Vacation Home Rentals By Owner In Siesta Key, FL

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C, ample closet and storage space, cable TV, free calls to the USA, Canada and Puerto Rico. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts. PLEASE NOTE THIS UNIT DOES NOT HAVE GARAGE PARKING. FREE PARKING IS OUTSIDE.

Our House at the Beach C-217 A MUST SEE!!!!!!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$401.93

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the lake. The master bedroom suite also opens onto a balcony and has a newly renovated, en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom, also newly renovated. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

Our House at the Beach C-214 Quiet Location, newly updated

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$316.48

Second Floor Townhouse, steps to access unit, no elevator. brbrThis luxurious Lake House townhome directly adjacent to America's famed #1 beach - Siesta Beach, offers a spacious bi-level layout that includes separate dining and living rooms with Brazilian cherry hardwood floors. The eat-in kitchen is fully stocked with pots, pans, dishes, and flatware and a suite of stainless steel appliances including a dishwasher, glass top range, refrigerator and built-in microwave. The laundry includes a full-size washer and dryer for your convenience. The large living room features theater-style seating with twin power recliners, a queen-size sofa bed and access to the lighted balcony for dining, reading or sunning overlooking the lake. The master bedroom suite also opens onto the balcony and has an en-suite bathroom with walk-in shower, closet and dressing area. The second bedroom has an adjacent full second bathroom. The unit offers central A/C, ample closet and storage space, and a large flat screen HD TV Direct TV and streaming access. Garage parking for one car is included. Special amenities in this unit include soundproof bedroom windows, free wireless internet, free calls to anywhere in the U.S. and Canada and his and her road bikes. The development includes a private pool, covered pavilion area with gas BBQ, a picnic area and twin tennis courts.

Our House at the Beach C-220 Perfect Getaway!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$365.01

Welcome to Midnight Cove II 420D! Experience the best of Siesta Key in our spectacular 3-bedroom, 2.5-bathroom condo, perfect for families or friends seeking a relaxing getaway. Nestled within a serene, beautifully landscaped 14-acre property, this clean and fresh unit offers a lovely view of the canal waterway. With private beach access just a short stroll away, you can enjoy the world-renowned Siesta Beach, famous for its sugar-fine white quartz sand.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrDiscover the vibrant local community, rich with shopping, dining, and culture. The free Siesta Key Breeze Trolley makes exploring the area easy, eliminating the hassle of parking. Enjoy fantastic on-site amenities, including a heated swimming pool, tennis courts (with pickleball), a basketball court, clubhouse, and BBQ grilling area, along with an observation deck and private docks available for rent.brbrLocated just minutes from downtown Sarasota and its attractions, including the Ringling Museum of Art, Midnight Cove II is the ideal base for your adventure. brbrBook your stay today and embrace the sun-soaked paradise of Siesta Key at Midnight Cove II 420D! Your unforgettable beach getaway awaits!

Midnight Cove II 420D - Stunning Siesta Key Condo with Lanai

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1512.33

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked #1 in the U.S. #4 globally and is one of the best travel destinations in 2025. Siesta Key, a barrier island off the coast of Sarasota, in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village views and merely feet from both, we are confident that this vacation rental is one of the best in all of Siesta Key.brbrSiesta Key Dream’s largest and most luxurious vacation rental, features four levels, totaling 6-bedrooms, 9-beds, 6 full-bathrooms, & 2 half-bathrooms. Notable attributes include: a heated-pool, hot tub, 2-balconies, a roof-top sundeck, parking, a backyard and an elevator. With a premier location, beach access point #4 is 400 feet away, and the Siesta Key Village is one block away. In addition to a highly desired location, the unique property design allows beach and Gulf of Mexico views from multiple levels.brbrThis rental is perfect for family and friend gatherings and can accommodate up to 16 guests (14-adults & 2-children max). With 4 levels, an elevator between levels 1 to 3, each level has unique amenities as described below:br brLevel-1: Private heated pool, hot tub, two HDTVs, a gas grill, Traeger smoker, ping-pong table, putting green, privacy shrubbery, a refrigerator/freezer, and parking for 5 vehicles.brLevel-2: Four bedrooms with full bathrooms attached to each, three of the bedrooms have king size beds and direct walk-out balcony access, the fourth bedroom has 4 bunk-beds with a HDTV in each bunk. There is a wet bar with a sink, dishwasher and a beverage fridge. HDTVs are in every bedroom, plus the living room. An attached balcony with beach views looks over the private backyard, and the common area has a half bathroom.brLevel-3: 10-person dining table, 6-person island are inside, and a 6-person dining table is on the balcony. The kitchen has premium appliances that include a wolf range, fridge/freezer, ice-maker, dishwasher, microwave, Keurig and a drip coffee maker. The living room has a large window with views of the beach and ocean. HDTVs are in the living room and both bedrooms. The two bedrooms have attached full-bathrooms, king beds, and walk-out access to the balcony that present views of the beach, Gulf of Mexico, and the Siesta Key Village. There is also a half-bath attached to the kitchen area.brLevel-4: A spiral staircase from the 3-level balcony to the roof presents a sun-deck. The sun-deck has views of the beach, Gulf of Mexico, and the Siesta Key Village. Yoga equipment, sun loungers, a spotting telescope will give guests a one of a kind experience.brbrSiesta Key Dreams is happy to provide free-high-speed internet via WiFi, and DirecTV Stream’s premium channel package which includes live-sports, movies, DVR, and an extensive channel list. We provide a beach-load-out, that includes: beach chairs, beach umbrella, beach blanket, a cart, cooler, and beach towels.brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach (400ft) and the Siesta Key Village (400 ft). A 2-minute walk to the Siesta Key Village which has fine dining, cafes, ice-cream, bars, shops, a market, and everything in between.brbrIf you’re looking to soak up the sun and clear waters, a 2-minute walk to Sarasota Beach via beach access point #4 allows you to go back and forth to the beach with ease. In addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. brbrWe recognize that parking can be difficult to locate, which is why our rentals come with FIVE private, reserved spaces at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8AM - 10PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives in the Siesta Key area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrIncluded within your reservation are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods. To prepare for the numerous beach trips, we provide you with beach towels, beach chairs, beach umbrellas, beach blankets, coolers and carts to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors all on site! brbrShortly after you secure your vacation rental, you will receive a link where you can book local experiences provided by vendors throughout the island. For an additional charge, Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes.brbrSiesta Key Dreams also offers baggage drop-off prior to your check-in time.brbrLeading up to the check-in date, guests are supported via email & SMS.brbrBefore you check-in, just after you book the reservation, we send a link that allows you to acknowledge the House Rules/Rental Agreement, a request for your ID, photo and information for the guest verification process. This allows us to provide a safe location for our guests, neighbors, and employees.brbrPayments: 50% at the time of the booking & 50% within 7 days of check-inbrCheck Out: 10AM Check In: 3pmbrQuiet Hours: 12pm - 7AM brNo smokingbrLarge Gatherings (defined as 1.5x Guest Occupancy): Require approval from Siesta Key DreamsbrPets: No pets allowedbrParking: 5 vehiclesbrAdditional Details: After booking, see the Vacation Rental Agreement for all details

400ft to Beach, Ocean View, Pool, Rooftop, in the Siesta Key Village, 6-bdr

Siesta Key, Florida, United States

Bed

7

Bath

16

Sleeps

$364.66

Experience the vibrant setting of this 2BR 2.5Bath home, ideally situated on the private street with gated beach access. Take in the area's scenic beauty, explore the nearby Siesta Key Village, and discover a vast selection of beach activities and attractions. After a day of exploring, return to our home for a rejuvenating stay.brbr✔ 2 Relaxing Bedroomsbr✔ Cozy Living Areabr✔ Full Kitchenbr✔ Patiobr✔ Smart TVsbr✔ High-Speed Wi-Fibr✔ Community Amenities (Pool, Beach Access, Parking)brbrSee more below!brbrThe spacebrbrThis stylish townhouse, nestled just a few steps from Siesta Key Beach, is the perfect sanctuary for an unforgettable visit to Florida's West Coast. The open-concept living area is where you'll spend most of your time creating lasting memories with your loved ones. Unwind in the vibrant living room or watch a movie while the chefs prepare delicious homemade meals in the fully-equipped kitchen.brbrAfter a full day of exploring and beach hopping, you'll want to rest and rejuvenate for the next day's adventure. We've prepared two comfortable bedrooms to rest and recharge, providing all the comfort you need to continue writing your Florida fairy tale.brbrBut you don't have to leave the comfort of your home to feel the neighborhood's pulse or catch a breath of fresh air. The living room opens to a private patio, a dreamy setting perfect for an early morning coffee or an evening glass of wine.brbrWhether your goal is to explore the picturesque area, spend whole days at the nearby beach, or escape the everyday hustle and bustle, you'll find enough comforts and conveniences in this townhouse to make you never want to leave.brbr★ LIVING ROOM ★brImmerse yourself in the relaxing style and comfort of the living room, where you can watch the latest episode of your favorite TV show, take a break from beach adventures, and more while enjoying the modern living area.brbr✔ Snug Sofa with Pillows (can be converted into an extra Double Bed)br✔ Smart TV with Rokubr✔ Board Gamesbr✔ Lovely Sofa Chairsbr✔ Coffee Tables & Reading Lampsbr✔ High Table with Seating for 3br✔ Access to the Patiobrbr★ KITCHEN & DINING ★brThe living area continues with a fully-equipped kitchen and dining area, perfect for preparing and enjoying meals with your loved ones. The kitchen boasts an upscale contemporary design with spacious countertops and modern amenities, providing everything you need to create delicious dishes. brbr✔ Microwavebr✔ Stovebr✔ Ovenbr✔ Toasterbr✔ Blenderbr✔ Hot Water Kettlebr✔ Refrigerator/Freezer br✔ Dishwasherbr✔ Coffee Makerbr✔ Sink - Hot & Cold Waterbr✔ Platesbr✔ Glassesbr✔ Silverwarebr✔ Pots & PansbrbrBegin your day on the right foot by enjoying a delicious breakfast and a cup of coffee at the high table or the patio. And when it's time for lunch or dinner, the dining table provides the perfect setting to gather and enjoy a family meal.brbr✔ Dining Table with Seating for 5brbr★ SLEEPING ARRANGEMENTS – 2 BEDROOMS + LIVING AREA ★brTwo bedrooms offer the comforts needed to rest and relax after a fabulous day of soaking up the sun at Siesta Key Beach. Get those precious hours of sleep; tomorrow is a new and exciting day!brbr♛ Master Bedroom: King-Size Bed, Cozy Sofabr♛ Bedroom 2: Queen Size-Bed + Bunk Bed (Twin over Twin)br♛ Living Room: Double Sofa Bedbrbr✔ Premium Pillows, Linens, and Sheetsbr✔ Smart TVsbr✔ Closets with Hangers and Shelvesbr✔ Dressers with Spacious Drawersbr✔ Night Stands with Reading Lampsbr✔ Full-Size Mirrorsbrbr★ BATHROOM ★brThe townhome features two full bathrooms and a half bath to keep you fresh and rejuvenated. To ensure that you have a comfortable and carefree stay, we have provided essential toiletries and towels in each bathroom.brbr✔ Walk-In Showerbr✔ Bathtub with a Showerbr✔ Vanitybr✔ Mirrorbr✔ Toiletbr✔ Towelsbr✔ Hair Dryerbr✔ Essential Toiletriesbrbr★ PATIO ★brIf you want to take in the serenity of the outdoors but don't want to leave the comforts of the home, come to the private patio, a perfect setting for a refreshing drink!brbr✔ Cozy Seating Area with a ParasolbrbrIf you have any questions about our stylish home, please don't hesitate to ask. We'd be happy to assist in any way we can.brbrGuest access brbrThe townhouse is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. brbrOther than the already mentioned amenities, our home also comes with the following:brbr✔ High-Speed Wi-Fibr✔ Self Check-In (Smart Lock)br✔ Travel Crib (available through third party company paid for by the guest)br✔ Air Conditioningbr✔ Washer/Dryer + Detergentbr✔ Iron/BoardbrbrThe home is part of an upscale community with private access to the swimming pool area and the gated beach that you can freely use throughout your stay.brbr✔ Swimming Pool with Sun Loungesbr✔ Private Beach Access (Chairs provided by HOA)br✔ Free Parking (One Spot)br**NOTE - Unit comes with one designated parking spot at the back of the unit. In Front of the unit is 24 hour parking only. brbrOther things to notebrbr★ ADDITIONAL ACCOMMODATION ★brTraveling in a larger group, or your preferred dates are already taken You'll be happy to know that we offer additional accommodation in the community and the area. Feel free to browse our profile for a detailed list of fantastic stays.brbr★ CLEANING & SANITIZATION ★brHealth, safety, and well-being of our guests are of utmost importance. For this reason, we use a thorough cleaning process after each check-out.brbr★ NO PETS ALLOWED ★brWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable to accommodate them.brbr★ NO SMOKING INSIDE ★brPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbr★ NO PARTIES/EVENTS ★brWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits.brbrThank you very much for your understanding.brbrInteraction with guests brbrWe will be accessible 24/7 for our guests via phone, text, or the VRBO app. brExpect a quick and prompt response. We give our guests space but are available for every inquiry. brbrContact us now so we can begin arranging your perfect vacation!brbrThe neighborhoodbrbrOverviewbrbrThe townhouse is nestled on a private street with a gated beach access point in Siesta Key, a tropical haven on the west coast of Florida that embodies the essence of paradise—known for its powdery white sands, crystal-clear waters, and laid-back atmosphere.brbrSiesta Key is renowned for having some of the most breathtaking beaches in the United States. Siesta Beach, in particular, has earned acclaim for its powdery, quartz-crystal sands, which stay cool even on the warmest days. Sunset at Siesta Beach is a spectacle not to be missed, with hues of orange and pink painting the sky as the sun dips below the horizon.brbrBeyond the beaches, Siesta Key offers a wide range of outdoor activities. Kayak through the calm waters of the mangrove tunnels at South Lido County Park, paddleboarding in the Gulf of Mexico, or embark on a fishing charter to catch your dinner. Nature enthusiasts will appreciate the lush landscapes and wildlife in the nearby Myakka River State Park.brbrSiesta Key Village is the heart of the island's dining, shopping, and entertainment scene. Stroll along quaint streets with boutiques, surf shops, and art galleries. Savor fresh seafood at beachfront restaurants, sip tropical cocktails at vibrant bars, and enjoy live music under the stars.brbrThe warm waters surrounding Siesta Key beckon adventure seekers to explore. Try windsurfing, jet skiing, or parasailing for an adrenaline rush. Scuba diving and snorkeling enthusiasts will be delighted by the vibrant underwater world of the Gulf. For a more leisurely experience, rent a boat, explore the Intracoastal Waterway, or take a dolphin-watching tour.brbrCome and discover the beauty and tranquility of this coastal gem, where every day feels like a beach day in paradise.brbrHere are some places of interest you'll be looking to visit during your stay.brbr✔ Siesta Key Beach (3 min away)br✔ Crescent Beach (3 min away)br✔ PARASAIL SIESTA (4 min away)br✔ Siesta Key Watersports (5 min away)br✔ Siesta Key Village (5 min away)br✔ Marie Selby Botanical Gardens (15 min away)br✔ Sarasota Jungle Gardens (24 min away)br✔ Lido Key Beach (25 min away)br✔ South Lido County Park (25 min away)br✔ Mote Marine Laboratory & Aquarium (25 min away)br✔ St. Petersburg (55 min away)br✔ Tampa (1h 5 min away)br✔ Fort Myers (1h 15 min away)brbr***Distance times are calculated if traveling by car.brbrGetting aroundbrbrIf you arrive by car, you will be happy to know that we offer one free parking spot in the back of the townhouse. However, if you would like to avoid driving during your stay, there are many convenient, easily accessible transportation options close to our home.brbr✔ Siesta Key Breeze Trolley (stop on top of the street leads you to Siesta Key Village for free)br✔ Taxibr✔ Lyft & UberbrbrIf you are flying in/out of the area, the best way would be at the below airport:brbr✔ Sarasota Bradenton International Airport (25 min away)br

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

Siesta Key, Florida, United States

Bed

Bath

8

Sleeps

$312.38

A beautiful 3 bedroom 3 bathroom house situated in a quiet neighborhood in Siesta Key. This ideal location is minutes away from the beautiful beaches of Siesta Key and Siesta Village. Less than a mile to to grocery stores, restaurants, and shopping. The house has WIFI and Roku TV's. Fully stocked kitchen: pots, pans, utensils, new stainless steel appliances, coffee maker, blender, etc.). Large heated pool inside the 2 story lanai. Oversized two stall garage for parking, bikes, pool toys, beach necessities and a game room.

Siesta Key-Walk to the beach, private pool, fire pit

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$257.57

1225 Gulf and Bay Bayside by Tropical Sands Accommodations br brWelcome to 1225 Gulf and Bay Bayside! Experience the perfect blend of relaxation and adventure at this beautifully maintained three-level vacation home ideally situated within the Gulf and Bay Club Bayside community. This three-bedroom, two-bath retreat offers resort-style amenities, and a tranquil setting just minutes from Siesta Key Beach. Perfect for families or friends, this inviting property combines comfort, and outdoor recreation for a memorable Gulf Coast escape.br brHighlights br• 6-minute walk to Siesta Key Beach br• 3 Bedroom / 2 Bathroom br• 1 King, 2 Queens br• Desk for remote work br• 2 heated community pools br• Community fitness center  br• Tennis and pickleball courts br• Community Fishing dock br• Shared picnic area and walking path br• Washer and dryer br brThe private outdoor balcony offers a peaceful space to relax or dine, while the tropical decor creates a calming ambiance throughout the home. Enjoy resort style living with two heated pools, a fully equipped fitness center, and access to tennis and pickleball courts. Fish from the community dock or have a seaside picnic at the shaded tables. brbrThe main floor features a cozy seating area, a modern kitchen equipped with all essentials, and a stylish dining table perfect for family meals. Enjoy your favorite drinks at the bar with a drink fridge, then step outside to the screened-in balcony with an additional dining area. The split level design provides privacy with a primary bedroom downstairs and two guest bedrooms upstairs and tropical decor to enhance your comfort. br brThe primary bedroom located on the lower level offers a king bed, privacy, and comfort with a full bathroom featuring a walk-in shower. The upstairs bedrooms each have stylish decor, queen beds, and access to the hall bathroom, providing a restful environment for all family members or guests.brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower  br• Second Bedroom: Queen bed br• Third Bedroom: Queen bed br brGuests enjoy the convenience of a washer and dryer and access to the community pools, dock, tennis, and pickleball courts. Just minutes from Siesta Key Beach, shops, and local restaurants, this community offers everything for an effortless vacation.br brReserve your stay at 1225 Gulf and Bay Bayside today and indulge in a Gulf Coast vacation filled with water adventures, outdoor amenities, and island charm. Book now and start creating memories on Siesta Key! br brbr- brThis home is managed by Tropical Sands Accommodations.  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.

Beach Access, Pools, Tennis and Pickleball - 1225 Gulf & Bayside

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$293.27

Looking for a great location, close to the beach and village but still in a quiet and relaxing complex â€œ look no further! Our recently renovated, beautifully furnished, and spacious split level town home is right across the street from beautiful Siesta Key Beach â€œ known for its warm, clear water and white, powdery sand that never gets hot to the touch. Siesta Village, offering restaurants, boutique shops, night life and a grocery store, is less than a mile away â€œ a short drive or take the free trolley that stops right outside the complex every 20-30 minutes. Our home has over 1,300 cozy square feet with 10 ft. ceilings, separate dining and living areas, a one car garage (with additional parking available), stainless appliances, and a full size washer and dryer. The large living room opens onto a balcony overlooking a lake (with lots of turtles). The master bedroom opens onto the balcony too, has an en-suite bathroom, and a king bed. The second bedroom has an adjacent full bath and features two twin beds. Central air, free Wi-Fi, a well-stocked kitchen, and cable TV in the living room and each bedroom round out the amenities in the unit. When you are not relaxing in the town home, spending time at the beach, catching a spectacular sunset, or strolling in the village; play tennis, take a dip in the pool, or have a picnic using the development's facilities. Book today â€œ weâ„¢re sure you wonâ„¢t be disappointed!

Our House at the Beach C-112 Great Location, Spacious, Updated

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$311.33

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

Our House at the Beach C-108 Single Story, Private Entry

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$332.76

Our House at the Beach C-111 by Tropical Sands AccommodationsbrCondo in Siesta Key, FloridabrbrExperience the ultimate in coastal living at Our House at the Beach C-111, a beautifully furnished two-bedroom, two-bath condo located steps away from the stunning Siesta Key Beach in Siesta Key, Florida. This vacation rental perfectly blends comfort and convenience, making it an ideal choice for families and friends looking to enjoy the Gulf of Mexico. brbr Highlights br• 4-minute walk to the beach br• 2-minute walk to trolley stop br• Balcony with Water Views br• Washer and dryer br• TV in each bedroom br• 1 parking spot br• Community pool, BBQ Grills, and Two Tennis Courts brbrPrime Location and Easy Access: brWith a 4-minute walk to the beach and a 2-minute walk to the Siesta Key trolley stop, you’ll have effortless access to making a splash in the sparkling Gulf waters, relaxing on the soft, sugar sand beach, and exploring the vibrant atmosphere of Siesta Key Village, known for its diverse dining and live entertainment options. Don’t forget to check out the charming boutiques in the South Village Shopping District! brbrSpacious Beach Interior:brOur House at the Beach features a generous bi-level layout with separate dining and living room spaces, making it perfect for family gatherings or entertaining friends. The eat-in kitchen is fully stocked with pots, pans, dishware, and flatware, and it includes full-sized appliances such as a dishwasher, microwave, and washer and dryer for your convenience. brbrStep out from the bright, spacious living room to your private balcony, where you can breathe in the fresh air while overlooking beautifully landscaped grounds. The primary bedroom suite offers its own balcony, an ensuite bathroom, and a large closet with a dressing area, creating a personal retreat for relaxation. The second bedroom provides comfortable accommodations with an adjacent full bathroom, ideal for guests or family members. brbrUnforgettable Experiences Await:brBook your stay at Our House at the Beach C-111 today, where relaxation and adventure meet on the beautiful shores of Siesta Key, Florida! Experience unforgettable sunsets and create lifelong memories in this beach paradise.

Coastal Condo Steps from Siesta Key Beach - Our House at the Beach C-111

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$311.71

Midnight Cove II Unit 220D is ready for your upcoming getaway! This stunning three-bedroom condo offers the perfect blend of relaxation and adventure, located in the heart of Siesta Key, where the local community thrives with exceptional shopping, dining, art, and culture. Enjoy the convenience of the FREE Siesta Key Breeze Trolley, making your exploration effortless without the hassle of parking. Plus, with dedicated beach access just a short stroll away, you’ll be able to dig your toes in the sand and enjoy all that our beautiful beaches have to offer.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, Midnight Cove II Unit 220D offers a beautifully designed living space perfect for relaxation and togetherness. The inviting living room features plush seating and a large flat-screen TV, creating an ideal gathering spot after a day on the beach. The fully equipped kitchen boasts modern appliances, stunning granite countertops, and all the necessary cookware and utensils for family dining. The adjacent dining area comfortably seats six, making it easy to share meals and create lasting memories. The primary bedroom features a luxurious king bed, a spacious walk-in closet, and an ensuite bathroom complete with an updated walk-in shower. The second bedroom offers a cozy queen bed, while the third bedroom is perfect for kids with twin beds. A shared bathroom with a combo tub/shower provides added convenience for all guests.brbrWe can’t wait to welcome you to your new happy place!

Midnight Cove II 220D - Peaceful Bayside Vacation!

Siesta Key, Florida, United States

3

Bed

Bath

Sleeps

$311.33

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

Our House at the Beach C-102- Townhouse Near Beach and Pool!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$351.96

Step into paradise at Siesta Sweetheart, a charming island oasis designed for sun-soaked relaxation and unforgettable memories. True to its name, this beautifully appointed home steals your heart the moment you arrive. Whether you are planning a romantic escape, a fun family getaway, or a peaceful retreat with close friends, Siesta Sweetheart offers the perfect blend of coastal elegance and laid-back Florida charm with an open, airy layout filled with natural light, modern amenities, and thoughtful beachy decor. Nestled in a quiet, highly desirable neighborhood, you are just a short stroll from the powdery, quartz sands of Siesta Key Beach which is consistently voted one of the top beaches in America. When the sun goes down, walk or take a free island trolley ride into Siesta Key Village to explore vibrant boutique shopping, live music, and incredible local dining. Whether you want to spend your days hunting for sharks' teeth on the shoreline or paddleboarding through the mangroves, Siesta Sweetheart is the ultimate home base for your next getaway. You couldn't ask for a better spot!brbrPrimary-Ensuite with King Bed and full bathbrSecond Primary-Ensuite with queen bed and full bathbrBedroom 3-Queen Bed with half bathbrOffice with desk and trundle twin bed

Siesta Sweetheart: 3 BR, 2.5 BA House in Siesta Key, Sleeps 8

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1635.26

Summary:brbrWelcome to Between the Waves, a beautifully designed new construction vacation rental perfect for larger families or groups seeking a memorable getaway. With eight spacious bedrooms and 8.5 bathrooms, this upscale home is located just steps from the pristine beaches of Siesta Key and Siesta Key Village, which offers fun dining and shopping for all ages.brbrbrbrThe Space:brbrCheckout a 3D walkthrough of the home: https://www.zillow.com/view-imx/ee57a516-6fde-4708-9bd4-ae6635a51082 setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboardbrbrbrbrHighlightsbrbr• 2-minute walk to the beachbrbr• 2-minute walk to Siesta Key Villagebrbr• Brand new construction homebrbr• Rooftop deck with beach viewsbrbr• Private pool with in-ground spabrbr• Waterslidebrbr• Foosball Tablebrbr• Beach chairs and cartbrbr• Washer and dryerbrbr• Dog friendly with approval and additional feebrbrbrbrStep outside to your private oasis, featuring a private pool and an in-ground spa that offers relaxation, a waterslide for the kids, and a custom outdoor shower to rinse off after a day of beach adventures. Follow the stairs up to the rooftop deck for breathtaking beach views, perfect for sunset gatherings.brbrbrbrInside, the spacious living room welcomes you with modern furnishings with nautical touches. The gourmet kitchen boasts stainless steel appliances, a wine fridge, and a bar seating at the kitchen island. Enjoy formal meal at the indoor dining table or take it outside onto the balcony table overlooking the pool.brbrbrbrBetween the Waves' primary bedroom is a relaxing oasis with a gorgeous King suite and an ensuite bathroom with a walk-in shower and soaking tub. The additional 6 bedrooms are also appointed with King beds and ensuite bathrooms, and the 7th bedroom has a twin bunk bed with a total of 3 twin beds as well as an ensuite bathroom.brbrbrbrRoom Detailsbrbr-Primary Bedroom: King bed and ensuite bathroom with walk-in shower and soaking tubbrbr-Second Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Third Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Fourth Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Fifth Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Sixth Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Seventh Bedroom: King bed and ensuite bathroom with walk-in showerbrbr-Eighth Bedroom: Twin over Twin over Twin bunk bed and ensuite bathroom with walk-in showerbrbrbrbrDon't miss out on your chance to stay at Between the Waves! Book your dream getaway today and make unforgettable memories on Siesta Key!brbrbrbrOther Things to Note:brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply.brbrbrbrThis property has hosted many happy stays but is newly listed under GetawayClub management, an Anna Maria Island property management company. It is under transition from the existing management company so the review record is starting fresh. Please let us know if you have any questions.brbrbrbr4 cars maximum are 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.brbrbrbrPlease 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.

Between the Waves - Siesta Key Luxury Home

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$651.87

Escape to this welcoming house in picturesque Siesta Key. With four bedrooms featuring a king, queen, twin, and a sofa bed, guests find plenty of space to relax. Three bathrooms add convenience for everyone in your group. The living room offers a comfortable spot to unwind after a day of exploring. Climate control keeps the atmosphere just right, whether you want to cool down or warm up. This wonderful home invites guests to enjoy a peaceful and enjoyable stay. Experience what Siesta Key has to offer with a stay at our house.

Charming 4-bedroom house with AC in Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$387.61

Just steps from Siesta Key Village and a short walk to the world-famous Siesta Beach, this private canal-front home offers the perfect blend of island convenience and coastal tranquility. Tucked on a quiet street with no neighbors across the canal, the property feels secluded yet is only minutes from lively restaurants, beach bars, and boutique shops. With a heated pool, spa, boat dock, Tesla Level 2 EV charger and thoughtful amenities throughout, it’s designed to make every day of your stay effortless.brbrSpend your mornings sipping coffee by the canal as the sun rises, then roll your beach cart down to the sand to sink your toes into the softest white quartz sand in the country. After a day at the beach, return home to unwind in the heated pool, relax in the hot tub, or gather with family and friends around the fire pit. The boat dock makes it easy to bring your own boat or rent one locally, giving you direct access to the waterways and Gulf adventures right from your backyard.brbrInside, the open-concept living area welcomes you with plenty of natural light, comfortable furnishings, and modern updates that make the home as functional as it is inviting. Cook meals in the fully stocked kitchen, gather around the dining table, or stretch out on the sofa for a movie night with streaming on a large TV. With step-free access throughout, the layout is easy for all ages to enjoy.brbrThe property comes ready with everything you need for your island getaway, from fast Wi-Fi to beach gear, including chairs, a cooler, and a tow-behind bike cart for easy trips to the shore. Bicycles are provided, or you can take advantage of Siesta Key’s free trolley and tip-only golf cart rides for a car-free stay.brbrWhether you’re here to soak up the sun, explore the canals, enjoy Siesta Village’s vibrant nightlife, or simply relax by the pool in your own private oasis, this home makes it all possible. The combination of privacy, walkability, and well-appointed amenities is rare on Siesta Key — making this the perfect place for families, couples, or groups of friends to create lasting memories.

Private Home 2bed 2bath King Bed Spa

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$587.6

Welcome to the Tropical Oasis HousebrbrTucked away in a peaceful residential neighborhood, just minutes from the sandy shores of Siesta Key Beach and Village, this beautifully decorated 3-bedroom, 2-bathroom pool home is the perfect getaway for up to six guests. It’s a place where comfort meets relaxation, offering you a private oasis to unwind and feel at home.brbrFrom the moment you step inside, you’ll be greeted by warm, inviting spaces and a stunning wall-to-wall view of the outdoor patio and pool area. The sliding pocket doors open fully, allowing the gentle island breeze to flow through, creating the perfect blend of indoor and outdoor living.brbr The open floor plan is designed with cozy decor throughout, featuring soft, neutral tones, warm lighting, and thoughtfully chosen furnishings that create an atmosphere of comfort and charm. Fully stocked kitchen has everything you need to cook a delicious meal, while the cozy dining area seats six—perfect for sharing meals and making memories. The living room offers plenty of plush seating and a TV for movie nights. For book lovers, a cozy leather couch is perfect for curling up with a good read and a cup of coffee. 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.brbr AS A CONDITION OF RENTING THIS PROPERTY, GUEST AND MEMBERS OF THEIR PARTY AGREE TO RELEASE, INDEMNIFY, AND HOLD HARMLESS THE HOST AND ANY AGENT OF THE HOST FROM AND AGAINST ALL LIABILITY FOR INJURY TO THE GUEST AND TO ANY MEMBER OF THEIR PARTY INCLUDING ANY INVITEES RESULTING FROM ANY CAUSE WHATSOEVER.

Siesta Key House, Pool & Hot Tub, 1 mile to the beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1465.63

Experience ultimate coastal luxury in this 6BR, Pet friendly Siesta Key duplex! Just steps from the sun-kissed beach, this retreat offers two private units with splash pools, tiki hot tubs, and vibrant murals perfect for photos. Ideal for families, groups, and beach lovers, it blends relaxation, fun, and style. Book now for an unforgettable Gulf Coast getaway!brbr☀ Private Poolbr☀ Hot Tubbr☀ Easy Beach Accessbr☀ BBQ GrillbrbrThe spacebrStep inside this exceptional duplex and discover a bright, stylish escape with open living areas, fully equipped kitchens, and cozy bedrooms. Each home features private outdoor spaces with pools and tiki huts, making it perfect for enjoying sunny days, relaxing evenings, and quality time with loved ones.brbr★Your stay includes:brHere’s a quick glance at what makes this Siesta Key retreat special:br☀ 2 Private Unitsbr☀ 6 Comfortable Bedrooms + Sofa Bedsbr☀ 2 Living Roomsbr☀ 2 Fully Equipped Kitchensbr☀ Arcade & Foosballbr☀ Luxury Tiki Hot Tubs & Splash Poolsbr☀ #Instaworthy Muralbr☀ Smart TVsbr☀ Wi-Fibr☀ Free Parkingbrbr★ Living RoomsbrBoth living rooms provide stylish spaces to unwind and connect:br☀ Two Snug Sofas with Pillows (convertible to extra beds)br☀ Smart TVsbr☀ Chic Coffee Tables & Reading Lampsbr☀ Arcade Machinesbr☀ Foosball Table (in one unit)brbr★ Kitchens & DiningbrFully equipped kitchens with modern appliances let you cook with ease while enjoying time together:br☀ Microwave, Stove, Oven, Blender, Toasterbr☀ Coffee Maker & Hot Water Kettlebr☀ Refrigerator/Freezer & Dishwasherbr☀ Sink with Hot & Cold Waterbr☀ Plates, Glasses, Silverware, Pots & Pansbr☀ Kitchen Bars with Seating for 10brbr★ Bedrooms & Sleeping ArrangementsbrAll bedrooms are designed for comfort, relaxation, and restful nights after exciting beach days:br→ HOME #1 – 3 Bedroomsbr☀ Master Bedroom 1: Queen-Size Bed + Queen-Size Futonbr☀ Bedroom 2: Queen-Size Bedbr☀ Bedroom 3: Queen-Size Bedbrbr→ HOME #2 – 3 Bedroomsbr☀ Master Bedroom 4: Queen-Size Bed + Queen-Size Futonbr☀ Bedroom 5: Queen-Size Bedbr☀ Bedroom 6: Queen-Size Bedbrbr☆All bedrooms have these amenities:br☀ Premium Memory-Foam Mattresses, Sheets, and Pillowsbr☀ Smart TVs in All Bedroomsbr☀ Closets with Hangers & Shelvesbr☀ Dressers with Spacious Drawersbr☀ Nightstands with Reading Lampsbrbr☆All Four Living Room Sofas Convert to Queen-Size Beds if Needed.brbr★ BathroomsbrEnjoy spa-like comfort with four full bathrooms thoughtfully equipped for your convenience:br☀ Bathtub with Showerbr☀ Walk-In Showerbr☀ Vanity & Mirrorbr☀ Toiletbr☀ Towels & Hair Dryerbr☀ Essential Toiletriesbrbr★ Outdoor SpacesbrStep outside to private poolside havens designed for fun and relaxation:br☀ Luxurious Splash Poolsbr☀ Lounge Seating Areasbr☀ String Lightsbr☀ Unique Tiki Hot Tubsbr☀ Cozy Seating Areasbr☀ Vibrant Muralsbrbr★ Families, groups, beach lovers, and anyone seeking a colorful, fun, and relaxing Siesta Key escape—book now for an unforgettable stay!brbr★☆ Guest Attractions nearby in Siesta Key Beachbr☀ Siesta Key Craft Festival – 4 min walkbr☀ Sarasota Beach – 8 min walkbr☀ Sunset Beach – 8 min walkbr☀ Point of Rocks – 11 min drivebr☀ Turtle Beach – 14 min drivebr☀ Sarasota Art Museum – 18 min drivebr☀ Bayfront Park – 20 min drivebr☀ TPC Prestancia (Golf Club) – 20 min drivebr☀ Ted Sperling Park Nature Trail – 27 min drivebr☀ Quick Point Nature Preserve – 28 min drivebr☀ South Lido County Park – 28 min drivebr☀ The John and Mable Ringling Museum of Art – 29 min drivebr☀ Ca' d'Zan (Historical Museum) – 30 min drivebr☀ South Lido Key Beach Park on the Gulf – 30 min drivebr☀ Manatee Village Historical Park – 43 min drivebr☀ Palma Sola Botanical Park – 56 min drivebrbr★☆ Restaurants Nearby in Siesta Key Beachbr☀ Gilligan's Island Bar & Grill – 3 min walkbr☀ Lobster Pot Restaurant – 3 min walkbr☀ The Cottage – 3 min walkbr☀ Daiquiri Deck Siesta Key Village – 3 min walkbr☀ Summer House Resturant – 4 min walkbr☀ Siesta Key Oyster Bar – 4 min walkbr☀ Another Broken Egg Cafe – 4 min walkbr☀ Sun Garden Cafe – 4 min walkbr☀ Cafe Gabbiano – 5 min walkbr☀ The Old Salty Dog Siesta Key – 7 min walkbr☀ Clayton's Siesta Grille – 10 min drivebr☀ SPEARFISH GRILLE – 11 min drivebr☀ The Toasted Yolk Cafe – 14 min drivebr☀ Florence & The Spice Boys – 15 min drivebr☀ Casa Masa - The Landings – 17 min drivebrbr★☆ Airports in Siesta Key Beachbr☀ Sarasota Bradenton International Airport – 29 min drivebr☀ Hidden River Airport-22FA – 47 min drivebrbr★☆ Transportation Nearby Siesta Key Beachbr☀ Ocean Blvd @ Calle Miramar NB – 3 min walkbr☀ Ocean Blvd @ Avenida Madera – 4 min walkbr☀ Ocean Blvd @ Canal Rd SB – 4 min walkbrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N' Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026brbr☆ Free hop-on hop-off rides to top island attractions with two local services – 77 Siesta Islander and Bay Runner Trolleybrbr☆ The Breeze-local bus service – makes travel simple between Downtown Sarasota and Siesta Keybrbr★☆ Hospitals in Siesta Key Beachbr☀ SMH Urgent Care Center at Stickney Point Rd – 11 min drivebr☀ Sarasota Memorial Hospital – 14 min drivebr☀ HCA Florida Sarasota Doctors Hospital – 23 min drivebrbrOther things to notebr★ Additional Accommodation OptionsbrTraveling with a larger group or finding your preferred dates unavailable We offer an additional unit within the duplex, as well as other listings in the area. Please visit our host profile to view all available properties.brbr★ Pet-Friendly HomebrPets are welcome on this property. Please note that an additional cleaning fee may apply if excessive pet hair, stains, or odors are detected after checkout.brbr★ Rentals, Activities & ToursbrA list of Preferred Vendors is provided for convenient rentals, activities, and tours. Options include:br✔ Golf Carts br✔ Mopeds br✔ Mini Carsbr✔ Umbrellas br✔ Bikes (Daily/Weekly)br✔ Kayaks br✔ Paddleboardsbr✔ Fishing Chartersbr✔ Adventure Toursbr✔ Sunset Cruises br✔ Eco-ToursbrGuests receive 10% off all listed prices using a special code provided before check-in.brbr★ Cleaning & SanitizationbrYour safety is our priority. Our team follows a detailed cleaning and sanitization process after every checkout to ensure a spotless, hygienic stay.brbr★ No Smoking IndoorsbrSmoking inside the home is strictly prohibited. Evidence of indoor smoking will result in an additional fee for odor removal and deep cleaning.brbr★ No Parties or EventsbrTo maintain a peaceful environment and protect the home’s condition, parties and large events are not permitted.brThank you for your understanding and cooperation.

Stunning Haven: 2 Pools & Hot Tubs ~ Walk to Beach

Siesta Key, Florida, United States