Vacation Rentals By Owner In Siesta Key, FL

2 BR.-- 2 BA -- 4 Person Max -- Large Garden -- Pond View -- Approximately 150 yards away from Crescent BeachbrbrThis property is a 30 night minimum. brThis unit is a 2nd floor walk-up Large Garden unit. Very open and airy. brThis unit is a 2 bedroom, 2 full bathroom unit, located on the Gulf-side.brThe kitchen offers an open concept kitchen, including breakfast bar. brComfortably sleeps 4 with a king bed in the master bedroom and 2 twin beds in the guest bedroom. brThe serene views of the Peppertree pond from the lanai, combined with the fresh earth toned decor of the condo, providing the ultimate relaxation oasis. brThe master bathroom has a shower with built in shower seat and the guest bathroom has a tub/shower combo. brThis unit has access to a private garage. No elevators but with stairs access. brInternet access, beach access, tennis court, fitness center, sauna and access to two heated swimming pools included. No pets are permitted on the property.

1077 PD - Standard - Large Garden Oasis Condo

Siesta Key, Florida, United States

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$252.19

Indulge in coastal luxury with this beautifully decorated Gulfside unit nestled on the 1st floor of a stunning high-rise. With hardwood floors throughout and thoughtfully curated decor, this retreat offers the perfect blend of elegance and comfort.brbrStep into the spacious living area, where natural light floods through large windows, illuminating the stylish furnishings and inviting ambiance. The open-concept layout seamlessly connects the living, dining, and fully equipped kitchen areas, creating an ideal space for entertaining or unwinding after a day of beachside adventures.brbrThe fully equipped kitchen features modern appliances, sleek countertops, and ample cabinet space, making it a delight for both casual cooks and culinary enthusiasts alike. brbrRetreat to the master bedroom, where serenity awaits in the form of a luxurious king-size bed and an en suite bathroom. brbrThe guest bedroom offers two comfortable twin beds, perfect for accommodating family or friends. A second bathroom located in the hallway ensures convenience and privacy for all guests.brbrConvenience meets functionality with the inclusion of a full-size washer and dryer, allowing you to keep your beachwear fresh and clean throughout your stay. Plus, enjoy the added convenience of a covered parking space, providing protection from the elements.brbrImmerse yourself in the beachside lifestyle, with direct access to the pristine shores and a wealth of amenities at your fingertips. Whether you're lounging by the pool, exploring nearby attractions, or simply soaking in the sunset. this Gulfside retreat promises an unforgettable vacation experience.brbrDon't miss out on the opportunity to experience coastal living at its finest. Book your stay in this beautifully appointed unit today and create memories that will last a lifetime!brbr30 night minimum

1055-106 Fully Renovated Condo in Paradise

Siesta Key, Florida, United States

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$334.61

2 BR -- 2 BA -- 6 Person Max -- High Rise -- Pond brbrThis property is a 30 night minimum. br1125 - 705 is a high-rise unit, located on the Gulf-side of Midnight Pass, approx.175 yards away from Crescent beach. brOpen kitchen floor plan. Newly remodeled kitchen with stainless steel appliances. Dual sink vanity in the Master bathroom. Assigned covered parking located in parking garage. brApprox. 1200 Sq. Ft. (1480 including the lanai). brbrCondo Summary: Bedding: Master Bedroom: King - Guest Bedroom: 2 Twins brElectronics: Living room: 65 Smart TV - Master Bedroom: 42 Smart TV - Guest Bedroom: 42 Smart TV brBathrooms: Master: Shower - Guest: Shower

1125-705 - Premium - Enjoy Seaside Splendor

Siesta Key, Florida, United States

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$262.39

2 BR -- 2 BA -- 6 Person Max -- High Rise -- Greenbelt View brbrThis property is a 30 night minimum. br1080 - 701 is a Gulf-side High-rise unit, located approximately 125 yards away from Crescent Beach brCan be combined with 1080-702 for larger groups. Assigned covered parking located in parking garage. brApprox. 1250 Sq. Ft. (1375 including the lanai) brbrCondo Summary: brBedding: Master Bedroom: King - Guest Bedroom: 2 Twins brElectronics: Living-room: 42 inch Flat Panel - Master Bedroom: 28 inch Flat Panel br Guest Bedroom: 28 inch Flat Panel brBathrooms: Master: Tub/Shower (removable shower head ) - Guest: Shower - (with grab bars)

1080-701 - Standard Plus - Tropical Garden Paradise Found

Siesta Key, Florida, United States

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$230.73

2 BR -- 2 BA -- 6 Person Max -- High-rise -- Greenbelt View brbrThis property is a 30 night minimum. br1080 - 702 is a Gulf-side High-rise unit, located approximately 125 yards away from Crescent Beach.brStainless steel refrigerator & assigned covered parking located in parking garage. brCan be combined with 1080-701 for larger groups.brApprox. 1250 Sq. Ft. (1375 including the lanai) brbr brCondo Summary:brBedding: Master Bedroom: King - Guest Bedroom: 2 Twins brElectronics: Living-room: 50 inch Flat Panel - Master Bedroom: 32 inch Flat Panel br Guest Bedroom: 28 inch Flat Panel brBathrooms: Master: Tub/Shower (with grab bars & removable shower head) - Guest: Shower (with grab bars)

1080-702 -Standard Plus - Escape to Tropical Tranquility

Siesta Key, Florida, United States

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$273.61

2 BR -- 2 BA -- 6 Person Max -- Large Garden -- Pond View brbrThis property is a 30 night minimum. brThis 2 bedroom, 2 bath is a large garden unit on the gulf-side and is approximately 175 yards from Crescent Beach. brThe master bedroom has a king bed, a 32 inch TV, a ceiling fan, and plenty of natural light. The master bathroom is a walk in with glass shower doors and grab bars. brThe guest bedroom has a queen bed, a 32 inch TV, and a ceiling fan. The guest bathroom has a shower/tub combination. brThe kitchen is complete for all your cooking needs. The dining area fits 6 chairs, with an additional chair available. The dining area flows easily into the living space that has plenty of comfortable seating to enjoy. The living room has a 46 inch TV and two large sliding glass doorways to the lanai that allow the natural light to fill the room. The living room also has a sleeper sofa to accommodate 2 people. brThe lanai offers beautiful views of the garden and has an additional dining and seating. brThis unit has access to a private garage and has an in-unit washer and dryer. brApprox. 1250 Sq. Ft. (1375 including the lanai) brbrCondo Summary:brBedding: Master Bedroom: King - Guest Bedroom: 2 Twins brElectronics: Living-room: 40 inch Flat Panel - Master Bedroom: 28 inch Flat Panel br Guest Bedroom: 28 inch Flat Panel brBathrooms: Master: Shower - Guest: Tub/Shower

1114 PC Seaside Sanctuary Awaits

Siesta Key, Florida, United States

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$325.07

New photos coming soon! Villa 51 at Aloha Kai is a beautifully updated retreat that offers the perfect setting for your beach getaway. Begin your day with coffee in the light and airy kitchen, then step out to enjoy it on your private front porch or back patio. The spacious living room features designer plantation shutters on the sliding doors, providing both elegance and privacy. The bedroom offers generous closet space, while the spa-inspired bathroom includes a walk-in shower for a touch of luxury. Located on Siesta Key—a popular barrier island on Florida’s West Coast—Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The three-mile stretch of Crescent Beach and the clear Gulf waters provide the perfect backdrop for soul-soothing walks and unforgettable sunsets. Aloha Kai invites you to relax under shaded beach pavilions or unwind by the largest pool on Siesta Key.brbrPlease note: This villa is equipped with two video surveillance cameras located in the carport, monitoring the front door, front porch, and back door of the property. These cameras are owner-monitored. Management does not have access to the footage.

Villa 51 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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Select Dates for Price

This property is a 30 night minimum. Welcome to your perfect vacation retreat! This beautifully appointed 3-bedroom, 2-bathroom condo offers the ideal blend of comfort, style, and convenience. Situated in a prime location, this property provides the perfect base for your getaway, whether you’re seeking relaxation, adventure, or a little of both.brbrStep inside to find a spacious open-concept living area featuring comfortable seating, a large flat-screen TV, and plenty of natural light. The fully equipped kitchen boasts stainless steel appliances. A dining area with seating for six makes family meals or game nights a breeze.brbrEach of the three bedrooms is thoughtfully designed for relaxation and privacy. The primary suite features a plush king-sized bed, a private ensuite bathroom, and access to a balcony where you can enjoy your morning coffee or evening cocktails. The second bedroom includes a queen-sized bed, while the third offers two twin beds, perfect for children or additional guests. A second full bathroom ensures everyone has space to refresh and unwind.brbrThe condo is located in a resort-style community with amenities such as a sparkling pool, hot tub, fitness center, and direct access to nearby attractions.brbrJust minutes from Siesta Key Village, this condo offers the perfect combination of relaxation and adventure. Whether you're here to soak up the sun, explore local attractions, or simply unwind with family and friends, this property is the perfect home base for your vacation.brbrBook now to experience the comfort and convenience of this exceptional 3-bedroom condo! We look forward to hosting you.

6044 WPW 3 Bedroom Condo Steps From the Pool

Siesta Key, Florida, United States

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$463.48

Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience.brbrStep into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it ideal for both relaxing evenings in and entertaining guests.brbrThe fully equipped kitchen boasts modern appliances, sleek countertops, and ample cabinet space, providing everything you need to unleash your inner chef. Whip up delicious meals and enjoy them at the adjacent dining area, or take your culinary creations outside to the charming patio overlooking the sparkling pool.brbrRetreat to the master bedroom, featuring a luxurious king-size bed and an en suite bathroom for added privacy and convenience. Pamper yourself in the spa-like surroundings, complete with a walk-in shower and elegant fixtures.brbrThe guest bedroom offers two comfortable double-size beds, perfect for accommodating family or friends. A second bathroom located in the hallway ensures everyone has plenty of space and amenities to feel at home.brbrConvenience meets functionality with the inclusion of a full-size washer and dryer, allowing you to keep your wardrobe fresh and clean throughout your stay.brbrImmerse yourself in the vibrant community atmosphere, with easy access to the pool and other shared amenities. Whether you're lounging by the poolside or exploring the nearby attractions, this condo provides the perfect home base for your vacation.brbrDon't miss out on the opportunity to experience the ultimate in comfort and style. Book your stay in this brilliantly decorated condo today and make unforgettable memories in paradise!

6046 Large Garden Unit

Siesta Key, Florida, United States

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$188.96

2 BR - 2 BA - 6 Person Max - High-rise - Greenbelt View brbrThis property is a 30 night minimum. br1255 - 306 is a Bay-side Mid-rise unit, located approximately 75 yards away from the Bay. brHardwood floors on the lanai. Assigned covered parking located in parking garage. brApprox. 1250 Sq. Ft. (1375 including the lanai) brbrCondo Summary: brBedding: Master Bedroom: King - Guest Bedroom: Queen brElectronics: Living-room: 36 inch Flat Screen - Master Bedroom: 20 inch Flat Screenbr Guest Bedroom: 12 inch Flat ScreenbrBathrooms: Master: Tub/Shower (with grab bars) - Guest: Shower (with grab bars)

1255-306 - Standard - Stroll to Warm Bay Breezes

Siesta Key, Florida, United States

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Select Dates for Price

2 BR - 2 BA - 6 Person Max - High Rise - Gulf View brbrThis property is a 30 night minimum. br1200-607 is a Bay-side Mid-rise unit, with a view of the Gulf from the large lanai. Located approximately 150 yards away from the BaybrRemodeled kitchen with stainless steel appliances. Shower seat in the Master bathroom. Assigned covered parking located in parking garage. brApprox. 1250 Sq. Ft. (1375 including the lanai) brbrCondo Summary:brBedding: Master Bedroom: King - Guest Bedroom: Queen brElectronics: Living-room: 40 inch Flat Panel - Master Bedroom: 30 inch Flat Panel br Guest Bedroom: 24 inch Flat Panel brBathrooms: Master: Shower - Guest: Tub/Shower

1200-607 - Standard - Enjoy Relaxing Bayfront Bliss

Siesta Key, Florida, United States

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$228.42

2 BR - 2 BA - 6 Person Max - Mid-rise - Gulf View and City View brbrThis property is a 30 night minimum. brThis stunning, updated 2 bedroom, 2 bath is located in a bay-side mid-rise unit and is approximately 75 yards from the bay. brThe master bedroom has a king bed, a TV, and pocket sliding glass doors that gives access to the extended lanai living. The master bathroom has a walk-in glass door shower with grab bars and a beautiful granite vanity. brThe guest bedroom has a Murphy bed, a TV, a couch, a keyboard, and an in window retreat area to enjoy the view or a book. The guest bathroom has a shower. brThe kitchen has updated stainless steel appliances, counters, cabinetry, and recessed lighting. This open concept unit allows for cooking and entertainment to flow seamlessly with the kitchen connecting to the dining and living area. brThe modern dining table has service for 6 and updated lighting. The living room offers a stylish and comfortable retreat after the long day, with attractive seating, a large TV, and pocket sliding doors allowing seamless access to the extended living lanai. The living room has an EXTRA large Queen pull out sleeper sofa. brThe lanai has been transformed into a second living space with an additional dining area, a bold but cozy couch, ceiling fans, and a stunning view of the gulf, gardens, and Peppertree Bay. There is also a work space available in the lanai. brThis unit has an assigned parking garage spot under the building and an in-unit washer and dryer. This unit is accessible by elevator or stairs.

1255-403 - Premium - Panoramic Paradise with Gulf and City Views

Siesta Key, Florida, United States

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$279.86

3 BR. - 3 BA -- 6 Person Max. -- Townhouse -- Greenbelt View brbrThis property is a 30 night minimum. brbrThis 3 bedroom, 3 bath is a townhouse on the bay side of Midnight Pass and is approximately 100 yards from the Intracoastal waterway. brThe master bedroom has a king bed, a large TV, a ceiling fan, and an en suite bathroom. The master bathroom has a quartz counter, recessed lighting, and a tub/shower combination. brThe first guest bedroom has a queen bed, a ceiling fan, and a 3/4 guest bathroom. brThe third bedroom has 2 twin beds, and the bathroom has a walk-in glass sliding door shower and updated features. brThe kitchen has recently been fully updated with all new appliances and quartz countertops brThe dining room has seating for 6 and flows openly to the living area. The living area has comfortable couch seating, a 55 inch Flat Panel, a ceiling fan, and the lanai doors allow for plenty of natural light to enter in. brThe lanai is a space to relax bug-protected, with a dinette, and views of the garden. brThis unit has an interior set of stairs, an assigned parking spot, and has a new washer and dryer. brApprox. 1400 Sq. Ft. (1500 including the lanai) brbrCondo Summary: brBedding: Master Bedroom: King - Guest Bedroom: 1 Queen - 2nd Guest Bedroom: 2 Twins brElectronics: Living-room: 55 inch Flat Panel, Master Bedroom: 36 flat panel,brGuest Bedroom: 27 flat panel. brBathrooms: Master: Tub/Shower - Guest: Shower

1207 PD - Premium - Bayside 2-story

Siesta Key, Florida, United States

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$221.65

2 BR - 2 BA - West Water View- High-risebrbrThis property is a 30 night minimum. brbrCentral property, High-rise style unit with 2 Bedrooms and 2 Bathrooms. All rental properties are turn-key furnished and include washer & dryer. Fully equipped kitchens, Internet access, beach access, tennis courts and exercise facilities available, access to two swimming pools. No pets are permitted on the property.

1200-406 - Standard Plus - Embrace Spectacular Water Views

Siesta Key, Florida, United States

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$252.19

2 BR -- 2 BA -- 6 person Max -- Small Garden -- Greenbelt View -- Second floor unit. brbrThis property is a 30 night minimum.brbr1156 is a small garden unit, located on the Gulfside of Midnight Pass Roadbrbr2 bedroom, 2 bath unit . Approx. 1100 Sq. Ft. (1200 including the lanai).brbrThis is a new condo on the Rental Program. It has been completely renovated in 2023.brbrBoth bedrooms have a Queen size bed with wall mounted Tv’s for your entertainment. brbrBoth bathrooms have been renovated and has a walk-in shower with Happy Floor tiles with Frontgate bath towels and Frontgate beach towels.brbrThere is an added bar on the lanai area and has been incorporated with the living room. brbrPottery Barn queen size sleeper sofa with memory foam mattress. All other furniture is high-end from Arhaus.brbrThe condo also has a Reverse Osmosis water tap.brbrOther items included:br-Yeti Cooler (large)br- Additional backpack coolerbr- Beach cartbr- 2 Fishing poles (net, tacklebox) br- Beach games: Spikeball & Pro Kadima paddle set (4 paddles)brbrThere are stairs to access the condo, which is on the second floor.brbrParking is included.brbrNo pets allowed.

1156 PD - Premium - Luxuriously Renovated Oasis

Siesta Key, Florida, United States

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$600.41

Villa 61 at Aloha Kai warmly welcomes you with its cheerful coastal décor, designed to help you forget your worries and simply be happy. Its casual, comfortable style will make you feel right at home, while offering the luxury of both beach and pool access—you’ll just have to decide which you prefer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the perfect backdrop for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 61 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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Exceptional(1)

$420.72

Villa 54 at Aloha Kai is your ideal beach retreat, spacious, sun-filled, and designed for total relaxation. This corner villa features an open floor plan with abundant natural light, custom cabinetry, and thoughtful upgrades throughout. The updated kitchen includes stainless steel appliances and is fully equipped to make meal prep easy, while the in-unit washer and dryer add everyday convenience during your stay. Enjoy the comfort of an Insta-hot water heater, a walk-in shower, a half bath in the master bedroom, and three TVs for your entertainment. Whether you're lounging on the porch, soaking up the sun by the pool, or taking a short stroll to the beach, this is your place to unwind at your own pace. Located within the gated, family-friendly Aloha Kai community on Siesta Key, Florida’s beloved barrier island, Villa 54 is just steps from world-renowned Crescent Beach, famous for its powdery white quartz sand and emerald-green waters. Frequently ranked the number one beach in the continental United States, this breathtaking stretch of shoreline offers soul-soothing walks and unforgettable sunsets. Aloha Kai completes your vacation experience with shaded beach pavilions and the largest pool on Siesta Key. Whether you're seeking a peaceful escape or a fun-filled getaway, Villa 54 offers the perfect setting for creating lasting memories.

Villa 54 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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$593.8

Light, bright, and beachy—Villa 56 at Aloha Kai welcomes you with its retro charm and casual coastal elegance. The inviting interior is enhanced by an updated bath that offers a spa-like retreat, perfect for unwinding after a sun-soaked day at the beach or an afternoon exploring the shops and restaurants in town. In the evening, enjoy a peaceful sunset stroll along the shoreline, then return to your villa to relax on the porch with your favorite drink in hand, soaking in the balmy coastal breeze. For added convenience, the villa includes a washer and dryer. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community in the heart of Crescent Beach—ranked the number one beach in the continental United States. Known for its powdery white quartz sand and shimmering emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico create the perfect backdrop for soul-soothing walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, offering the ultimate setting for a relaxed, laid-back beach vacation.

Villa 56 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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$605.67