Vacation Rentals By Owner In Siesta Key, FL

Welcome to the epitome of waterfront living on Siesta Key. Professionally managed by Gulf Coast Vacation Rentals and located within the prestigious Gulf & Bay Club Bayside, this first-floor condominium offers tranquil bay views and an exceptional blend of comfort, style, and relaxed coastal elegance.brbrAs you step through the front door, you're greeted by an airy and inviting open-concept living space adorned with tasteful coastal decor. The living area seamlessly flows into the dining space, creating the perfect setting for entertaining guests or enjoying quiet evenings with loved ones. Large windows allow natural light to flood the interior, while offering breathtaking views of the shimmering waters just beyond.brbrThe fully equipped kitchen boasts modern appliances, sleek cabinetry, and ample counter space, making meal preparation a delight. Whether you're whipping up a quick breakfast or preparing a gourmet dinner, this kitchen has everything you need to satisfy your culinary cravings.brbrThe primary bedroom is a sanctuary of comfort and relaxation, featuring a plush king-sized bed, ample closet space, and an en-suite bathroom complete with a luxurious walk-in shower. The second bedroom offers flexibility and convenience, with a day twin sized day bed and extra trundle bed that can easily accommodate family and loved ones. brbrStep outside onto your private patio and prepare to be captivated by the stunning waterfront vistas that stretch as far as the eye can see. Whether you're enjoying al fresco dining, lounging with a good book, or simply soaking in the serene surroundings, this outdoor oasis is sure to be your favorite spot to unwind.brbrResidents of Gulf and Bay Club Bayside enjoy access to an array of resort-style amenities, including a clubhouse, fitness center, tennis courts, and multiple swimming pools. With access to the pristine beaches of Siesta Key just a short walk away, every day feels like a vacation in paradise.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Gorgeous bay views from this ground floor Siesta Key Condo - GBB 1360

Siesta Key, Florida, United States

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$544.97

You will be close to everything when you stay at this centrally-located house. It's a 2 min drive Siesta Key village restaurants and shops. A 5 min drive or 20 min walk to the #1 beach in US. Supermarket, gas station and pharmacy within 5 min drive. Stocked with beach chairs, umbrellas, cooler, and floats. The pool area has a bbq, full size bar, TV and dining set for 8. The home has a high chair, pack and play, puzzles, books and toys. Trolley stop around the corner that takes you to the beaches, the village and downtown Sarasota. You will certainly enjoy your stay here! Only one booking allowed per 30 day period.

Family friendly Siesta Key home with heated pool. 5 minutes drive to beach.

Siesta Key, Florida, United States

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Bath

Sleeps

$188.65

Be the first to discover this gem!! No car needed for this trip! Your own piece of paradise at Jamaica Royale, steps from heated pool #1, while a mere two-minute stroll takes you to the pristine Siesta Key beach. Jamaica Royale's prime location on these dazzling white sands.. Assigned covered parking space just steps from your front door. Unit is generously equipped for your home away from home. The kitchen is fully stocked with a range of appliances, including a dishwasher. The spacious bedroom offers a brand comfortable King bed. A sleeper couch in the living room is also available. There's a washer/dryer for added convenience in the unit. 300-foot expanse of cool, powdery white sand beach. There are two Tiki huts to retreat to. Our property boasts two BBQ grills. With three heated pools, there's plenty of space for everyone to unwind. The private beach area features exclusive lounge chairs for JR guests, and you can also arrange for private cabanas through the JR office.

Siesta Key Jamaica Royale Retreat

Siesta Key, Florida, United States

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Bath

Sleeps

$892.89

Beach Palm Villa | Heated Pool + Walk to Siesta Key Beachbrbr Why You'll Love This HomebrImmerse yourself in coastal luxury at Beach Palm Villa, a private Siesta Key retreat just a short stroll from world-famous Siesta Key Beach. Designed for effortless comfort and style, this 4-bedroom oasis combines resort-level amenities with the relaxed rhythm of island living. From poolside lounging to family dinners under the stars, every moment here feels like a treasured memory in the making.brbr ‍ ‍ Perfect ForbrMulti-generational families, friend groups, or couples seeking a luxurious island escape within walking distance to the beach.brbr ️ Imagine ThisbrYou wake to the sound of rustling palms and the promise of another sun-filled day. Brew a cup of coffee in the gourmet kitchen and step outside to your private heated pool, where the morning light dances across the water. Spend your day soaking in the sun, strolling to Siesta Key Beach just 10 minutes away, or perfecting your short game on the outdoor putting green. As evening falls, laughter fills the air around the fire pit while the sky glows in shades of coral and gold. Here, every detail invites you to relax, reconnect, and make lifelong memories. The heart of Beach Palm Villa is its modern, fully equipped kitchen, perfect for culinary creativity and casual gatherings alike. Enjoy regular and Keurig coffee makers, a dishwasher, stainless-steel appliances, and a water purification system that ensures every sip and ingredient is as refreshing as the Gulf breeze. With plenty of prep space and elegant design, cooking here feels effortless and inspiring.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, TVbr• Bedroom 2: King Bed, Shared Bath, TVbr• Bedroom 3: Queen Bed, Shared Bath, TVbr• Bedroom 4: Two Twin Bunk Beds with Trundles, Shared Bath, TVbrbr Explore the Areabr• 0.5 Miles (10-Minute Walk) to Siesta Key Beachbr• 0.7 Miles to Siesta Key Village – Dining, Shopping, and Nightlifebr• 7.0 Miles to Downtown Sarasota – Arts, Culture, and Entertainmentbr• 9.6 Miles to St. Armands Circle – Upscale Boutiques and Restaurantsbr• 11.5 Miles to Sarasota-Bradenton International Airport (SRQ)brbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.

Beach Palm Villa | Private Heated Pool, Fire Pit, Putting Green, & Spacious Outdoor Lounging Area

Siesta Key, Florida, United States

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Bath

Sleeps

$643.91

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, a guest bedroom offering two twin size beds as well as a sofa bed in the living area. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Apartment

Island House Beach Resort 14N

Siesta Key, Florida, United States

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Bath

Sleeps

$307.93

Walk to siesta beach from this stylish village house. Perfect for couples and group trips. The home is in a central location on Siesta key. Walking distance to Siesta Key village and beach access 7 (less than 1/2 mile).Enjoy the oversized private patio and with garden views or hop on a bike to siesta beach in less than 5 minutes. Both Siesta Key village and Beach access 7 are less than 1/2 mile from the home. Bikes available onsite ($40 per bike per stay by ven.)Unique and newly redesigned ground level unit. Lovely wood floors and a kitchen with an electric stove, microwave and full size refrigerator. Accommodates 2-5 guests with 2 bedrooms & 1 bath, and a couch bed. It is located on the ground level of the home with slider doors that open to a spacious patio and backyard. Please note there is a separate rental unit above, with a separate entrance . There is a washer and dryer at the entrance located in the garage that is shared and available for use from 3-8 pm daily. **Beach Gear items include only towels at this time.** beach cruiser rental please give 24 hour notice. Bikes are located onsite and a waiver and fee will be required.20 minute drive to Sarasota/Bradenton airport.All spaces are private, laundry is shared and available from 4-9 pm dailyBy air Bnb messengerSiesta keys village,

[escape to paradise] siesta key beach getaway

Siesta Key, Florida, United States

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Bath

Sleeps

$173.36

Experience the beauty of Siesta Key when you and your whole beach-loving crew stay at this fabulous 2-bedroom, 1.5-bathroom vacation rental at Midnight Cove II. Located just steps from the bay and the Gulf of Mexico, this 900-square-foot condo boasts views of the intracoastal waterway, private beach access, a community pool, and much more! Whether you spend your days sunbathing in the sand or luxuriating on your furnished balcony, you're sure to fall in love with this Sunshine State sanctuary.brbr-- THE PROPERTY --brbrFree WiFi | Community Grilling Area | Central A/C | 2.7 Miles to Siesta Village PlazabrbrLive like it's summertime every day at this beautiful beachside condo with its sunny location, stunning views, and inviting atmosphere.brbrBedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Living Room: Sleeper Sofa brbrCOMMUNITY AMENITIES: Clubhouse, heated pool, tennis & basketball courts, fitness center, boat dockbrOUTDOOR LIVING: Furnished balcony, dining set, lounge furniture, bay viewsbrINDOOR LIVING: 2 flat-screen TVs w/ streaming services, DVD player, stereo, dining table brKITCHEN: Fully equipped, drip coffee maker, hot water pot, stainless steel appliances, pots & pans, cooking utensils, ice maker, microwave, toaster, toaster oven, dishware & flatware, breakfast barbrGENERAL: Central heat, complimentary starter toiletries, beach chairs & towels, in-unit washer/dryer & additional coin laundry facilities in buildingbrFAQ: Stairs required to access the 3rd-floor unit, no elevator access, single-story interior brPARKING: Carport (1 vehicle)brbr-- THE LOCATION --brbrBEACHES: Crescent Beach (0.3 miles), Siesta Key Beach (1.7 miles), Sarasota Beach (2.6 miles), Lido Key Beach (10.6 miles), Manasota Key Beach (22.2 miles)brTEE TIME: Village Green Golf Club (5.6 miles), The Palms Golf Club at Forest Lakes (6.5 miles), Rolling Green Golf Village (9.6 miles), The Highlands Golf Course (10.6 miles), The Groves Golf Course (10.6 miles)brTHINGS TO SEE + DO: Siesta Village Plaza - bars, restaurants, shopping (2.7 miles), Marie Selby Botanical Gardens (6.4 miles), Sarasota Jungle Gardens (10.0 miles), The John and Mable Ringling Museum of Art (11.0 miles), Ca’ d’Zan (11.5 miles), Riverwalk (19.7 miles)brFAMILY FUN: Bayfront Park (7.2 miles), Big Cat Habitat Gulf Coast Sanctuary (11.2 miles), Mote Marine Laboratory & Aquarium (11.2 miles)brAIRPORTS: Sarasota Bradenton International Airport (11.1 miles), Tampa International Airport (69.6 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property is located on the 3rd floor and requires stairs to access. As there is no elevator available, this area may be difficult for guests with limited mobility

Siesta Key Condo: Resort Amenities, Walk to Beach!

Siesta Key, Florida, United States

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Bath

Sleeps

$5188.47

Your cozy getaway awaits in Siesta Key at this beatiful vacation rental. With 7 bedrooms, 2 kitchen, game room, theater room, 5 bathrooms and 2 family room. brPrivate pool and 2 minutes walking to Siesta key beach. This tranquil retreat is perfect for guests looking to unwind. Kickback, relax, and enjoy everything Siesta has to offer.

Walk to Siesta Key Beach!

Siesta Key, Florida, United States

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Bath

Sleeps

$421.07

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrModern Luxury in the Heart of Siesta Key Village! brbr brbrCome experience this beautifully reimagined condo in the heart of Siesta Key Village! This prime location puts you steps from Siesta Key’s best restaurants, boutique shops, and vibrant nightlife—all while being just an 8-minute walk from the world-famous Siesta Key Beach, ranked #1 in the U.S. and #4 in the world. brbr brbrLOCATION HIGHLIGHTS: brbr- Heart of Siesta Key Village brbr- Steps to restaurants, shops, and nightlife brbr- 8-minute walk to Siesta Key Beach brbr- Multiple beach access points brbr brbrPROPERTY FEATURES: brbr- 2 bedrooms/ 1 bathroom ground floor condo (891 sq ft) brbr- Resort-style heated community pool brbr- In-unit washer and dryer brbr- Pet-friendly (approval & fee required prior to booking) brbr brbrLIVING ROOM: brbr- Large Smart TV, new coaches brbr- Open concept layout brbr- Access to patio via glass sliders brbr brbrKITCHEN AND DINING: brbr- Modern appliances with brand-new cabinetry and countertops brbr- Dining table for 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, Smart TV, closet brbr- Guest bedroom: queen bed, Smart TV, closet brbr- Fully renovated bathroom, walk-in shower, spacious vanity brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: beach cart, a couple of beach chairs, beach umbrella, and beach towels brbr brbrIMPORTANT INFO: brbr- Street parking, first-come, first-served brbr- No oversized vehicles, trailers, or RVs brbr- No smoking or vaping inside brbr- Maximum occupancy 4 guests brbr brbrWITH A FRESH, MODERN RENOVATION AND AN UNBEATABLE SIESTA KEY LOCATION, THIS IS YOUR PERFECT BEACH RETREAT!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.brbrAll pets must be approved. For approved pets, there is a nonrefundable pet fee. For bookings 6 nights or less, there is a pet fee of $50/day plus processing fee and taxes. For bookings 7 nights or more, there is a pet fee of $300 plus processing fee and taxes. Make sure to pick up after your dog.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

In the heart of Siesta Key Village | Walk to Beach | Dog Friendly | Fully renovated & remodeled

Siesta Key, Florida, United States

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Bath

Sleeps

$612.77

Bayside Escape | Water Views, Walk to Siesta Key Beach, Balcony & Community PoolbrbrWhy You'll Love This HomebrBayside Escape offers a comfortable Siesta Key retreat just 0.6 miles from Siesta Key Beach, with easy access to both the shoreline and nearby dining in Siesta Key Village. Positioned near the Intracoastal, this home features a private balcony with water views, creating a relaxed setting to start and end your day. In addition to beach access, guests can enjoy a community pool located nearby, offering another option for cooling off or spending time outdoors. With a private garage, beach gear provided, and convenient access to the free island trolley, getting around the island is simple and flexible.brbrPerfect ForbrFamilies, couples, or small groups looking for a well-located Siesta Key stay with water views, beach access, and convenient amenities.brbrImagine ThisbrStart your morning on the balcony with coffee as boats move along the Intracoastal. Grab the provided beach gear and head out for the short trip to Siesta Key Beach, where the day unfolds on the sand and in the water. After time at the beach, return home to relax or take a short walk to the community pool for an afternoon swim. Spend the rest of the day at your own pace, whether that's exploring the island using the free trolley or stopping by Siesta Key Village for a casual meal or shopping. As evening settles in, head back to the balcony to unwind or gather indoors for dinner before settling into your private sleeping spaces.brbrWhere You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: King Bedbr• Bedroom 3: Two Twin BedsbrbrAccommodates up to 6 guests.brbrExplore the Areabr• 0.6 Miles to Siesta Key Beach – Powdery White Sand and Gulf Swimmingbr• 1.7 Miles to Siesta Key Village – Dining, Shopping, and Entertainmentbr• 6.5 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurantsbr• Nearby Intracoastal Waterway – Scenic Views and Boating ActivitybrbrDon't WaitbrYour reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.brbrNeed to KnowbrThis is a multi-level unit and does not have elevator access. If you need assistance bringing large items upstairs, please let us know and our team will be happy to help.brStarter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included.Please contact us directly for more information regarding any shared spaces associated with this property. The community pool is seasonally heated.

Bayside Escape | Water Views, Walk to Siesta Key Beach, Balcony & Community Pool

Siesta Key, Florida, United States

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Bath

Sleeps

$988.75

THIS IS THE HOUSE YOU'VE BEEN LOOKING FOR!! Relax, bring your suits & sunscreen we supply everything else for your dream vacation! Located steps away from one of the World's Best Beaches & a quick bike ride to Siesta Village. 4 bedrooms, 3 baths, heated pool, outdoor shower, & all the amenities of your own home. Perfect for families & restful getaways!brbrAlso includes free WIFI, smart TV's, & a fully stocked kitchen & laundry room.brbrFish, Kayak, boat or Paddle Board from our own private dock

Relaxing Canal Home, just 2 blocks from Beach!

Siesta Key, Florida, United States

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Sleeps

$237.82

Find your own oasis within this cozy villa that is perfectly located across the street from the Siesta Key beach, #1 rated beach in the US. If you need a break from the beach, you can relax by the pool that is located directly behind the villa. brbrAt the villa you will find everything that you need for your vacation, including; Kuerig coffee maker, cooking utensils, suntan lotion, soups, pool floats, bicycle, and many more!

Cozy Siesta Key Beach Villa

Siesta Key, Florida, United States

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Bath

Sleeps

$238.2

Parrot Beach Cottages Suite #1brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the best of Siesta Key mere steps from sugar-white sand and emerald waters here at Parrot Beach Cottages! Suite #1 is approximately 315 square feet - a small, fully furnished, studio-style suite that's ideal for up to two people. You'll have a king-size bed, a small full kitchen, and a tiny bathroom that consists of a single sink, a toilet, and a stand-up shower (but no bathtub). Ideally located on the ground floor of the complex next to the shared swimming pool, the suite also comes with one reserved, off-street parking spot for your ease and convenience.brbrThis studio is mere steps from one of the top white sand beaches in the world. In fact, beach access is so close, you'll hear the waves from home base! This area of the beach is a favorite for sunbathing, swimming, romantic sunset walks, small beach weddings, skim boarding, paddleboarding, kayaking, shore fishing, and much more. Fishermen catch everything from snapper and mackerel to snook and jacks. You'll be within walking distance of a number of businesses that rent all sorts of gear, from kayaks and paddleboards to bikes and video game systems. Due to how close the complex is to the beach, several rental outfitters will bring kayaks, paddleboards, and bikes right to the property and pick them up when you're done!brbrThe studio is also within easy walking distance of Siesta Key Village, where you'll find shops, restaurants, live music, and more. Or, head into town for other local adventures, including the world-renowned Ringling Museum, the Marie Selby Botanical Gardens, Mote Marine, Jungle Gardens, and outdoor shopping and dining on St. Armands Circle.brbrThings to know:brThere are three other suites available to rent at the Parrot Beach Cottages fourplex - Suite #2, Suite #3, and Suite #4brFree high-speed WiFibrSmoke-free propertybrSmall full Kitchen (without a dishwasher)brBedroom/living room space is small with only a few feet on each side of the bedbrThe suite has limited storage (one small closet)brFlat path to the front door; step-free access to the home, common area, bathroom, and bedroombrThe shower features grab barsbrSnowbird-friendly; please contact us for detailsbrPlease note that the shared pool is small, about 15 feet by 10 feet and about four to six feet deepbrThe overall property is very small, so there is no extra vehicle or visitor parking. There's also no nearby on-street parking. Guests love the location (truly walking distance to the beach and the village) and the more private feel of the beach, since this is a dead-end road and there is no nearby public parkingbrThere is a new home being built on the lot next door. Construction work is permitted by Sarasota County daily from 7:00am to 7:00pm.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 1.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Apartment

Beach Getaway Steps from the Sand w/ Shared Pool, Fast WiFi & Parking

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$289.45

We 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.brbrAbsolutely gorgeous views of the Gulf of Mexico from the balconies are just one of the many features ...you will enjoy staying in this vacation home. Sitting in the living areas of this home you are overlooking the sights of Siesta Key. The openness of the floor plan allows for entertaining, family dinners and a sense of togetherness. 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 QUEEN BEDSbrbr- Bed Size 3rd Rm: Pack & Play Availablebrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: TILE KIT, CARPETbrbr- Walk in shower: Yesbrbr- Parking: Yesbrbr- Parking Space Type: CARPORT 41brbr- Electric Stove: Yesbrbr- View: ISLAND VIEWbrbr- PICKLEBALL: Yesbrbr- Island View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 402

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$288.37

Welcome to Siesta Key # 407brbrWe 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 Canal and Intercoastal Waterway. 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 QUEENSbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 4brbr- Internet Access: WIFIbrbr- Parking: Yesbrbr- Parking Space Type: UNCOVEREDbrbr- Electric Stove: Yesbrbr- View: Baybrbr- PICKLEBALL: Yesbrbr- Bay View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 407

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$282.06

Designer decorated two bedrooms, two bathrooms 6th floor condo on the Gulf side steps away from America's #1 beach, Siesta Key Beach in Peppertree Bay. brbrThis lovely condo features a dining table with comfortable wicker chairs for six guests, a lovely sectional sofa, and a barrel chair in the living room for relaxing by the television or entertainment. Spacious lanai open to the living space with a fold-out sofa, game table, and a glass top table with chairs for morning coffee facing the intercoastal and sunrise. The master bedroom has a king-size bed with a large dresser and nightstands and an ensuite bathroom. The master bedroom sliding doors open onto the east-facing lanai. The guest room has a full-size bed with an ensuite bathroom. The guest bedroom also has a desk and has a view of the gulf. A fully equipped kitchen, three televisions (70, 55, and 40), high-speed internet, and wi-fi. brbrThe building offers secured entry, elevators, shopping carts for ease of transporting groceries to the unit, and a parking garage with an assigned parking spot conveniently located in front of the elevators. The storage locker assigned to the parking space has a beach wagon, four beach chairs, two umbrellas, four ocean noodles, and a 10 x 10 pop-up canopy for long days on the beach. brbrVisit beautiful Siesta Key Village restaurants and shops on the free shuttle bus which stops right in front of Peppertree Bay.brbrPeppertree Bay property has 24/7 security on-site. Shared spaces include two heated pools, tennis/pickleball courts, an exercise room with a sauna, two clubhouses, outdoor dining areas, community grills, and a beautiful private beach with chairs and chaise lounges. brbr**Peppertree Bay requires reservations for a minimum of 30 days. Ideally, we are looking for reservations of 2-6 months. Note that during the season months of January-March, reservations must begin and end at the end of the month.

1125-607 Peppertree Bay Condo-2BR / 2BA

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$326.73

brbrWelcome to this amazing 2 bedroom 2 bathroom condominium located at the Anchorage Yacht and Tennis Club in beautiful Siesta Key, Florida. Absolutely gorgeous views of the Gulf of Mexico and the sunset from the balconies in this vacation home are just one of the many features you will enjoy while staying here. This 8th floor unit is a perfect place to relax and rejuvenate!brbrThere is plenty of space for everyone to call theirs in this two bedroom unit. The master bedroom boasts a king bed, a walk-in closet and its own dressing area and bathroom while the guest bedroom has 2 full size beds with a connecting bathroom. Sitting in the living areas of this home you are overlooking the sights of Siesta Key. The sliding glass doors open to create an indoor/outdoor room that allows you to enjoy the breathtaking views and the warmth of Siesta Key. The kitchen here is fully stocked and allows you to make all your meals right in the comfort of your home spending more time gazing at the Gulf.brbrWhile you enjoy the breathtaking views, be sure to enjoy all the Anchorage Yacht and Tennis Club has to offer as well! A pool, tennis and pickleball courts, grilling area and a place to relax overlooking the intercoastal waterway and so much more await you. A short walk leads you to the Anchorage Yacht and Tennis Club's private access to the beach and the Gulf of Mexico. Restaurants and shopping abound within walking distance as well. 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 QUEENSbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: 8thbrbr- Internet Access: WIFIbrbr- Walk in shower: Yesbrbr- Parking: Carport/Coveredbrbr- Parking Space Type: 79brbr- Electric Stove: Yesbrbr- View: Gulfbrbr- PICKLEBALL: Yesbrbr- Gulf View: PARTIALbrbr- Island View: Island Viewbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 802

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$339.74

Stunning direct beach views of Siesta Key! This 3-bedroom condo at Gulf and Bay Club is the perfect place for that home away from home. Relax on your large balcony or sit on the beach voted #1 in the USA! The beautifully landscaped property has 3 pools, 6 tennis/pickleball courts, fitness center, dry saunas, and private beach access for you to relax and enjoy your time on your island getaway. Located centrally on the island, this property is perfect for experiencing the entire island. Travel to the south to the Crescent Village, or take a trip north to the Siesta Key village. Either direction you go, you’ll be surrounded by wonderful shops and restaurants, perfect for hours of endless fun. Just bring your sunscreen, bathing suit, flip-flops and have an unforgettable vacation!brbrBedroom 1: KingbrBedroom 2: 2 QueensbrBedroom 3: 2 TwinsbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,000

3bed Beachview condo w/ 3 pools on Siesta!

Siesta Key, Florida, United States

3

Bed

Bath

8

Sleeps

$396.79

Welcome to your perfect Siesta Key escape at Harbor Towers Yacht & Racquet Club, a beloved bayside community offering resort-style amenities and an unbeatable location. brbrThis beautifully furnished condo is designed for comfort in an upscale complex with tennis, a fitness room, sauna, heated pool and hot tub. This bayside community has fishing, boating, kayaking and more. Ideal for couples, families, or friends looking to experience the very best of Siesta Key.brbrHarbor Towers Amenities Include:br*Heated bayside swimming pool and hot tub br*Tennis courtsbr*Fitness center and saunabr*Community room with full kitchen, piano and pool tablebr*Organized community activitiesbr*Gas grills for outdoor cooking with plenty of outdoor tables and chairsbr*Fishing pierbr*Bayside and poolside loungers, and a shaded gazebobrbrInside, the condo feels warm and welcoming with stylish coastal décor and thoughtful touches throughout. The living area features a large, plush sectional, perfect for movie nights, afternoon naps, or gathering after a day at the beach. Just off the main living space, the cozy sunroom invites you to unwind with a morning coffee or evening cocktail while soaking in the Florida sunshine. The bedrooms offer comfy beds dressed in high-end linens, ensuring restful nights after days filled with adventure.brbrThe fully equipped kitchen makes dining in easy, whether you’re preparing a quick breakfast before heading out or cooking a full meal to enjoy at home. With quality cookware, ample counter space, and all the essentials, it’s as functional as it is inviting. You’ll also find beach essentials provided, so your days on the sand are stress-free and fun.brbrAdditional Amenities br- 2 Minutes from Top-Rated Siesta Key Beachbr- Fully Stocked Kitchenbr- High-End Furnishingsbr- High-Quality Linens & Turkish Beach Towels br- Ensuite Bathroom with Plush Towels br- Private Screened-in Balcony br- High Speed Internetbr- Smart TVs and Streamingbr- Free TrolleybrbrStep outside the condo and discover everything that makes Harbor Towers so special. This vibrant waterfront community is known for its extensive amenities and friendly atmosphere, offering something for everyone.brbrOne of the biggest highlights is the location. Siesta Key and Crescent Beach are just 2-minutes away. Hop on the free Siesta Key trolley, which stops nearby and runs throughout the island, making it easy to explore multiple beach access points and spend time in Siesta Key Village with its charming shops, restaurants, and nightlife.brbrWhether you’re here to relax, explore, or do a little of both, this Harbor Towers condo offers the perfect home base for an unforgettable Siesta Key vacation.

Upscale Complex Near Beach and Bay with Tennis, Fitness Room, Pool, Hot Tub

Siesta Key, Florida, United States

Bed

Bath