5+ Bedroom Vacation Rentals In Siesta Key, FL

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Home Steps from Siesta Key Beach and Village with Waterslide! On The Rocks

Siesta Key, Florida, United States

On The Rocks by Siesta Key Luxury Rental Properties brbrSiesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key!br brWelcome to On The Rocks, your luxury vacation haven! This spectacular five-bedroom, five-bathroom retreat is just minutes from the world renowned Siesta Key Beach and a short block from the vibrant Siesta Key Village, offering an abundance of restaurants, bars, and shops. With incredible amenities including a private pool with a waterslide, a putting green, and an inviting private balcony, your unforgettable Siesta Key experience awaits! br brHighlights br• Less than a 5-minute walk to Siesta beach br• 5 Bedrooms / 5 Bathrooms br• 4 Kings, 1 Full/Full Bunk with Twin Trundle, Queen sleeper sofa br• Private pool with waterslide, waterfall and in-ground spa br• Putting green and ping pong table br• BBQ grill br• Beach chairs and towels br• Pet friendly with host approval and pet fee br• Short walk to Siesta Key Village restaurants and boutiques br• Washer and dryer br• 5 Parking spaces br brAt On The Rocks, enjoy a luxurious backyard oasis where you can sunbathe by the premier pool with a sunshelf, slide down the waterslide, or unwind in the spa. For family friendly games, step over to the backyard with a putting green or ping pong table. The covered patio serves as the perfect spot to relax, complete with a cozy seating area, a TV, a BBQ grill, and an outdoor dining table for breezy meals after a day of fun. br brStep into the vibrant living area adorned with dynamic shades of blue and beach inspired decor, instantly immersing you in the coastal atmosphere. The fully equipped kitchen boasts stainless steel appliances, custom cabinetry with ample storage, and a gorgeous dining table that comfortably seats all your guests. Adjacent to the seating area, with a sofa, side chairs, and TV, lies the deck overlooking the pool area, providing another fantastic space to gather. br brRetreat to the luxurious primary bedroom on the second floor, featuring bright decor, access to the inviting upstairs deck, and an elegant ensuite bathroom with a walk-in shower. There are three additional guest rooms, each equipped with a plush king bed and their own ensuite bathrooms, also featuring walk-in showers. The whimsical fifth bedroom delights children with its Sea Life artwork and is outfitted with a bunk bed and a TV, perfect for sleepovers. There is also a conveniently located hall bathroom featuring a shower and tub combination, along with a laundry room that includes a washer and dryer for your convenience. The living room boasts a queen sleeper sofa for additional sleeping arrangements. brbrRoom Details br• Primary Bedroom (2nd floor): King bed, balcony access, ensuite bathroom with walk-in shower br• Second Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower br• Third Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower br• Fourth Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower br• Fifth Bedroom (2nd floor): Full over full bunk bed with twin trundle br• Bonus (Living Room): Queen sleeper sofa br brThis home ensures comfort and convenience with a laundry room equipped with a washer and dryer, allowing you to pack light and enjoy extended stays. br brPlan your dream escape to On The Rocks and experience the best of Siesta Key living! With its luxurious accommodations, prime location, and an array of fun amenities, this vacation rental promises to make your stay memorable. Don’t miss out on an unforgettable experience with Siesta Key Luxury Rental Properties, reserve your getaway today!br brbr- brThis property is managed by Siesta Key Luxury Rental Properties. brbrThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We 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. 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.

Bed

Bath

Sleeps

Exceptional(53)

$1436.08

/ Nightly

Private Vacation Home

Huge Yard with Heated Pool, Steps to Beach - The Pool House

Siesta Key, Florida, United States

The Pool House by Siesta Key Luxury Rental Properties brbrThe Pool House by Siesta Key Luxury Rental Properties is a refined five bedroom, four bath vacation home designed for families and friends seeking effortless coastal living near the beach and village. Located in the desirable Sunset Pointe neighborhood, this Siesta Key luxury rental is just a three-minute walk to Sunset Beach and a short stroll to Siesta Key Village restaurants and shops. With a private heated pool and spa, stylish outdoor living spaces, and airy coastal interiors, this home delivers the perfect balance of relaxation and island fun. brbrHighlights br• 3-minute walk to Sunset Beach br• 5-minute walk to Siesta Key Village dining and shopping br• 5 Bedrooms / 4 Bathrooms br• 4 King beds, 1 Twin over Full bunk bed with Twin trundle, 2 Queen sleeper sofas br• Private heated pool with spa br• Outdoor dining and seating area with TV br• Poolside loungers and BBQ grill br• Beach chairs and beach wagon br• Dog friendly with host approval br• Washer and dryer brbrStep outside to a private tropical oasis designed for year round enjoyment. The sparkling pool and spa are surrounded by comfortable loungers, creating a resort style setting perfect for sunny afternoons or relaxed evenings. The covered outdoor seating and dining area with TV and BBQ grill invites guests to gather for meals, movie nights, or post beach relaxation. brbrInside, The Pool House features an open concept layout with upscale coastal decor and a bright, airy feel throughout. The living area offers plush seating and a welcoming space for movie nights or downtime after a day at the beach. The chef’s kitchen is fully equipped with stainless steel appliances, generous counter space, and a large island with seating, making it ideal for preparing meals together. Next, it's a formal dining area featuring a spacious wood dining table with woven coastal-style seating and warm pendant lighting, creating a relaxed and inviting setting for memorable group dinners. brbrThe home offers a thoughtful bedroom layout that works well for multifamily stays. On the first floor, three primary bedrooms each feature king beds, with select rooms offering ensuite bathrooms with walk-in showers for added privacy and convenience. Upstairs, two additional bedrooms create a flexible retreat with a loft-style feel. One bedroom features a twin over full bunk bed with a twin trundle, perfect for younger guests, while the other offers a king bed and access to a furnished private balcony. These bedrooms share a full bathroom with a walk-in shower. brbrRoom Details br• First Bedroom (1st Floor): King bed, ensuite bathroom with walk-in shower br• Second Bedroom (1st Floor): King bed, ensuite bathroom with walk-in shower br• Third Bedroom (1st Floor): King bed br• Fourth Bedroom (2nd Floor): Twin over Full bunk bed with Twin trundle br• Fifth Bedroom (2nd Floor): King bed, furnished balcony br• Living Area: Two Queen sleeper sofas brbrThe Pool House is ideally situated on Avenida Messina, placing guests just a few homes from the shoreline and within easy walking distance of Siesta Key Village. This Siesta Key vacation home includes an in home washer and dryer, beach chairs and a wagon for easy beach days, and a private pool area perfect for relaxing when not exploring the island. With host approval prior to arrival, dogs are welcome, making this a pet-friendly option for guests traveling with furry companions. brbrCombining a prime Sunset Pointe location, private poolside living, and spacious coastal interiors, The Pool House by Siesta Key Luxury Rental Properties is an ideal choice for families and groups looking to experience the best of Siesta Key. From beach walks at sunset to poolside afternoons and village dining just steps away, this home sets the stage for an unforgettable island escape. Book your stay at The Pool House today and experience luxury coastal living on Siesta Key! brbr- br*Please note- the fireplace is not a working fireplace and is for decorative purposes only. brbrThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment and gate. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We 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. 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.

Bed

Bath

Sleeps

Exceptional(83)

$1467.61

/ Nightly

Private Vacation Home

Heated Pool/Spa w/ Waterslide. Rooftop Deck w/ Gulf Views. Water/Dock Access

Siesta Key, Florida, United States

Aloft on Canal by Siesta Key Luxury Rental Properties brbrWelcome to Aloft on Canal, an upscale eight bedroom, six and a half bath Siesta Key luxury rental designed for effortless coastal living and memorable group getaways. Located just a four-minute walk to Siesta Key Beach and directly across from the canal with dock access, this refined beach house blends island-inspired interiors with resort style outdoor living. With a private heated pool and spa, waterslide, rooftop deck, elevator, and generous parking, this home is ideal for large families, multifamily groups, and extended stays near Siesta Key Village and local favorites along Midnight Pass Road. brbrHighlights br- 4-minute walk to Siesta Key Beach br- 8 bedrooms and 6.5 bathrooms br- 6 king beds, 1 full bed, 6 twin beds br- Private heated pool with waterslide and spa br- Canal and dock access across the street br- Rooftop deck and multiple balconies br- Elevator access to all levels br- Game room with ping pong table br- Dog friendly with approval br- 4 parking spaces brbrStep outside to your tropical outdoor oasis, where a private heated pool takes center stage with a rock waterslide, sun shelf, and inviting spa. The backyard is designed for relaxed island days and lively evenings, complete with outdoor seating and a BBQ grill for casual meals after the beach. Canal access across the street opens the door to kayaking, paddleboarding, and boating adventures, adding a waterfront element that elevates this Siesta Key vacation home with pool. The rooftop deck offers a peaceful retreat above it all, perfect for sunset moments after a day spent enjoying the Gulf Coast. brbrInside, this home showcases modern coastal decor and a bright, open concept layout ideal for gathering. The living area features ample seating and a large TV, creating a comfortable space for movie nights or downtime between beach outings. Sliding glass doors bring natural light and connect seamlessly to outdoor living areas. The gourmet kitchen is fully equipped with high end appliances and two large islands, making it easy for multiple cooks to prepare meals together. Whether hosting family dinners or casual breakfasts before heading to the beach, this kitchen supports effortless entertainment. brbrThe primary suite on the third floor offers a king bed, private balcony, and a spa inspired ensuite bathroom with a walk-in shower and a soaking tub, creating a serene retreat. Additional bedrooms feature king beds with ensuite or shared bathrooms, many with balcony access, maintaining a refined and restful atmosphere throughout. The home also includes bunk accommodations designed with younger guests in mind, offering flexibility without sacrificing comfort. Bathrooms are thoughtfully appointed with walk-in showers and polished finishes, ensuring convenience for larger groups. brbrRoom Details br- Primary Bedroom (Third Floor): King bed, private balcony, ensuite bathroom with walk-in shower and stand-alone tub br- Second Bedroom (Third Floor): King bed, balcony access, ensuite bathroom with walk-in shower br- Third Bedroom, Third Floor): King bed, ensuite bathroom with walk-in shower, connects to fourth bedroom br- Fourth Bedroom (Third Floor): Twin over full bunk bed with twin trundle br- Fifth Bedroom (Second Floor): King bed, balcony access, ensuite bathroom with walk-in shower br- Sixth Bedroom (Second Floor): King bed, balcony access, jack-and-jill bathroom with walk-in shower br- Seventh Bedroom (Second Floor): King bed, jack and jill bathroom with walk-in shower br- Eighth Bedroom: Two twin bunk beds brbrThis home participates in our Professional Linen Program, providing hotel quality linens and towels that are freshly laundered for every stay. Dog-friendly accommodations are available with prior approval and an additional fee. Guests will enjoy being close to Siesta Key Village, with shops and restaurants for a one of kind entrainment. With easy access to attractions and the Gulf, this location offers both relaxation and adventure. brbrFrom its private pool and canal access to its spacious layout and walk-to-beach location, Aloft on Canal by Siesta Key Luxury Rental Properties delivers coastal comfort with elevated style. Book your stay today and experience the best of Siesta Key luxury rentals for your next beach getaway! brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis property participates in our Professional Linen Program. This ensures high quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrIf you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry, and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon.

Bed

Bath

Sleeps

Exceptional(80)

$1258.02

/ Nightly

Private Vacation Home

Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

Siesta Key, Florida, United States

Sea Spray by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sea Spray! This eight-bedroom and six-and-a-half-bathroom home will check off all the boxes for your desired Siesta Key rental. It is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area. So, catch some sunshine at the beach or enjoy great live music, dining, or shopping in the village. brbrHighlightsbr• Private Dock br• Rooftop Deckbr• Beach Viewsbr• Less than a 5-minute walk to the beachbr• Private Pool with Waterslide and In-ground Spabr• Ping Pongbr• Foosball tablebr• Convenient location near dining and shoppingbr• Dog friendly with approval and additional feebrbrThe spectacular backyard is built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. You’ll love the lounge chairs, dining options, and BBQ grill. brbrJust across the street is your own private dock on the canal So, throw in a line and try your luck at fishing, or explore the bay by boat, kayaks, or paddleboards! brbrTake the elevator up to the main living floor, where you’ll find a lovely living area with plenty of seating for all your guests and large sliding doors leading to the furnished balcony; this is where you can access the rooftop deck. The kitchen highlights stainless steel appliances, cookware essentials, and two island seating options; the dining table and nook seating are adjacent, great for large parties. brbrThe game room is located just off the pool area with a ping pong table, a foosball table, and a refrigerator. brbrThe primary bedroom is a dream! It’s spacious with a walk-in closet, a private balcony with Adirondack chairs, an ensuite bathroom with a delightful baby blue double vanity, a large walk-in shower, and a premium standalone tub. The second/third bedroom has a unique setup with a King bed and a bunk bed with a curtain to separate the two, an ensuite bathroom with a walk-in shower, making it a perfect room for parents and kids! There are two King bedrooms with ensuite bathrooms and two King bedrooms that share a Jack-n-Jill bathroom with a walk-in shower. The last bedroom is the bunk room with easy access to the hall bath with a walk-in shower. The living room has a sleeper sofa and a laundry room on the second floor. brbrRoom Details br-Primary Bedroom, 3rd floor: King bed, private balcony, and ensuite bathroom with walk-in shower and standalone tub br-Second Bedroom, 3rd floor: King bed and shared ensuite bathroom with the third bedroom br-Third Bedroom, 3rd floor: Twin over Full Bunk Bed with a Twin Pull Out Trundle and shared ensuite bathroom with the second bedroom br-Fourth Bedroom, 3rd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower br-Fifth Bedroom, 2nd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower br-Sixth Bedroom, 2nd floor: King bed, balcony access, and Jack-n-Jill bathroom with walk-in shower br-Seventh Bedroom, 2nd floor: King bed and Jack-n-Jill bathroom with walk-in shower br-Eighth Bedroom, 2nd floor: Two Twin bunk beds and ensuite bathroom with walk-in shower brbrBook your dream vacation today! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 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. brbrThis home is managed by Siesta Key Luxury Rental Properties. We 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. 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.

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Exceptional(80)

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Luxe Lagoon | Located in SK Village! Private Pool & Spa, Rooftop, Pet Friendly ?️☀️?

Siesta Key, Florida, United States

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Siesta Key Luxe w/ Pool, Rooftop & Steps to Beach

Siesta Key, Florida, United States

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Steps to Beach/Siesta Village-Resort Pool w/Slide

Siesta Key, Florida, United States

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Exceptional(80)

$3229.57

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Entire Resort on Heron Lagoon, the Siesta Key Bungalows

Siesta Key, Florida, United States

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Sunset Gazers Paradise - Resort Pool - Mini Golf

Siesta Key, Florida, United States

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Beachfront Luxury - Resort Pool - Steps to Village

Siesta Key, Florida, United States

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Bath

Sleeps

5+ Bedroom Vacation Rentals In Siesta Key, FL

$1436.08

$1467.61

$1258.02

Rent a place that suits your needs

Most popular vacation rentals in Siesta Key

$2522.03

$2135.02

$2157.13

$2193.20

$2342.88

$2445.50

$2479.18

$3229.57

$3133.33

$3110.58

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