Vacation Rentals By Owner In Siesta Key, FL

We're right on the beach! High-rise View, 11th floor.brLuxury condo, Crystal Sands on Midnight Pass Rd., is one of the most popular condos on Siesta Key's Crescent Beach, ranked as one of the whitest and most powdery sands in the world, as judged by the br'Great International White Sand Beach Challenge.'brOcean views from all rooms. Master bedroom with master bath has king size bed and access to lanai. Guest bedroom has queen size bed and access to lanai.

Oceanfront, Views 11th flr, On the beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$944.49

Bimini Breeze by Siesta Key Luxury Rental Properties brbrWelcome to Bimini Breeze, a fully remodeled 2-bedroom, 2-bath ground floor home in the heart of Siesta Key, less than a block away from Siesta Key Village and Siesta Key Beach! This vacation rental has a resort style pool that is inviting and perfect for relaxing while enjoying the warm sun. Walk less than five minutes to the shimmery white sands of the best Gulf beach on Siesta Key or Siesta Key Village for dining and shopping. This Siesta Key vacation rental is ideal for couples, small families, or friends seeking easy beach access and island nightlife. brbrHighlights br• 4-minute walk to Siesta Key Beach br• 2 Bedroom / 2 Bathroom br• 1 King, 1 Full/full bunk, 1 Queen sleeper sofa – sleeps 8 br• Private resort style pool with sun shelves br• 3-minute walk to Siesta Key Village shops and dining br• Dog friendly with host approval br• Beach chairs and beach towels included br• Professional linen programbr• Private backyard seating and outdoor dining for six br• 3 Parking spaces brbrEnjoy your private pool with generous space and sun shelves for lounging, while the provided beach gear allows for easy days on the sand. Relax outside and enjoy the warm Florida sunshine or explore delicious local dining and shopping with Siesta Key Village nearby. brbrThe bright open living room includes blue hues, comfortable seating, and large TV opens through sliding glass doors to the backyard and pool. Fully equipped kitchen stainless steel appliances, large island seating for four, and coastal decor makes meal prep effortless. Dining and living areas designed for relaxed island living. brbrThe primary bedroom features a king bed, TV, ample closet space, and an ensuite with a walk-in shower. The second bedroom offers a full over full bunk ideal for kids or extra guests with access to the hall bathroom providing a shower/tub combination. The queen sleeper sofa in the living room provides additional sleeping space. brbrRoom Details br• Primary Bedroom: King with ensuite bathroom with walk-in shower br• Second Bedroom: Full over full bunk bed br• Living room: Queen sleeper sofa brbrA washer and dryer are provided in the house. Bike rentals or the free island trolley will help you explore the key. Siesta Key Village is steps from your doorstep, with local shops, cafes, restaurants, and nightclubs for live music and drinks. Whatever your vacation speed is, this home makes island living a breeze. brbrBook now and experience an effortless island living at Bimini Breeze by Siesta Key Luxury Rental Properties, walk to the beach and Siesta Key Village, relax by your private pool, and enjoy coastal comforts. Reserve your dates today! br 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 has an active Ring doorbell and additional video surveillance on the pool equipment only. 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. brbr3 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. 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.

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1436.08

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.

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1467.61

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.

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$655.74

Aruba by Siesta Key Luxury Rental Properties brbrWelcome to Aruba! A fully refreshed 3-bedroom, 2.5-bath home located in the heart of Siesta key, just a short 4-minute stroll from Siesta Key Beach and within easy walking distance of Siesta Key Village! Walk less than five minutes to the shimmery white sands of the best Gulf beach on Siesta Key or Siesta Key Village for dining and shopping. With a beautifully large, private pool, BBQ grill, and dog friendly accommodations, Aruba is ideal for families or friends who want effortless beach days and relaxed island entertainment. brbrHighlights br• 4-minute walk to Siesta Key Beach br• 3 Bedroom / 3 Bathroom br• 2 Kings, 1 twin/twin bunk with twin trundle, 1 queen sleeper sofabr• Short walk to Siesta Key Village shops and restaurants br• Private pool with covered outdoor dining area br• BBQ grill br• Dog friendly (with approval and fee) br• Washer and dryer on site br• 3 parking spaces br• Near free island trolley brbrPrivate backyard pool for swimming and lounging, including a covered patio with table and grill for alfresco meals and entertaining. With a dog friendly policy, enjoy the tropical atmosphere with your furry friends. Stroll to the beach and bring the provided beach chairs or head to Siesta Key Village and explore the nearby attractions. brbrThe bright living area offers multiple sofas, side chairs, a TV, and a bar top for casual snacks and games. The fully equipped kitchen features stainless steel appliances, plenty of cabinets, and an adjacent dining room with pool views, perfect for group meals and easy flow to the outdoor space. brbrThe primary bedroom includes a king bed, premium mattress, TV, and ample storage. The second bedroom also has a king bed, premium mattress, and TV. The third bedroom is a nautical themed bunk room with two twin over twin bunks plus a twin trundle and an ensuite with a walk-in shower, ideal for children. The hall bath includes shower/tub combination, easily accessible from both the primary and second bedrooms. The living room queen sleeper sofa adds extra sleeping space, with access to the hall bath and half bath which includes a washer and dryer. brbrRoom Details br• Primary Bedroom: King bed br• Second Bedroom: King bed br• Third Bedroom: Twin-over-twin bunk with twin trundle, ensuite bathroom with walk-in shower br• Living room: Queen sleeper sofa brbrThis home includes a washer and dryer, hair dryer, iron and ironing board, as well as 3 parking spaces. Walk to beach activities like snorkeling, paddleboarding, and kayaking. Stroll to Siesta Key Village for shopping, dining, and nightlife, or hop the free trolley or rent a golf cart. brbrBook Aruba by Siesta Key Luxury Rental Properties for a private pool Siesta Key vacation, sunny beach days, easy access to Siesta Key Village, and comfortable coastal living await. Reserve your dates today.br 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 has active video surveillance on the pool equipment only. brbr3 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 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. 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.

Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1209.13

Casa De Siesta | Private Heated Pool + Walk to Siesta Key Villagebrbr Why You'll Love This HomebrStep into tropical elegance just steps from the village. You'll enjoy sunlit interiors, a private heated pool & hot tub, and seamless indoor‑outdoor living designed for connection and rejuvenation.brbr ‍ ‍ Perfect ForbrFamily groups, multi‑gen travel, or couples seeking privacy with shared amenities.brbr ️ Imagine ThisbrWake up to golden light filtering through palms, hit the pool for a morning dip, then wander down the block to sip coffee at a café in Siesta Key Village. Midday, stretch out on the sand at Siesta Key Beach (a quick 0.3 mile stroll), then return for a BBQ by the pool. As evening falls, gather with friends in the hot tub, and enjoy the sunset. You'll feel relaxed, refreshed, and like you're exactly where you want to be.brbr Where You'll SleepbrVilla Fiesta:br• Bedroom 1: King Bed, Ensuite Full Bath, First Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, First Floor, TVbr• Living Room: Queen Sleeper SofabrbrVilla Margarita:br• Bedroom 3: King Bed, Ensuite Full Bath, Second Floor, TVbr• Bedroom 4: Queen Bed, Shared Bath, Second Floor, TVbr• Living Room: Queen Sleeper Sofabrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, Nightlifebrbr⌛ Don't wait—this home books quickly. Your reservation includes peace of mind with our CottageClean™ program: a 6‑hour deep clean and 35‑point inspection so you arrive to perfection.brbr Need to Know - This home is a combination of 2 units - Villa Fiesta - 312R and Villa Margarita - 314L that are accessed by different entrances and do not share common space indoors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pups stay just as wonderful as yours.

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$611.32

Villa Fiesta | Pet Friendly Home In Siesta Village, Shared Heated Pool and Hot Tub, Walk to the Beach!brbr Why You'll Love This HomebrLive like a local in the heart of Siesta Key Village, just a 5-minute walk to the island's world-famous beach. Villa Fiesta blends vibrant charm with relaxed coastal style—complete with a shared heated pool, dog-friendly policy, and the freedom to walk to everything. This colorful island retreat is made for morning strolls, beach days, and sunset BBQs.brbr ‍ ‍ Perfect ForbrSmall families, couples, or friend groups looking for a lively, walkable Siesta Key experience—plus one well-behaved pup (under 25 lbs) is welcome too!brbr ️ Imagine ThisbrThe village is alive with energy as you arrive—bike bells, café chatter, and the scent of coconut sunscreen in the air. You step inside Villa Fiesta and instantly feel at ease. The coastal-inspired living room invites you to kick off your flip-flops and stretch out on the sofa. Upstairs, sun-drenched bedrooms await, each designed for rest and recharge. After a lazy afternoon on Siesta Key's powder-white beach—just 0.3 miles away—you return to the shared backyard oasis. The grill sizzles, the hot tub bubbles, and laughter echoes as the sun dips below the palms. Every moment here feels light, bright, and unforgettable.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Full Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Full Bath, Third Floor, TVbr• Living Room: Queen Sleeper Sofa – Main Living Area, Half Bath Nearbybrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Fiesta places you in the perfect spot to enjoy it all.brbr⌛ Don't wait—Homes this close to Siesta Key Village go fast—lock in your stay now. Your reservation includes full access to our CottageClean™ program: a 6-hour deep clean and 35-point inspection that ensures a pristine, worry-free arrival.brbr NEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This home has stairs, if you or someone in your party has trouble with stairs, please contact us for more details. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours.

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$209.05

Number 201, with recent updates, is a beautifully situated spot to enjoy the comforts of home, while you are away from home! 2 spacious bedrooms, one master with a king sized bed, and another with 2 full/queen beds. Additionally, there are 2 full bathrooms. A fully stocked kitchen, with all new appliances and everything that is needed to prepare your own meals is also included. There is a screened in Lanai as well. Wifi and cable (3 TV's), as well as laundry. There are 2 large swimming pools, 2 whirpool spas, shuffleboard, 2 lighted tennis courts and 2 pickle ball courts. This location is 2.5 hrs to Disney World in Orlando and 1 hour to Busch Gardens in Tampa

Beautiful Siesta Key- Drop your bags and head to the White Sandy Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$593.02

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Palm Island Canal Estate! brbr brbrIndulge in the ultimate Siesta Key lifestyle at this breathtaking Spanish Mediterranean custom estate. Nestled in a prestigious, quiet enclave, this 3,500 sq. ft. masterpiece offers a rare combination of canal-front serenity and beachside convenience. Whether you’re launching a kayak from your private backyard or taking a 5-minute stroll to the powdery sands of Beach Access #10, this home is the pinnacle of coastal luxury. brbr brbrTHE OUTDOOR OASIS brbr- Private Splash Pool: Refresh in your heated pool (maintained at a perfect 86°F year-round at no extra cost). brbr- Canal-Side Living: Launch your kayaks directly from your backyard and explore the scenic waterways of Siesta Key. brbr- Outdoor Lounging: Multiple screened lanais and seating areas offer the perfect vantage point for morning coffee or sunset cocktails. brbr brbrDESIGNER INTERIORS brbr- Mediterranean Elegance: Custom architecture featuring dark cherry cabinetry, granite countertops, and soaring ceilings. brbr- Coastal Sophistication: Professionally decorated with Tommy Bahama-inspired furnishings and a dedicated wet bar for evening entertaining. brbr- Dining for the Whole Group: Features a formal dining room, a side café nook, and a convenient main-floor powder room for guests. brbr brbrHOME LAYOUT & BEDROOMS brbr- Suite Privacy: The 4-bedroom layout is spread across multiple levels, offering maximum privacy for large groups. brbr- Master Sanctuary (Upper Level): A King suite with private lanai access and a spa-like ensuite featuring a jetted tub and walk-in shower. brbr- King Guest Suite (Mid-Level): A spacious King room with a private ensuite bathroom. brbr- Additional Guest Rooms (Upper Level): One Queen bedroom with balcony access and one Twin bedroom - perfect for kids or extra guests. brbr- Remote Work Den: A dedicated workspace with a desk for those who need to stay connected. brbr brbrPROPERTY FEATURES brbr- Climate & Comfort: Central AC and ceiling fans throughout. brbr- Tech-Ready: Dedicated high-speed WiFi and YouTube TV included. brbr- Parking & Extras: Spacious garage/driveway parking and complimentary beach gear provided. brbr brbrIMPORTANT INFO brbr- Layout Note: This custom home features multiple staircases, which adds to the architectural charm but may not be suitable for those with limited mobility. brbr- Pristine Environment: Located in a quiet residential area. Strictly no pets, smoking, or parties. brbr brbrYOUR LUXURY BEACH VACATION STARTS THE MOMENT YOU RESERVE. BOOK PALM ISLAND ESTATE TODAY!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Palm Island Estate: Mediterranean Luxury w/ Pool & Private Canal Access

Siesta Key, Florida, United States

4

Bed

3

Bath

8

Sleeps

$208.11

Welcome to this beautifully remodeled Bayside Mid-rise unit. This spacious 2-bedroom, 2-bathroom condo is situated on the 5th floor, brbrAs you step inside, you'll be greeted by a tastefully decorated living area with modern furnishings and a serene coastal color palette. The open-concept design seamlessly connects the living, dining, and kitchen areas, creating a perfect space for relaxation and entertainment. The living room features comfortable seating, a flat-screen TV, and large sliding doors that lead to a private, enclosed balcony.brbrThe dining area, adjacent to the kitchen, is well-appointed with a stylish dining table that seats four, making it ideal for family meals or entertaining guests. The fully equipped kitchen boasts contemporary appliances, ample counter space, and all the essentials needed to prepare delicious meals.brbrThe master bedroom is a tranquil retreat, complete with a king-size bed, en suite bathroom, and plenty of storage space. The guest bedroom is equally inviting, offering a queen-sized bed and easy access to the second bathroom located in the hallway. brbrAdditional amenities include hardwood floors throughout, a full-size washer and dryer for your convenience, and a covered parking space. Guests will also have access to high-speed internet, beach access, tennis courts, exercise facilities, and two swimming pools.brbrThis unit is perfect for those seeking a luxurious and comfortable stay with all the conveniences of home. Please note that there is a 30-night minimum stay requirement, and pets are not permitted on the property.

1255-501 Bayside Retreat with Coastal Charm

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$559.29

Welcome to your dream getaway on Siesta Key! This beautifully appointed, fully renoavted 3-bedroom, 3-bathroom waterfront home offers the perfect blend of comfort, luxury, and island living. Nestled on a quiet canal just minutes from the world-renowned Siesta Beach, this private retreat is ideal for families, couples, or boating enthusiasts. Pet Friendly - all pets must be approved by management. Pet Fee $250.brbrKey Features:br3 Spacious Bedrooms – Comfortably accommodates families, couples, or small groupsbrPet Friendly - All pets must be approved by management. Pet Fee $250.brPrivate Heated Pool – Soak up the sun or take a refreshing dip any time of yearbrCanal Access with Private Boat Dock – Bring your boat or rent one locally to explore Sarasota Bay and the GulfbrJust Minutes from Siesta Key Beach – Walk, bike, or drive to one of America’s top-rated beaches with powdery white sandbrFully Stocked with Beach Gear – Includes chairs, umbrellas, towels, and coolers for hassle-free beach daysbrGourmet Kitchen – Equipped with everything you need to prepare meals at homebrUnbeatable Siesta Key Location – Close to Siesta Village shops, restaurants, and the vibrant nightlife of downtown SarasotabrModern Comforts Throughout – High-speed Wi-Fi, smart TVs, laundry, and stylish furnishings for a relaxing staybrSpacious Outdoor Entertaining Area – Perfect for grilling, dining al fresco, or lounging by the pool with tropical viewsbrbrWelcome to Siesta Key, a sun-drenched barrier island on Florida’s Gulf Coast, known for its laid-back charm, vibrant beach village, and the world-famous Siesta Beach, consistently ranked among the best in the U.S. thanks to its soft, powdery white quartz sand.brbrWhether you're seeking a relaxing retreat or an adventure-filled escape, Siesta Key offers something for everyone. Spend your days swimming in crystal-clear turquoise waters, paddleboarding along gentle bays, or exploring the lush mangrove tunnels by kayak. In the evening, stroll through the lively Siesta Key Village, where you'll find open-air dining, boutique shopping, and live music under the stars.brbrWith easy access to downtown Sarasota, top-notch golf courses, art galleries, and nature preserves, Siesta Key is the perfect blend of tropical tranquility and cultural sophistication.brbrThis island paradise is a beloved destination for families, couples, and snowbirds alike—and once you visit, you’ll understand why guests return year after year.brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you. brbrGulf Coast Holiday Homes offer a wide range of services including: br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations. br- 'Preferred Vendors' menaing you can trust the company you use for rentals.brbrAll properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrStep inside to discover an open-concept living area filled with natural light, coastal-inspired décor, and all the modern amenities you need. The fully equipped kitchen features quartez countertops, stainless steel appliances, and a breakfast bar, perfect for morning coffee or evening cocktails.brbrEach of the three spacious bedrooms offers a serene escape with plush bedding and en-suite or nearby bathrooms. The master suite includes direct access to the pool deck and a spa-like bathroom with walk-in shower.brbrOutdoors, your own private heated pool awaits, surrounded by tropical landscaping and a sun-soaked patio complete with lounge chairs and a BBQ grill. Just steps away, the private boat dock gives you direct access to the waterway, bring your boat or rent one nearby and explore Sarasota Bay or head out to the Gulf.brbrBeach chairs, towels, and bikes for your conveniencebrbrWhether you're relaxing by the pool, launching off for a day on the water, or strolling the charming shops and restaurants of Siesta Village, this exceptional home is your gateway to the ultimate Florida vacation.brbrProperty can be accessed via electronic door code, sent to allow guests on day of arrival. brbrDirections: Take I-75 South to Exit 205 for FL-72 W toward Sarasota. Continue on FL-72 W, which becomes Stickney Point Rd. Turn right onto Midnight Pass Rd, heading south. Turn left onto Avenida De Paradisio; the destination will be on your left just before the cul-de-sac.brbrParking is available on site for a maximum of 3 cars in the driveway. Parking is available on the street. The garage is not available to guests.brbrThis property must be rented for a minimum of 30 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrAccidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at Gulfcoast Holiday Homes. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71. brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.

Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by Gulf Coast Holiday Homes

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$427.18

Siesta Key boasts a breathtaking beachfront condo. As you step inside, you'll be greeted by a fully stocked kitchen, perfect for whipping up delicious meals. Enjoy your morning coffee on the balcony, taking in the breathtaking views. Spend your days lounging by the outdoor pool or relaxing in the soothing hot tub. Explore the nearby Crescent and Siesta Key Beaches within a few short steps. For a change of pace, take a 20 drive to Lido Beach or St Armand's Circle. Back at the condo, you'll find all the comforts of home, including 3 smart TVs with cable channels, a washer and dryer, and complimentary WiFi. Whether you're seeking a relaxing getaway or an adventure-filled vacation, this beachfront condo has everything you need and more.

Exceptional Beachfront condo on Crescent Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1258.02

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.

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$672.52

Stay in one of Siesta Key’s newest beachfront complexes with breathtaking gulf views and high-end amenities. Perfect for a group of 6! This gated, luxury building with only 26 units offers 2 pools, hot tub, fitness room, lush gardens, and private beach access with lounge chairs.brbrWhat You’ll Love:brbr-Spacious 3-bedroom, 2-bath condo with open layout and tons of natural lightbr-Main balcony (access from living room and master bedroom) with gulf views and two lounge chairsbr-Second balcony (access from both guest bedrooms) with dining table for six and grillbr-Beautiful, fully equipped kitchen with granite countertops, Keurig and drip coffee maker, blender, cookware and morebr-Comfy living room with two couches, leather chair, and large flat-screen TVbrbrSleeping Arrangements:brbr-Master Bedroom: King bed, private balcony access, en-suite with clawfoot tub, walk-in shower and dual vanitybr-Second Bedroom: Two queen beds, SMART TV, private balcony accessbr-Third Bedroom: Twin bunk beds, private balcony accessbr-Guest bathroom with walk-in glass shower and granite vanitybrbrExtras Included:brbr-Dedicated covered parking space for one vehiclebr-Beach chairs, towels and umbrellabr-2 pools, hot tub, fitness room, lush gardens, and private beach access with lounge chairsbrbr7 night min stay. Thank you!

Beautiful Gulf View, Private Beach Access, Fitness Room

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$527.35

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!brbr Why You'll Love This HomebrTucked above the lively village streets, Villa Margarita offers a breezy, light-filled retreat with elevated privacy, designer comfort, and shared access to a heated pool and spa—just 0.3 miles from world-famous Siesta Key Beach.brbr ‍ ‍ Perfect ForbrCouples, small families, or beach lovers craving a stylish escape with village convenience.brbr ️ Imagine ThisbrWake to a soft breeze drifting through upstairs windows. Get the day going by brewing coffee in the bright kitchen, step onto the balcony, and watch the village below slowly wake up. By late morning, you're walking to the beach—cooler packed, flip-flops on. After a sun-soaked afternoon, it's back to the villa to dip into the shared hot tub, grill fresh seafood, and toast to another unforgettable day on the Key.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Second Floor, TVbr• Bonus Room: Queen Sleeper Sofa – Main Living Areabrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Margarita places you in the perfect spot to enjoy it all.brbr⌛ Don't Wait - This sought-after upper unit fills fast—reserve now and travel worry-free with our CottageClean™ program: a 6-hour deep clean followed by a 35-point inspection before every stay.brbr NEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours.

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

2

Bed

1

Bath

6

Sleeps

$399.53