrated into a complex that sits next to a lush lagoon, guests will find that whether they're visiting with family or friends, a stay here offers up the scenery and style that they crave. brbrInterior AmenitiesbrbrWhen two-story living is just your style, Midnight Cove II - Doveplum is sure to please. This home away from home is spacious and bright, offering up an open floor plan for guests to enjoy that's designed to include large windows throughout. These features both frame the view and allow natural light to flood the condo during the sunny Florida daytime hours. brbrThe living room in this rental features a plush wrap around leather sectional sofa and matching armchair. Both are settled around a sleek glass coffee table and in front of a large flat-screen television. Dark finishes sit in beautiful contrast to the fresh white color palette featured throughout the main level of the condo. Floor-to-ceiling windows in the living room provide plenty of light to enjoy as well as an unobstructed view over the lagoon.brbrThe living room opens to the dining area and kitchen where guests can serve up a home-style meal when they choose to. The kitchen features a convenient breakfast bar, modern appliances and cabinetry already stocked with cookware as an added convenience. When it's time to dine, guests can gather at the table for six with ease. brbrGetting a good night's sleep is a breeze in Midnight Cove II - Doveplum. Each bedroom in this property hosts a plush mattress topped with high-quality linens and comforters as well as a television.brbrExterior FeaturesbrbrWhile exploring your surroundings is sure to inspire, this property has plenty of outside fun to enjoy right on-site as well. Guests will love that this condo has its own boat dock as well as private beach access just across the street when you want to access Siesta Beach or Crescent Beach. Looking for even more in the way of fun Make the most of the resort's tennis courts, BBQ area, and outdoor heated pool. brbrBook TodaybrbrEnjoying your Siesta Key adventure is easy when you have property professionals on your side to get you settled into style. Reach out to Rent Siesta Key today to learn more about booking Midnight Cove II - Doveplum the next time you're in town!brbrMINIMUM STAY REQUIREMENTS: 1 week minimum stay required. High season requires a Saturday - Saturday reservation.

Spacious vacation rental condo with lagoon views, beach access, and pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$216.03

Sink your toes into Siesta Key's white sand beaches and swim in the crystal clear waters of the Gulf of Mexico during your stay at this 2-bedroom, 2-bathroom Sarasota vacation rental condo! This 1,435-square-foot condo is located on Crescent Beach and comfortably accommodates 6 guests for a memorable seaside getaway. Situated in the Gulf and Bay Club Condominiums, this beachfront condo features fabulous on-site amenities including a secluded beach, 3 heated pools, a hot tub, and more.brbr-- THE PROPERTY --brbrOutdoor Dining Area | Direct Beach Access | Free WiFibrbrBedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Living Room: Sleeper SofabrbrCONDO HIGHLIGHTS: Flat-screen cable TV, DVD player, dining table, en-suite bathroom, private screened patio brKITCHEN: Stove/oven, drip coffee maker, Keurig single-serve coffee maker, toaster oven, toaster, blender, dishware/flatware, refrigerator, dishwasher, breakfast tablebrGENERAL: Washer/dryer, linens/towels, complimentary toiletries, central air conditioning/heating, hair dryer, laundry detergent, iron/boardbrFAQ: Step-free accessbrPARKING: Designated parking (1 vehicle)brbr-- THE LOCATION --brbrSAND & SURF: Siesta Beach Access (on-site), Siesta Key Drum Circle (0.6 miles), Crescent Beach (0.9 miles), Sarasota Beach (1 mile), Point of Rocks (2 miles)brTEE TIME: Tournament Players Club (6 miles), Village Green Golf Club (7 miles), Stoneybrook Golf and Country Club (7 miles), Serenoa Golf Club (10 miles)brHIT THE TRAILS: Phillippi Estate Park (3 miles), Red Bug Slough Preserve (5 miles), Stoneybrook Nature Trail (6 miles), Marie Selby Botanical Gardens (6 miles)brAIRPORTS: Sarasota-Bradenton International Airport (11 miles), Tampa International Airport (72 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-in

Beachfront Sarasota Resort Condo: Siesta Key View!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$222.49

The Siesta Heron Suites & Villas enjoys a proximity that is close to the heart of everything that makes Siesta Key special, and our Sand Dollar unit is another ideal example. One bedroom, one bathroom, and a spacious and open living area allows up to four guests to live together in comfort and harmony. Spend your days exploring the beauty of Siesta Key and the mainland areas of nearby Sarasota and Bradenton, located just over the bridge, and spend your night in the welcoming rooms of Sand Dollar, enjoying a vacation that reflects the beauty of Florida in every way.brbrA paver walkway leads to a patio just outside the front door of Sand Dollar, and as with the other units on this property, a small table and chairs offer the perfect way to enjoy your morning tea or coffee. Once inside, the laidback vibe welcomes guests, providing a living area in the open concept floor plan anchored by a comfortable sofa placed opposite a flat screen television. brbrSeating at the breakfast bar in the bright and cheerful kitchen gives meal time an intimate feel that will draw honeymooners closer together, and modern appliances continue to help encourage the closeness as dinners are prepared shoulder to shoulder. A coffee maker allows guests to start every day well caffeinated, and because it is a Keurig, tea drinkers and cocoa drinkers can purchase their favorite beverages and start out the day on the right foot as well.brbrThe bedroom is a large space, offering up a romantic ambience and a neutral décor that encourages a deep sleep, while bright accent colors help along happy dreams. The king bed is cloud soft and a ceiling fan keeps the room cool as it circulates the air on a warm summer day.brbrThe bathroom of Sand Dollar is a quiet room, offering updated fixtures and a vanity that will hold all the lotions and potions that make your bride feel beautiful. Fluffy white towels feel soft against sunburned skin because our attention to detail means we understand the aches and pains associated with too much sun.brbrAnd finally, we come to the amenity section of our tour of Sand Dollar. The community offers a quiet magic that will enhance your Siesta Key vacation and includes a community swimming pool, barbecue grills, and a deck that overlooks Heron Lagoon. The beaches of Siesta Key are in close proximity with Turtle Beach being the closest at only a mile away and the shops and restaurants that make our Florida island special are all within a 10 minute drive. brbrOptional:brElectric vehicle charging station available, provided by ChargePoint.brbrSleeping arrangements for guests 3 and 4 are twin-size roll-a-way beds available upon request.

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$270.75

The last of our Siesta Heron escapes offers something extra the others don't and that is an extra bedroom. Key Lime, the fifth unit in this tranquil community is a 2-bedroom, 2-bathroom unit with room for 6 guests to cohabitate happily. Offering a private screened-in patio, it is a popular choice for travelers with slightly larger families.brbrA sofa provides a comfortable place to read and relax on a lazy vacation day and the small table and chairs on the screened-in patio of Key Lime is an ideal spot to enjoy morning coffee or a sunset dinner. Open the door and walk inside where an open concept floor plan harbors no secrets. The living area with its wood-like tile floor and comfortable leather sofa faces a large flat screen television.brbrThe dining area tucked away in the corner of Sand Dollar is where games will be played, meals will be devoured, and adventure planning sessions will be held under the light of the lamp hanging over the table. Reminders of the herons that make Heron Lagoon their home adorn the walls of this space in the form of bright and colorful paintings that realistically depict their peaceful natures and serene beauty.brbrGranite countertops, stainless steel appliances, and custom cabinets painted a crisp white give the kitchen a modern appeal, while the shabby chic backsplash softening the space and adding a beachside cottage feel. As in the other Siesta Heron units a Keurig coffee maker allows coffee, tea, or even cocoa drinkers to start out each day the way they love best. brbrKey Lime provides a beautiful master suite, offering a queen bed topped comforter. The bath is an updated room, featuring a wide granite topped single vanity and a walk in shower backed with tiles that resemble wood flooring.brbrBedroom number two is also furnished with a king sized bed for additional guests to utilize. Occupants can pull the blinds closed before drifting off to dreamland and sleep in as late as they want, but there is so much to do on Siesta Key we think getting up with the sun may be a good idea after all!brbrMinimizing the possibility of morning traffic jams when six people are staying under the roof of Key Lime, the second bath features a tub shower combo and another wide and spacious single vanity topped with granite. White cabinets and a dark framed mirror give the space a modern appeal.brbrIf even more sleeping is needed, there is an air mattress that can be setup for you in the living room for those additional house guests. brbrAs with all of our Siesta Heron units, it is the outside spaces that will thrill and delight. A community pool that is heated in the winter months, grills placed strategically throughout the property, and a large deck that looks over the tranquil waters of Heron Lagoon are just a few of the amenities you will find in this quiet community. Beach cruisers and beach gear make beach days that much more fun and a coin laundry, although not glamorous or exciting, can be a life saver when traveling with kids who can't help but make messes everywhere they go!brbrOptional:brbrElectric vehicle charging station available, provided by ChargePoint.

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$329.37

Nestled on the southernmost end of voted #1 Beach in America, The Pointe of Siesta Key is a true slice of paradise, surrounded by everything your heart desires.brbrStart your day with a refreshing workout at the gym, soak up the Florida sun by the pool, sizzle up a barbecue feast at the gazebo, or simply unwind with friends at the welcoming clubhouse.brbrFor those with a passion for angling, cast your line from the dock or explore the abundant fishing spots on the property. Here, every day feels like a waterfront adventure.brbrExperience Siesta Key living at its finest in this meticulously located condo, where the views stretch from sunrise to sunset, and the amenities are tailored for a life of leisure and enjoyment. This is more than just a rental; it's an invitation to embrace the coastal lifestyle and make lasting memories.

Welcome Sunrise to Sunset With Gulf to Bay views from Beautiful 2 Bedroom Condo

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$209.39

Summary:brbrSecond and third floor Bayfront townhome. Living area on second floor and interior stairs lead to bedrooms on third floor. Top of the line unit, offering travertine floors, new kitchen & baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet service. Screened & open balconies off the living room and master bedroom overlooking the bay and picnic area. Covered parking. King, Queen & sleeper, sleeps 6, 1 week minimum.

Bay Oaks B-22

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$294.63

Coastal Elegance with Unparalleled Ocean Views | Siesta Key brbr brbrExperience coastal luxury and breathtaking Gulf views from this serene 15th-floor retreat in an exclusive Siesta Key complex. This beautifully decorated condo offers private beach access and panoramic ocean views, creating the perfect setting for your Florida escape. brbr brbrHighlights brbr-15th-floor condo with sweeping Gulf of Mexico views brbr-Private balcony for sunrise and sunset viewing brbr-Private beach access to Siesta Key’s renowned quartz-crystal sands brbr-Elegant living area with floor-to-ceiling windows, comfortable seating, and flat-screen TV brbr-Fully equipped gourmet kitchen with modern appliances, granite countertops, and dining essentials brbr brbrBedrooms & Bathrooms brbrPrimary Suite brbr-King-size bed with premium linens brbr-En-suite bathroom brbrGuest Bedroom brbr-Queen-size bed brbr-Access to shared full bathroom brbr brbrAmenities brbr-Heated community pool brbr-Complimentary high-speed Wi-Fi throughout the condo brbr-On-site laundry facilities within the complex brbr-Secure parking for one vehicle brbr brbrImportant Information brbr-Non-smoking and pet-free property brbr-Application required prior to booking (please allow time for processing) brbr-Due to balcony design and high-floor location, not suitable for small children brbr brbrLocation brbr-Ideally situated just minutes from Siesta Key Village, where you can enjoy: brbr-Boutique shopping and local dining brbr-Beach bars and entertainment brbr-Kayaking, paddleboarding, and other water activities brbr brbrWhether you’re seeking a romantic getaway or a peaceful coastal retreat, this luxurious ocean-view condo provides the perfect backdrop for your Siesta Key vacation.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Expansive Gulf Views! Your Dream Rental | Private Beach | Pool | Steps to Siesta Key Village

Siesta Key, Florida, United States

1

Bed

Bath

4

Sleeps

$450.7

Gulf and Bay Club Unit B110 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit B110, a spacious three-bedroom, two-bath condo perfectly situated within one of Siesta Key’s most sought-after beachfront communities. Located just a short five-minute stroll from world-famous Siesta Beach, this inviting retreat blends resort-style living with all the comforts of home. Enjoy access to incredible community amenities, including heated swimming pools, a relaxing hot tub, tennis and pickleball courts, and a fitness center, all while being minutes from Siesta Key Village’s local restaurants, boutiques, and laid-back island nightlife.brbrHighlightsbr• 3 Bedrooms / 2 Bathroomsbr• 1 King, 2 Queens, 1 Twinbr• 28-night minimum staybr• Less than 5-minute walk to Siesta Beachbr• Access to shared heated pools and hot tubbr• Community tennis and pickleball courtsbr• Beach chairs providedbr• Washer and dryer in unitbr• Shared shuffleboard, cornhole, and fitness centerbr• Convenient location near Siesta Key VillagebrbrGuests of Gulf and Bay Club can unwind and enjoy Siesta Key’s relaxed coastal lifestyle with access to resort-style amenities. Spend your mornings soaking up the Florida sunshine by the heated community pools or taking a short walk to the beach’s soft white sands. Stay active with friendly matches on the tennis and pickleball courts or break a sweat in the fitness center before cooling off in the refreshing hot tub. The community also offers cornhole and shuffleboard courts, adding extra fun to your stay.brbrStep inside to a bright and inviting open layout designed for comfort and connection. The living area features plush seating and a large smart TV, perfect for cozy movie nights or catching up after a day on the beach. The fully equipped kitchen includes a refrigerator, oven, microwave, dishwasher, toaster, and drip coffeemaker, making meal prep simple and convenient. Gather around the dining table for family meals or plan tomorrow’s adventures with ease.brbrThe primary suite provides a restful retreat with a king bed, smart TV, spacious closet, and a private ensuite bathroom featuring dual vanities and a walk-in shower. The second bedroom offers two queen beds, ideal for families or friends, while the third bedroom is furnished with a comfortable twin bed. A shared hallway bathroom includes a shower and tub combination for added convenience.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbr• Second Bedroom: Two queen beds, shared hallway bath accessbr• Third Bedroom: Twin bed, shared hallway bath accessbrbrThis condo also includes a washer and dryer, complimentary Wi-Fi, and provided beach chairs for your convenience. One designated parking space is available for guest use.brbrWhether you’re planning an extended stay or a month-long escape to paradise, Gulf and Bay Club Unit B110 by Tropical Sands Accommodations offers everything you need for a relaxing Siesta Key getaway. Enjoy the community’s endless amenities, stroll to the beach, and explore Siesta Key Village just minutes away. Book your next coastal retreat today and experience the laid-back beauty of Florida’s Gulf Coast!

Gulf and Bay Club-B110- Just 5 minutes from Siesta Beaches!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$405.6

Siesta Beach is TripAdvisor's No. 1 U.S. beach for 2026!brbrSiesta Key Beach Retreat • 2BR (3 bed, 2 1/2 bathroom) Duplex Condo • Heated PoolbrbrWelcome to your perfect Siesta Key island escape—a bright and comfortable 2-bedroom, 3-bed duplex condo located inside the beautiful Bay Oaks community, one of the most peaceful and scenic spots on the island. Surrounded by mature oak trees, tropical landscaping, and waterfront views, this relaxing retreat offers the perfect balance of resort amenities, quiet island living and beach proximity (the public beach access points are a short walk down the street). brbrWhether you're planning a family beach vacation, couples getaway, or relaxing winter retreat, this condo gives you everything you need to experience the laid-back charm that makes Siesta Key one of the most loved beach destinations in the United States.brbrComfortable Coastal LivingbrInside the condo you’ll find a bright and welcoming coastal space designed for comfort after long days in the sun.brThe open living area features comfortable seating, a 55 smart TV for streaming your favorite shows, and plenty of natural light and pool view lanai. The space flows into a fully equipped kitchen and dining area, making it easy to gather for meals, games, or planning your next beach adventure.brThe condo comfortably sleeps up to six guests with a practical layout perfect for families or small groups.brSleeping arrangements include:br• Primary bedroom with a comfortable King Size bedbr• Second bedroom with 2 full-sized bedsbr• Spacious living area for relaxing after beach daysbrBoth bedrooms have bathrooms/showers inside of the room.brWith three total beds, everyone has space to unwind and recharge for the next day’s island adventures.brThis is a 2nd floor unit (with both bedrooms on the 3rd floor) so you'll need to walk up a flight of 15 steps to reach the front door of the unit.brbrResort-Style AmenitiesbrGuests enjoy access to the Bay Oaks community amenities, which offer a true resort-style experience in a quiet tropical setting.brAmenities include:br• Heated resort-style swimming poolbr• Private bayfront fishing pier perfect for sunrise views and dolphin sightingsbr• Tennis and pickleball courtsbr• BBQ and picnic areasbr• Clubhouse with billiards and lounge spacebr• Beautiful walking paths shaded by large oak treesbrThe bayfront pier is one of the hidden gems of the property—many guests start their mornings here watching dolphins, manatees, and boats glide along the Intracoastal Waterway.brbrMinutes to the BeachbrOne of the best parts of this location is how easy it is to enjoy the beach.brYou’re just a short, 5 minute walk or bike ride to Crescent Beach, famous for its calm turquoise water and soft white quartz sand. Siesta Key Beach—often ranked among the best beaches in the world—is also only minutes away.brEven better, the free Siesta Key trolley stops right outside the community, giving you easy access to:br• Siesta Key Beachbr• Siesta Key Village restaurants and nightlifebr• Local shops and boutiquesbr• Waterfront dining spotsbrYou can explore the entire island without needing to drive.brbrThe Perfect Island LocationbrBay Oaks is loved by visitors because it offers peaceful tropical surroundings while still being close to everything.brWithin minutes you’ll find:br• Beachfront restaurants and tiki barsbr• Fresh seafood diningbr• Kayak and paddleboard rentalsbr• Sunset cruises and dolphin toursbr• Snorkeling at Point of Rocksbr• Shopping and nightlife in Siesta Key VillagebrAfter a full day of island adventures, return to your quiet retreat to relax by the pool or enjoy a peaceful evening under the palms.brbrWhy Guests Love Staying HerebrGuests consistently love this condo for its:br• Relaxing tropical atmospherebr• Spacious 2-bedroom layout with 3 bedsbr• Heated resort poolbr• Beautiful bayfront fishing pierbr• Walkable beach accessbr• Free island trolley conveniencebrWhether you're here to soak up the sun, explore the island, or simply relax in a tropical setting, this Siesta Key duplex condo offers the perfect home base for an unforgettable vacation.brbrBefore booking, PLEASE ask me ANYTHING! I'm happy to address any questions and provide you a full list of my favorite things to do in and around Siesta Key so you can start planning your vacation immediately.

Siesta Key Beach Condo • 2BR, 3 bed, 2 1/2 bathroom, Duplex Condo • Heated Pool

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$508.5

This two bedroom/two bath condo is clean and waiting for your arrival! Centrally located on Midnight Pass in the gated community of the Sarasota Surf and Racquet Club, this unit has everything at your fingertips for the perfect vacation. Resort accommodations include two heated pools (one bordering the white Siesta Key sand), fitness center, private beach, business center, 24-hr security and office staff onsite to help with check-in and answer any questions you may have during your stay. You can walk the beach while watching the sunrise, or head one mile into the the famously known Siesta Key Village. The Resort provides lounge chairs at the pool and at the beach. Umbrellas are available to rent for a small fee. Beach front grills are available to reserve on a first come first serve basis.brbrThis fifth floor unit that has an amazing view of Siesta Key Beach. There is an elevator in the building. For your convenience laundry facilities are available on the 5th floor.br

2 BR/2 BA Beachfront Condo on Siesta Key

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$598.91

Siesta Key gulf side rental on one of the widest and most beautiful stretches of beach in the world. See why siesta key's beach has been rated #1 in the USA! There is a one month minimum rental for this property. You could be one of the first to stay here after a gut renovation down to the studs. This 1800 square foot, 2 bedroom 3.5 bath condo has a beachside pool that is unique on siesta key! And right next to this 1800 square foot unit separated by a carport is a 550 Square foot newly renovated condo that makes a perfect mother-in-law, nanny, or additional family suite. Enjoy each other's company during the day, but be able to relax and wind down in your own separate space at night. brEverything is brand new with ocean views from the second level of this two level condo. Very open floor plan with two bedrooms and a pull out sofa. Please call or e-mail with questions. Must see to appreciate these one-of-a-kind properties on Siesta Key. Two 60 HD tvs as well as a 30 in the bedroom. All new furniture, chefs kitchen, 4.5 baths, W/D in unit. Sleeps up to 10 between the two units. No pets no smoking. This is truly a one of a kind property with nothing like it on Siesta Key! Inquire today!!brbrPAYMENT SCHEDULEbrbrRefundable security deposit of $500.00 due within 14 days from the date you receive the contract plus $300 for each rental month.brbrBalance of total rent is due 90 days prior to arrival.brbrRates are discounted 5% for the third or more consecutive monthsbrbrStay must be continued occupancy in the same villa.brbrCANCELLATIONbrbrIf cancellation is 90 days or more prior to the rental start date, all monies will be refunded less $50.00 clerical fee.brbrIf cancellation is less than 90 days of rental start date, no refund of monies collected shall be made.brbrNo refunds for early departures.brbrSecurity deposit ($500.00) will be refunded in full for all cancellations. Any changes to the initial contract will be a charge of $50 per changebrbrOccupancy Rates quoted are for:brbrfour (4) people for a two (2) bedroom villabrbrMaximum Occupancybrbr2 bedroom villa - 6 peoplebrbrMust be 26 years of age to rent a villabrbrRecycling Guidelines and Rules & Regulations will be available in each villa. Cleaning fee included in rent.brbrNO PETSbrbrNO SMOKING IN VILLAbrbrTop 10 Beaches in the World 2017 Traveller's Choice Awards! Siesta Key #1 and only beach in the United States recognized!brbr1. Baia do Sancho, Fernando de Noronha, Brazilbrbr2. Grace Bay, Providenciales, Turks and Caicosbrbr3. Eagle Beach, Palm - Eagle Beach, Aruba, Caribbeanbrbr4. Playa Paraiso, Cayo Largo, Cubabrbr5. Siesta Beach, Siesta Key, Florida, United Statesbrbr6. La Concha Beach, San Sebastian - Donostia, Spainbrbr7. Playa Norte, Isla Mujeres, Mexicobrbr8. Radhanagar Beach, Havelock Island, Indiabrbr9. Elafonissi Beach, Elafonissi, Greecebrbr10. Galapagos Beach at Tortuga Bay, Puerto Ayora, Galápagos Islands

2 units next to each other on the #1 Beach in USA. Perfect vacation in Paradise

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$409.31

The Bayside UnitbrSecond floor bayside Siesta Key vacation rental with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now!brbrWhat Guests Lovebr∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moorsbr∙ The Balcony – royal palm views from balcony connecting bedrooms and living areabr∙ The Grounds – fishing causeway, private bay and Siesta Key beach access, lined by royal palmsbr∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sandsbr∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainmentbr∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balconybr∙ Activities – scooter, golf cart, bike and kayak rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – perfect fit for all with resort amenities and trolley to all top attractionsbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbr brbrThe BeachbrOur beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.brbrThe LocationbrWith so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.brbrBedroom DetailsbrThis is a 2nd-floor unit with an elevator. This two-bedroom unit has a king bedroom, a queen bedroom with additional full sized trundle, and a sleep sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrImportant Resort Limitsbr1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional emergency parking space is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.brbrHousehold Items ProvidedbrThis vacation rental comes with bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannotpurchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.

Gertrude's Siesta | Palm View Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$702.74

Beautifully updated from head to toe! Do not miss out on this top tiered 3 bedroom unit! Tile throughout with brand new furniture in all rooms. Top of the line appliances make this a chef's dream. You will have a washer and dryer in the guest bedroom closet. With 3 bedrooms and king beds in each room, this is perfect for a family or a couples retreat. Eat your breakfast with a view of America's #1 beach!

Beautifully Updated Gulf View, 2 Bed, 2 Bath with Loft, Sleeping 6

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$268.15

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Siesta Bayside Fountain View! brbr brbrThis is the perfect condo for your next beach getaway. Located across the street from Siesta Key beach through a private access point, this is a two bedroom condo with a screened in lanai overlooking a pond and banyan tree. With porcelain tile floors and bright & cheerful furnishings, you are sure to have an amazing time on Siesta Key. brbr brbrLOCATION HIGHLIGHTS: brbr- Just a 5-minute drive to Siesta Key Village with dining, shopping, and nightlife brbr- Nearby intracoastal bay access for fishing and boating brbr- Free shuttle service available to explore the area without driving brbr- Private beach access across the road brbr- Two heated community pools, Tennis courts brbr- Down the street from public beach brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 1 bathroom ground floor condo (959 sq ft) brbr- Screened lanai pond view brbr- Keyless entry and self check in brbr- Dedicated WIFI and cable brbr- Central A/C brbr- Parking in the driveway brbr- Private washer and dryer brbr brbrLIVING ROOM: brbr- Comfy couch with access to the screened lanai brbr- Big TV with cable brbr- Open concept brbr brbrKTICHEN AND DINING: brbr- Fully equipped kitchen with pots, pans, dishes, and small appliances brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed and TV with Xfinity cable brbr- Guest bedroom: full bed with sliders brbr- Bathroom: large separate vanity room, tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- South end: - Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery brbr- Village: Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog, Siesta Market, Beach Club, Big Tiki Lounge brbr brbrIMPORTANT INFO: brbr- Other than the beach access, no gulf side amenities (including their pool) are not available brbr- Garage is accessed weekly by staff to remove garbage brbr- Parking restrictions: no boats, motorcycle, trailers, jet skis, oversized or commercial vehicles allowed. brbr- Golf carts are allowed but must be stored in the garage or driveway brbr- Parking passes and onsite check in required brbr- AC maintenance is scheduled for Dec 2 between 8am -12 pm brbr brbrCOME MAKE LASTING MEMORIES IN THIS LITTLE SLICE OF PARADISE!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.brbrThis property does not allow Emotional Support Animals in addition to their no pet policy.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.brbrParking passes: 1 parking pass is provided. There is a fee for extra parking passes.

Resort Style Condo | Pretty Pond Views | Walk to Siesta Key Beach | Pool | Tennis!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$288.37

Your tropical paradise awaits you in this beautiful 2-bedroom 2-bathroom home located in beautiful Siesta Key. Just a short walk from the beach, this home is the beach paradise that you've been dreaming of. Warm wood accents and tropical decor make you feel as though you've stepped into a one-of-a-kind utopia.brbrAs you enter the home, the kitchen is the first thing you see with all of the necessities and upgraded cabinetry. As you cook here, you'll soon realize that having a full kitchen during vacation is very handy. Holiday meals or birthday celebrations are a breeze for this kitchen. The kitchen overlooks the living room which is the perfect spot to binge watch your favorite TV shows on large flat screen tv. Spend all night on the cozy couch catching up on all your guilty pleasures. Each bedroom here is fit for a king with flat screen tv's and ceiling fans! The large master bedroom has a king bed along with a newly remodeled walk-in shower ensuite bathroom, walk in closet and access to balcony. The newly decorated guestroom is outfitted with 2 queen beds, walk in closet and private access to balcony, reminiscent of the most luxurious hotel rooms. The guest bathroom is located right next to bedroom. New Hurricane tinted windows and sliding doors are in every room reducing sun glare and outside noise.brbrWhile you spend your time inside, you must make sure to take time and explore the gorgeous property! You can decide to swim at the pool, play a game of tennis, pickleball, or have a picnic or barbecue overlooking the intracoastal waters. We also have closet full of beach items, cooler, chairs, umbrella, noodles, beach cart, etc. Whatever you choose to do, it is sure to be a memory!brbrBook your stay today and experience it all for yourself!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: 2 QUEENSbrbr- Beds Pull-out: Queen Pull-outbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: 4th Floorbrbr- Internet Access: 7504 -6495719382brbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: 21/61brbr- Electric Stove: Yesbrbr- View: CANALbrbr- PICKLEBALL: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 405

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$288.37

brbrWe invite you to stay in our spacious condo managed by The Anchorage Community Rental Program. The Community Rental Program provides quality homes at a fair price and is managed by experienced professionals located onsite at The Anchorage complex. brbr'Siesta Chillin' is a spacious 2 bed 2 bath condo located across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation ...spot at The Anchorage Yacht and Tennis Club.brbrWhen you walk through the front door, a large welcoming space greets you with our freshly renovated open-concept kitchen, quality furnishings, new floors and luxury linens. Siesta Chillin is a very large unit at 1280 square feet. Everyone loves the spacious balcony that covers the entire width of the condo so it is accessible from the living room and both bedrooms. Southern exposure makes the condo bright and cheerful with picturesque views through the sliding glass doors in every room. The condo cpmplex backs up to the Inter-Costal Waterway with a serene park-like setting. Amenities include heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise roomnand free boat docking.brbrEverything you need is within walking distance from The Anchorage. The market, charter boats, fishing equipment, jet ski rentals, kayak/paddleboard rentals, para-sailing and bike rentals are just across the street. Convenience stores and several great dining establishments are only a short stroll to the hidden treasure of Siesta South Village. There is even some of Sarasota's best Karaoke! You can also hitch a free ride (tips appreciated) to Siesta Key Village where a wide range of shopping and dining fun awaits. Or, hop in you car and explore the local attractions of Sarasota and St. Armand's Circle.brbrSiesta Key is truly a little slice of heaven for everyone in the family from grandparents to the young children. Siesta Chillin is the perfect location for an amazing Siesta Key experience - whether you are staying for months to escape the northern winters or taking a short getaway to relax and rejuvenate. Come and chill with us in 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: 2 QUEENSbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: TILE KIT, CARPETbrbr- Internet Access: Yesbrbr- Parking: Yesbrbr- Parking Space Type: OPEN SPOTbrbr- Electric Stove: Yesbrbr- View: CANAL VIEWbrbr- PICKLEBALL: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 305 - Siesta Chillin

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$326.73

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 exposurebathes 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: 2 DOUBLESbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: 5th Floorbrbr- Internet Access: WIFIbrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: 92brbr- Electric Stove: Yesbrbr- View: Gulfbrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Gulf View: Corner Gulfbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 504

Siesta Key, Florida, United States

Bed