Vacation Rentals By Owner In Siesta Key, FL

Palm Island Life | Heated Pool, Fire Pit + 0.3 Miles to Siesta Beachbrbr Why You'll Love This HomebrSlide open the glass doors and step into your very own canal-front sanctuary—complete with a screened heated private pool, fire pit and lanai. Nestled in the exclusive Palm Island neighborhood of Siesta Key, this home balances serene waterfront living with quick walkability to the world-famous white sands of Siesta Beach (0.3 miles) and vibrant dining at Siesta Key Village (0.4 miles).brbr ‍ ‍ Perfect ForbrIdeal for boating enthusiasts, families, couples, or adult groups seeking a private coastal experience with premium indoor-outdoor flow and nearby walkable attractions.brbr ️ Imagine ThisbrWake up to sunlight pouring into your primary suite, grab a coffee from the kitchen, and stroll just 0.3 miles to Beach Access 10 for a morning barefoot walk on Siesta's famous quartz sands.brbrReturn for lunch by the pool, fire up the grill, or sway in the backyard hammock under palm shade. In the evening, gather around the courtyard fire pit or head to the Village for live music and island cocktails—all within walking distance.brbrInside, the home's tile flooring, granite countertops, and stainless appliances create a bright, coastal-modern feel. With seamless indoor-outdoor flow, you're never far from a breeze, a view, or your next relaxing moment.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Ensuite Bathroom, TVbr- Bedroom 2: Queen Bed, Shared Hall Bath, TVbr- Bedroom 3: Twin over Full, Shared Hall Bath, TVbr- Additional Sleeping: Air Mattress, Sleeps 2brbr Explore the Areabr- 0.3 miles to Siesta Beach (Access 10)br- 0.4 miles to Siesta Key Village – Boutique shopping, live music, seafood, coffee shopsbr- Easy access to water sports rentals, boat charters, and nature trailsbr- Peaceful residential feel with the energy of coastal living just minutes awaybrbr Need to Know: Free High-Speed WiFi. This pool is heated between November 15 - April 15. Single-Level Home - No stairs inside the home. Dog Friendly, Up to 25 lbs., with an Additional Fee.

Palm Island Life - Heated Pool, Canal Front, Fire Pit, Walk to Siesta Beach

Siesta Key, Florida, United States

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Bath

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Exceptional(87)

$766.78

Luxury Beachside RetreatbrbrWelcome to your Siesta Key escape, just steps from the famous Public Beach. This spacious 1,850 sqft 3BR/2.5BA townhouse invites you to relax with two king bedrooms and a romantic loft featuring a queen bed, private balcony, and breathtaking Gulf views.brbrWake up to the ocean from all three balconies, each offering beautiful beach views. Spend your days by the heated lagoon-style pool (heated during cooler winter months) shared by only two duplexes. Enjoy beach chairs, umbrellas, free Wi-Fi, and parking for 2–3 cars.brbrAn unbeatable location for your perfect Siesta Key getaway.

⭐️ Luxury Coastal Retreat, 60 Steps to World-Famous Siesta Key Beach! ⭐️

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(2)

$259.9

Florida charm awaits you just a short stroll to Siesta Key Village for shopping or casual and fine dining and a few minutes to world famous Siesta Key Beach! This unique property has a lot to offer. brbrSecond floor Condo with Natural lighting abounds through wall to wall sliders in all rooms and leads to two generously sized lanais with views of both nature and water. Enjoy the pool with grilling area and some of the best views and fishing behind the historic Buster Brown clubhouse with guest house, where the gulf and bay merge. Swim and see all types of nature at the private beach, just a short walk from condo. Great fishing off the pier too! Take in nightly sunsets and views of the downtown Sarasota skyline or a kayak trip right from the private pier with private beach area with Gulf access. Condo is completely updated and impeccably designed fresh Florida feel. With updated kitchen and a hidden stackable washer and dryer.brThis special condo will have you feeling like you have arrived in paradise!brbrPlus two beach chairs, umbrella and sun shade

Hidden Sandy cove walking distance to village

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(9)

$592.8

Welcome to Surfside! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5 bathroom home sleeps up to 6. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized balcony for enjoying that island breeze, and a large kitchen with plenty of space to cook in. The second living level has 3 bedrooms, 2 full baths, a washer and dryer, and another balcony off the bedrooms. This home is equipped with 2 parking spaces: 1 in the drive way and 1 carport space in the rear. For your convenience, there is an onsite beach access path that will lead you to the sugary sands and crystal-clear waters. This home is just a short stroll to the Siesta Key Village with a large variety of dining and shopping options. Capture your piece of paradise with this fabulous Siesta Key townhome.br*Stairs only. All guests must have the ability to use stairs.brbrBedroom 1 - KingbrBedroom 2 - KingbrBedroom 3 - QueenbrbrAdded 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: 27br*Security Authorization Hold taken upon check-in. Amount: $1,000

Stunning 3 Bedroom with Beach Access!

Siesta Key, Florida, United States

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Bath

Sleeps

$398.78

Summary:brbrIndulge in a luxurious stay at this completely renovated home in the center of the island, offering a private pool and a tranquil atmosphere. , you can immerse yourself in the beauty of this home. This home is ideal for families with children and infants, providing a perfect blend of comfort and convenience. Small dog allowed with pet fee. No smoking. Month minimum stay booked by the calendar month.

Apartment

Siesta Key Pool home 5239 Winding Way

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(78)

$387.1

Please, Saturday - Saturday rentals only. brSATURDAY - SATURDAY RENTALS ONLYbrWelcome to Siesta Key! Come, relax and take in the top floor views of the #1 rated beach in the United States. The condo was professionally designed to accentuate your “beach time”. Enjoy the updated decor, furniture, king bed, and fully equipped kitchen complete with Keurig single serve/carafe combo coffee maker. All linens are provided including sheets, towels, beach towels, beach chairs and umbrella. There are two cable tv's, and WiFi for internet access. The patio offers top of the line Ratan lounge chairs and a love seat so you can relax and enjoy the 180 degree view of the beach.brbrEnjoy the wonderful full-size pool right outside your back door. Elevator Access to our top floor condo with the fabulous view. Coin operated laundry located on every floor of each building, Reserved parking spot; outdoor grills and shuffleboard fun are waiting. Walk through the Siesta Key Village where shopping and dining options are everywhere and only minutes from your home. If you are in the mood to explore, Sarasota has many fine art galleries, upscale shopping, dining, golf, theatre, sunset dinner cruises and sailing on the Gulf.brSaturday-Saturday rentals only please. 7-day minimum.

Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(17)

$292.96

This coastal, two bedroom, two bath condo offers everything you need for a relaxing stay. It is located on beautiful Siesta Key, with the number one voted beach in the USA. There is a fully equipped kitchen where you can prepare family meals. The comfortable living room is furnished with a large screen tv and free WiFi. Enjoy sitting on the lanai overlooking the resort-style swimming pool. Just a short walk to the beach, it’s perfect for couples, families, or friends looking to unwind in the sun. brbrThe spacebrOur condo is located on the second floor and overlooks the heated pool. You’ll have full access to the entire space during your stay. Please note that two interior closets are locked and reserved for the owners. The beach supplies closet is conveniently located on the lanai, with chairs, umbrella, and beach wagon. Also includes fishing gear for fishing in the Intercoastal waters off the pier.brbrGuest accessbrYou have access to the entire condo except for two small closets. Full access to clubhouse and swimming pool.brbrOther things to notebrFull streaming 4k TV's are available in 3 rooms but logins are not provided. You are welcome to login to your own accounts. A small dedicated workstation for those who need to conduct business.brbrWe are a 13 minute walk to the closest public beach access, which is #12, brCrescent Beach and a 5 minute drive to the Main Siesta Beach access with large parking lot and restrooms.brThe Breeze trolley picks up at our condo and takes you everywhere on Siesta Key, including restaurants, all beach access points, shopping, etc.brbrWe do require you to be 25 yrs. of age to reserve our condo.

Sunny Beach Retreat on Siesta Key

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(13)

$353.59

Walk out your door to enjoy all the Siesta Key white sands have to offer. This 1-bedroom, 1.5-bath unit is ready for your immediate enjoyment. Enjoy vaulted beamed ceilings throughout, and a fully equipped kitchen conveniently, open to the dining nook and living room areas. The living room features a new pull-out queen sofa bed and closed in lanai with a dining area. The master bedroom includes a king-size bed and plenty of closet space. Casa Mar's community amenities include 2 sparkling swimming pools, a tennis/pickleball court, beach volleyball, 4 picnic areas with gas BBQs, and 4 shuffleboard courts. Don't miss this opportunity to enjoy all that Siesta Key has to offer from the comfort of this beautiful beach condo!brbrBedroom- KingbrLiving room- Queen Sleeper Sofa and Twin Trundle BedbrbrAdded 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: 23 br*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: $500

Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(9)

$287.54

Wow, it doesn't get any better than this. Stay the month or two on Siesta Key in Florida. Come home to this true beach condo with white Florida decor, ground floor location RIGHT across from the famous newly remodeled Siesta Key Pavilion! The beach is a short walk away. Siesta Key Beach, with its soft quartz sand and turquoise, was voted #1 Beach in the USA and #5 in the WORLD by TripAdvisor 2017. You can't get much closer than this prime location condo - 2 King Bedrooms, both with en-suite baths. Tiled floors, ground floor with dedicated parking space and guest parking. Walk to Siesta Key Village.

Ground-Floor Monthly Condo Facing Siesta Key Beach!

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(44)

$432.76

brSteps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beach, pool & gardens, central AC, and a heated lagoon-style pool for dreamy evening swims. brbrComplimentary Wi-Fi, beach chairs & parking for 1 car make this the ultimate couples’ escape.

❤️ Lovebirds' Retreat - Steps to Siesta Key Public Beach -

Siesta Key, Florida, United States

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Bath

Sleeps

$412.66

Welcome to one of the most beautifully renovated and professionally decorated condominiums on Siesta Key. This stunning two-bedroom, two-bath residence offers more than 1,200 square feet of upscale coastal living and delivers the perfect blend of luxury, comfort, and relaxation.brbrThoughtfully designed with elegant finishes and high-end furnishings throughout, this immaculate condo features a bright, open layout with sophisticated coastal décor and a true resort-style atmosphere. From the moment you walk in, you’ll feel right at home in paradise.brbrThe spacious living area opens to a private screened lanai, the perfect place to enjoy Gulf breezes, morning coffee, or spectacular sunset views. The fully equipped kitchen features modern appliances, quality cabinetry, and everything needed for dining and entertaining with ease.brbrThe primary suite offers a luxurious king bed, serene coastal styling, and a beautifully updated en-suite bathroom. The guest bedroom features two queen beds, ideal for children, friends, or additional guests, along with easy access to the second full bathroom.brbrAdditional amenities include high-speed Wi-Fi, flat-screen televisions, and premium furnishings throughout the residence.brbrLocated just steps from the world-famous white quartz sands of Siesta Key Beach, this exceptional condo places you in the heart of paradise. Guests enjoy resort-style amenities including a heated Gulf-front pool, fitness center, BBQ grilling area, and beautifully maintained tropical grounds. Nearby restaurants, boutique shopping, and the free village trolley make exploring Siesta Key effortless and enjoyable.brbrWhether you’re planning a relaxing beachfront getaway or a memorable family vacation, this exceptional residence offers the very best of luxury coastal living.brbrReserve your dates early—this is one of our most sought-after vacation homes.

Stunning 2BR 2 BA Gulf Views Luxury

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(9)

$1467.77

Escape to unparalleled luxury at this brand-new, exquisitely built vacation rental, completed in June 2025, and ideally situated just steps from the vibrant Siesta Key Village. This magnificent retreat boasts 6 spacious bedrooms, each with its own en-suite bathroom, plus an additional half-bath for ultimate convenience, comfortably accommodating large families or groups. Experience effortless living with a private elevator servicing all levels. The heart of the home is a state-of-the-art gourmet kitchen, fully equipped with top-of-the-line appliances and ample counter space, perfect for culinary enthusiasts. Indulge in the ultimate outdoor oasis featuring an expansive, heated pool and a luxurious hot tub, surrounded by extensive outdoor living areas designed for relaxation and entertainment. A dedicated outdoor kitchen allows for seamless al fresco dining. Ascend to the spectacular rooftop deck for breathtaking panoramic views, ideal for savoring Siesta Key`s famous sunsets. This premier vacation home comes fully stocked with essential beach equipment, ensuring you`re ready for days on the world-renowned Siesta Beach, just a short stroll away. With its impeccable design, unparalleled amenities, and prime location close to Siesta Key Village`s dining, shopping, and entertainment, this newly constructed masterpiece promises an unforgettable, luxurious escape to paradise.

Luxury 6 Bedroom near the Village

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(60)

$378.0

Newly renovated and Decorated Penthouse with ocean views. This 5th floor unit is located Two blocks from the famous MTV “Siesta Key” Crescent Beach and 4 blocks from the #1 beach in the country Siesta Key Beach. If walking is not your thing you can take the free trolley anywhere on the Island. The master has a new King size bed and its own bath that was just redone with beautiful tile and granite work. The second Bedroom has a new Queen and single bed also with its own freshly redone bathroom. There is also a roll out bed if needed. The open kitchen with breakfast bar has granite tops and new stainless steel appliances all that one would need. The New Washer and Dryer are located in the kitchen area. Living room and Dining room combination were just refurnished and has a very comfortable feel to it. You can sit outside on the Lanai for your morning coffee or evening cocktails. You can also gain access to the storage closet that has the items needed for the beach. There are new smart Televisions in both bedrooms and a new 65 inch smart TV in the living room. Wi-Fi, covered parking, elevator and luggage cart all to make for an easier stay. Bay Oaks is located on the bay across the street from the beach. It has its own fishing pier, or a place to sit out and just watch the boats go by. It has BBQ area, picnic tables, Tennis courts, heated pool, club house with pool table and park like grounds. Just down the road you will find boat, jet ski, and bicycle rentals, Excellent restaurants, stores and entertainment in Siesta key Village.

Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(1)

$325.87

Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the island of Siesta Key off Sarasota, Florida, this vacation home has the best of both worlds - the beach in front and boat docks with access to the Intracoastal Waterway in back. Fisherman's Cove is practically surrounded by water!brbrThis unit is on the ground floor and you can walk right out the lanai onto the sand!! Flooring has been upgraded with modern plank tile throughout. The renovated kitchen has granite counter tops and modern appliances including refrigerator, glass top range/oven, dishwasher and microwave. The kitchen is fully equipped including a range of small appliances and Kuerig coffeemaker. The dining area has seating for six (including two bar stools) and is right off the kitchen. The living room has a new extra thick mattress in the queen sleeper, large flat panel HDTV and an amazing view out to the lanai and the Gulf. The air-conditioned lanai has sliders looking out to the Gulf of Mexico and the beach. This unit also has glass sliders between the living room and Lanai giving the option of closing it off so the inside is air-conditioned but sliders can be opened on the Lanai. It is furnished with chairs and table to let you get comfortable as close to the water as possible.brbrSleep at night with the ocean surf right outside your window! The master bedroom has a bay window overlooking the Gulf and beach below. It has a king-size bed, large HDTV, walk-in closet, and en suite bathroom with a tiled tub/shower combo.brbrThis unit has its own dedicated high-speed broadband WiFi. Coin-operated laundry washer/dryers are only steps down the walkway. Boat docks are available for guest use at no extra charge!! Bring your boat or rent one after you get here. Keep it right at the condo all week long. (Note; trailers cannot be stored on site)brbrFisherman's Cove is located less than 25 minutes from Sarasota airport, 90 minutes from Tampa, and two and a half hours from Orlando. Tons of great restaurants and golf courses are nearby.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal brPrimary Bedroom: King bed, private en-suite bath brLiving Room; Sleeper Sofa

Wake Up to the Gulf – Beachfront Living

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Exceptional(4)

$506.42

Step into tranquility at this charming private home, nestled in the heart of Siesta Key. Just a short walk from the famous powder-soft sands of Siesta Beach, this home offers the perfect blend of convenience and relaxation. Featuring a private kitchen, living room, and an onsite private pool, this cottage is perfect for winding down after a day in the popular Siesta Key Village or soaking in that Florida sun!brbrThe Space:brMaster Bedroom: KingbrBedroom 2: QueenbrBedroom 3: 2 Twin bunk bedsbrOffice Area: Twin day bed trundlebrLiving Room, Kitchen, Dining Area, Porch, Patio, Laundry, and Private Pool. brbrThe Location: br- Less than 500 Feet to entrance of Public Beach Access #8 and 9br- 0.4 Miles to Siesta Key Villagebr- 2.3 Miles to Crescent Villagebr- 0.4 Miles to Pool Access br- Less than 500 Feet to local free trolley stop.brSiesta Key has 13 beach access points and a free trolley system making all of Siesta Key easily accessible no matter where you are on the island!brbrImportant things to note:br- Check-in is located at our office. Address will be shared with check-in instructions.br- We only guarantee 1 parking space per rental unit.br- Security Authorization Hold taken upon check-in: $1,000. This hold is released upon inspection of unit after check-out and no damages have been found to the unit. In the event of damages or missing items, the security deposit will be charged by the value of the item, up to but not limited by the full authorized amount.br- To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older and be present for the entire duration of the stay.brbrAdded Amenities Included in Your Stay:br- Free Wifibr- Beach Chairs, Beach Towels, Beach Wagon, and Beach Cooler,br- Partner Property Pool/Hot tub Access,br- Complimentary Bicycles Rentals located at Partner Property,br- 7-days a week, Beachside Management office is open for your convenience and guest needs with after-hours support!

Private Home w/ Pool On Siesta Key!

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(65)

$477.24

Our spacious 2/2 unit is located on the beachside of Siesta Key. No need to cross the road to get to the beach - we have a private, guest-only gate entry right next to our building that leads directly to the beautiful Crescent Private Beach, just about 120 yards away. There are lounges and chairs available right off the path for you to enjoy. We also offer a temperature-controlled community pool for your enjoyment. We are located approximately 1 mile from Siesta Key Village, where you can enjoy dining and shopping.br*As of May 4th we will offer streaming only on our TV's. Please bring your sign-in's.

Siesta Key, Private Crescent Beach 2/2 Getaway

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(53)

$371.78

Located just north of the Stickney Point bridge, this beautiful 2 bedroom, 2 bath condo just steps from Siesta Key Beach! Located on ground level, this unit also puts you steps away from the pool! This unit is comes with 1 king bed and 1 queen bed, plus a full kitchen with refrigerator & dishwasher. Television with basic cable, wireless internet, and a private washer and dryer.

Siesta Key - Midnight Cove #211

Siesta Key, Florida, United States

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Bath

Sleeps

$427.14

Brand new pool !brbrOur place on the #1 Siesta Key beach is near Siesta Key village, quiet turtle beach, downtown Sarasota, Lido Key, St Armand s circle and LongBoat Key. You’ll love our place because of the location, and the ambiance. The best feature - few steps to private Crescent beach (no hike across busy streets to get to the beautiful crystal sands!) brThe building is on a quiet street with no through traffic making it a pleasure to roam safely. brbrOur unit was not at all damaged by the 2 major hurricanes in 2024. Renovations to other units are wrapping up. brbrHappy to answer any questions any time!!

Stylish Retreat on Private Crescent Beach

Siesta Key, Florida, United States

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Bath

Sleeps

Exceptional(4)

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