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Siesta Key, Florida

SKLRP - 2 (1)

World-Class Siesta Key Vacation Rentals & Tropical Hotel

Enjoy the ultimate beach getaway to Siesta Key, Florida, with PRIME VACATIONS. Home to turquoise waters, the bustling Siesta Key Village, and one of Florida’s top beaches planning an escape here is truly a trip to paradise. Stay in style by finding your dream Siesta Key vacation rental or boutique hotel room. Start planning your visit by browsing our collection of vacation rentals and hotel rooms in the popular Florida town today.
Showing 12 of 450 properties



Condo

Jamaica Royale 703

Jamaica Royale 703

Unit 703 has a wonderful high view above the action on the beach. Spot porpoises in the Gulf and see all the way to Venice as you enjoy a meal on the glass enclosed balcony. Your 48" TV is available for an evening movie or show. You can also enjoy the three heated pools, one of which is right at the beach edge. This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.

2 2 6
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Condo

Jamaica Royale 004

Jamaica Royale 004

Absolutely stunning unit. Just remodeled and updated with all modern conveniences. Kitchen has most up-to-date appliances. Marble and granite throughout. This unit has speakers throughout the condo with an I-pod docking station that sounds incredible. This unit is located in the garden area close to the beach. You have view of the Gulf while sitting on the full patio which includes lounges, patio table, and chairs. There are three sparkling pools on the property, along with shuffleboard and BBQ. No discounts given per owner. This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.

1 1 4
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Duplex

Summer Salt (SKLRP)

Summer Salt (SKLRP)

Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! What a GREAT LOCATION in SIESTA KEY VILLAGE for this Ground Level Duplex Unit w/ a HEATED POOL! 2 Beds/2Baths Duplex Unit - Sleeps 8. Huge Pool Patio with 2 BBQ's, 2 Outdoor Dining Tables for 4 People, and multiple chaise loungers and Adirondack chairs to use for sunning and relaxing. Walk to Beach, Dining, Shops. This property is walking distance to everything! And, just 2-3 short blocks (less than 5 min walk) to the beach depending on which beach access you choose. There are also free shuttles and a trolley available in case you do not want to walk. What an amazing property at an amazing value! Siesta Key Village is literally in your front yard. This vacation unit is located in the heart of Siesta Key, yet just far enough away that you still have your privacy on your private lanai or shared pool area. The home also has a large pool patio and a shared heated pool. The pool is only shared with the other 2-bedroom unit in this duplex, and there is so much room and seating, plus 2 BBQ Grills and 2 Patio dining options you won't feel crowded at all. If you rent both units, you'll have a 4 Bedroom, 4 Bathroom Home with 2 Kitchens and a Private Heated Pool! The home itself has a spacious great room, with a living, dining, and kitchen space that is joined. The kitchen has stainless steel appliances, solid wood cabinets, and granite countertops. The dining area has a 4 person dining table and 4 more dining spots at the countertop bar for a total of 8 indoor dining seats. The living room has plenty of seating as well, along with HDTV & XBOX, and there is Free WiFi throughout the home and exterior spaces. The 2 bedrooms and 2 bathrooms offer your group or family privacy and the perfect place to take a siesta after a long day at the beach. The Master Bedroom features a King bed and it has an en suite bathroom. The bunk room has a Queen bed and a Full over Full Bunk Bed (sleeps 6 total people in this room) and a bath just outside it's door that doubles as the living space bathroom as well. The private covered patio space has seating for two and there is additional outdoor dining seating on the pool patio for 4 persons. But who wants to be indoors when you're vacationing in Siesta Key Beach! Hang out on the patio or just soak away in the pool as you listen to the sounds of music and fun from Siesta Key Village. When you're rested and ready to enjoy Siesta Key, the beach and the Village are both just a short walk away. Feel free to take a night off from eating out at one of the fantastic restaurants within walking distance and walk across the street to Morton's Market and get some groceries for a home cooked meal or BBQ. If you need more space for your family and friends, feel free to rent the unit upstairs as well and double your occupancy to 16. This will also gain you access to the private pool so you'll have a private heated pool, 2 kitchens, 2 master suites, 2 Bunk rooms, and plenty of space for everyone. Inquire today for information about renting both properties. This 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. This property has active video surveillance on the pool equipment. At A Glance • 2 Bedroom, 2 Bathroom Home - Ground Level Duplex Unit • Heated Pool (Shared), Patio Seating and BBQ Grill • Literally Steps to Siesta Village and 2-3 Blocks to Siesta Beach • Beach Chairs and Beach Towels Included - Inquire for More Details • Sleeps 8 - 1 King Bed and 1 Full over Full Bunk Bed and 1 Queen Bed • Part of our Professional Linen Program • Full Kitchen with Supplies and Private Washer/Dryer • Parking, Free WiFi, and HDTV Included • Property Manager Program - Let us help you Vacation the Right Way

2 2 8
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Townhouse

Our House at the Beach C-106

Our House at the Beach C-106

Lake house offers a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances, including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the grounds. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Lake House offers central A/C, ample closets and storage space, high-speed Internet, cable TV in the living room and each bedroom, and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts. This Lake House unit is right across the street from Siesta Key public beach, making a splash in the ocean or just a walk on the sugar sand beach a just a few steps away.

2 2 6
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Condo

Jamaica Royale 069

Jamaica Royale 069

Enjoy this 2 bedroom 2 bath garden view villa located in the garden/pool #2 area of our beautifully landscaped grounds. For your convenience, the master bathroom shower/tub has grab bars. Swim in any of the 3 heated pools on the property, see who the shuffleboard winner is while barbecuing lunch or dinner at the community patio. This great unit is close to the beach as well and the chairs are all there for your use. We look forward to having you! This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.

2 2 6
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Condo

Gulf and Bay Club- B608

Gulf and Bay Club- B608

A beautifully updated 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy the state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!

2 2 6
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House

Sea Spray

Sea Spray

Sea Spray by Siesta Key Luxury Rental Properties 538 Canal Rd Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Welcome to Sea Spray, a beach and boaters paradise with a private dock across the street and just a block from the famous Siesta Key beach! This eight-bedroom and six-and-a-half-bathroom home boasts a spectacular backyard 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. Pack your bags for the best vacation ever! Take 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. The 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. Room Details -Primary Bedroom, 3rd floor: King bed, private balcony, and ensuite bathroom with walk-in shower and standalone tub -Second Bedroom, 3rd floor: King bed and shared ensuite bathroom with the third bedroom -Third Bedroom, 3rd floor: Twin over Full Bunk Bed with a Twin Pull Out Trundle and shared ensuite bathroom with the second bedroom -Fourth Bedroom, 3rd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower -Fifth Bedroom, 2nd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower -Sixth Bedroom, 2nd floor: King bed, balcony access, and Jack-n-Jill bathroom with walk-in shower -Seventh Bedroom, 2nd floor: King bed and Jack-n-Jill bathroom with walk-in shower -Eighth Bedroom, 2nd floor: Two Twin bunk beds and ensuite bathroom with walk-in shower The Outdoor space has a covered patio with lounge chairs, a dining table, a BBQ grill, a TV, and an incredible pool area! The game room is located just off the pool area with a ping pong table, a foosball table, and a refrigerator. Throw in a line and try your luck at fishing, or explore the bay by boat, kayaks, or paddleboards! This home 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. Book your dream vacation today! - This 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. This 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. 4 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. This 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. Please 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. At A Glance • Private Dock • Rooftop Deck • Beach Views • Less than a 5-minute walk to the beach • Private Pool with Waterslide and In-ground Spa • Ping Pong • Foosball table • Convenient location near dining and shopping • Dog friendly with approval and additional fee

8 6.5 22
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Condo

Midnight Cove II 941C

Midnight Cove II 941C

Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming with shopping, dining, art and culture. BEACH INFORMATION: Our deeded beach access is located across the street from the crosswalk. Guests should direct themselves to beach access 12 which is approximately 350 yards to the south (left) after crossing the bridge. We provide1 roll of toilet paper, 1 bar of soap in each bathroom, and 1 trash bag per trash can, but not replenished. Ride the Siesta Key Breeze Trolley it's FREE and find relief knowing you won't be driving around the village searching for a parking spot. Take a stroll to the beach via our dedicated beach access and enjoy a little sand-in-your-toes experience. Our Bayside property provides views of the Intracoastal waterway while also being within walking distance to the Gulf of Mexico. Our property offers a heated swimming pool with a large pool deck complete with lounge chairs and seating with sun shade, 2 tennis courts with 1 of them having pickle ball lines, basketball court, club house, barbecue grilling area, a beautiful observation deck at the end of our property and even private docks available to rent for your boat. During season (February and March) we have popular events that include live music, Yoga classes and much more. We are located just minutes from beautiful downtown Sarasota, the world renowned Ringling Museum of Art, as well driving distance to such attractions as Walt Disney World and Busch Gardens Tampa Bay. Sarasota is a top vacation destination in Florida and Midnight Cove II offers the perfect location and setting to enjoy it. We truly are the perfect location for your getaway. World acclaimed Siesta Beach is made famous by its sugar-fine, quartz-white sand, not to mention the thriving Siesta Village. Visit us and you will see why Siesta Key should be on your bucket list. Siesta Key beach has been ranked the best beach in America. Ready to pack up that bathing suit and a pair of flip flops? If you're looking for a condominium rental, look no further! Our sprawling tropical oasis can accommodate a minimum 7 night rental to, well, forever if you like! So, welcome aboard and let us help you begin your accommodation planning! Maybe you want to stay forever and have found your happy place? Check out our website for a listing of units for purchase. We have an agent on site that can assist you in the purchase of one of our fabulous Vacation Condominiums. This 4th floor lovely unit with a washer/dryer is a short walk to the beach and has a beautiful view of the canal and marina.

2 2 5
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House

Casa Playa

Casa Playa

Casa Playa by Siesta Key Luxury Rental Properties 3508 La Paloma Ave Sarasota FL 34242 Vacation Rental License #VR23-00001 Minimum stay duration of 7 days/nights Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! Welcome to Casa Playa, a breathtaking Mediterranean-style vacation home. The house is surrounded by lush tropical landscaping, creating a private paradise. This magnificent abode has five exquisitely designed bedrooms and three deluxe bathrooms. The dreamy backyard features a pristine pool and a remarkable tiki hut-inspired outdoor kitchen, perfect for entertaining friends and family! Beautifully designed inside, this home away from home has stunning flooring and modern updates throughout. As you step inside, you'll be greeted by a spacious living area with a large sectional and two cozy chairs. To the right, a pool table awaits. The kitchen is a chef's dream, with custom cabinetry, molding, stainless steel appliances, and ample counter space. You can entertain guests at the contemporary dining table, and outside on the terrace, you'll find plush seating and a TV for the ultimate relaxation experience. The primary bedroom feels like a dream come true, with a large bed, a workspace, and access to a balcony, but the real treat is the luxurious primary ensuite bathroom! It boasts a soaking tub, a walk-in shower, two vanities, and intricate details such as custom molding and tiles. The four guest bedrooms have TV's and are decorated with a coastal touch and have soft and crisp linens. The property has two hallway bathrooms that are spacious and contain walk-in showers. The laundry room is located near the kitchen and contains a washer and dryer. The living area has a sleeper sofa, making it comfortable for all guests. On the second floor, you will find a wet bar! Room Details -Primary Bedroom: King bed, tv, balcony access, and ensuite bathroom with walk-in shower and tub -Second Bedroom: King bed and tv -Third Bedroom: King bed and tv -Fourth Bedroom: Queen bed, tv, and balcony access - Fifth Bedroom: Queen bed -Bonus, Living Room: Queen Sleeper Sofa Stroll to Siesta Key Village to enjoy boutiques, coffee shops, fresh ice cream, and restaurants. Investigate the island with a Siesta Key tour, kayak, or paddleboard the calm intercoastal waterway and beautiful Tampa Bay, where you might encounter a dolphin or manatee or charter a fishing trip. The possibilities are endless at Casa Playa! - No pets are allowed at this property. This property has an active Ring doorbell at the main entrance. This 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. At A Glance • Less than a 10-minute walk to the beach • Private Pool • Pool Table • Tiki-bar • 2 bikes included

5 3 10
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House

Treasure on the Canal

Treasure on the Canal

Treasure on the Canal by Siesta Luxury Rental Properties 701 Treasure Boat Way Siesta Key, Florida Siesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! Welcome to Treasure on the Canal! This lavish three-bedroom, two-full-bath, plus two-half-bath haven beckons with a private pool and spa, offering blissful canal vistas. Just moments from the Gulf of Mexico's pristine shores and Siesta Key Village's charming boutiques and eateries, this retreat is the epitome of indulgence. With a private dock accommodating up to a 25-foot boat for seamless waterfront adventures, every moment promises to be a treasure to cherish. Step into luxury with this Tuscan contemporary masterpiece. The bright, open living area invites you to relax in a modern seating arrangement, complete with a smart TV. Entertain guests effortlessly at the formal dining table or indulge in a nightcap at the sleek wet bar, featuring a convenient wine fridge. The fully equipped kitchen has high-end cabinetry and stainless steel appliances, while a cozy kitchen table provides the perfect spot for intimate meals. Savor the ultimate relaxation after days spent on the water. The primary bedroom awaits with a premium mattress and ensuite bathroom featuring dual vanities, a walk-in shower, and a soaking tub. Ascend the dramatic curved staircase to discover two guest bedrooms adorned with plush bedding, conveniently adjacent to a hall bath with a shower and tub combination. A cozy bonus room on the upper level is complete with two twin beds. Additional delights include an office space, a family room complete with an extra wet bar, a laundry room, and a screened-in balcony offering serene vistas of the pool and canal. Room Details -Primary Bedroom, 1st floor: King bed and ensuite bathroom with walk-in shower and tub -Second Bedroom, 2nd floor: Queen bed -Third Bedroom, 2nd floor: King bed -Bonus Room, 2nd floor: Two Twin beds Step out to the screened-in lanai and find a bistro dining table and an outdoor kitchen setup with a built-in BBQ grill and sink. Whether you’re out exploring the water via kayak, paddleboard, or boat, lounging by the pool, indulging in nearby delights, or spending time at the beach, you will surely have an unforgettable stay at Treasure on the Canal! - This property does not allow pets. 3 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. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. This 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. Please 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. At A Glance • Canal front with private dock • Private pool with in-ground spa •15-minute walk to the beach • Screened-in patio • 30-night minimum stay

3 2.5 8
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Condo

Jamaica Royale 012

Jamaica Royale 012

Lovely 2 Bedroom/1 Bath Condo. Updated to make your stay pleasant and relaxing with all the comforts of home. Freshly painted (2021.) Games and Puzzles and loads of Beach Reading are provided. The living room features plenty of seating, including a Recliner, comfortable Sleep Sofa, and 42-inch TV (cable provided and USB port in the back if you need it.) DVD player. Washer/Dryer in the unit. Both a Keurig AND regular coffee maker are available. Ceiling fans in both bedrooms. Walk-in Shower. Free Wi-Fi. We have furnished and stocked the unit with the thought of what would we like to find when we rent a condo. We want you to enjoy your stay. Patio is only steps away from (1) of the (3) Heated Pools on the grounds. Only a short walk further and you find yourself on the soft white sand of world-famous Siesta Key Beach. Comfortable Lounge Chairs provided at the pools AND the beach. Have fun playing shuffleboard and enjoy easy access to a BBQ area. On-site management makes it easy to get questions answered and any unexpected issues addressed. Leave your car parked while here and take advantage of the many easy FREE transportation services on the island including the Trolley and Shuttle services. Bike rentals are also available in multiple locations. This unit has a 7-night minimum Saturday to Saturday rental policy but can be booked for less to fill gaps. We will do our best to accommodate any request.

2 1 6
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Condo

Siesta Beach House #303

Siesta Beach House #303

If you're looking for a great vacation location on beautiful Siesta Key, then look no further! This people-friendly complex is the perfect place to bring the family for a true holiday getaway at the beach! You'll enjoy swimming in the heated pool, taking up a game of shuffleboard, strolling along gorgeous white sandy beaches, or diving into the crystal clear waters of the Gulf of Mexico. It is located on a private lane that leads right to the beach. There is no traffic and no streets to cross, just a short stroll to the famed white sands of Crescent Beach on Siesta Key, Florida.

2 1.5 6
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