Vacation Rentals By Owner In Siesta Key, FL

Aloha Kai #62brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #62. This adorable 1 bedroom, 1 bath unit is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Unveiling boundless joy in a snug sanctuary, Aloha Kai #62 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br1 Bedroom:brMaster Suite: King-size bed and Smart TVbrAdditional Sleep: Queen-size sleep sofa in the lounge areabrTop Features:brSleeps 4brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brFront Screened Porch and Back Patio: Sip coffee in the mornings in your screened porch or curl up with a good book. Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #62 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #62 today and create memories that will last a lifetime!brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brbrDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Unveiling Joyful Beachside Moments – Aloha Kai #62 - Roelens

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$372.74

Aloha Kai #37brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #37. This charming beach 2-bedroom house is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Maximizing comfort in a cozy layout, Aloha Kai #37 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br2 Bedrooms:brMaster Bedroom with King-size bed, Smart TV and Ensuite BathroombrGuest Bedroom 1 with 2 Twin-size beds, Smart TVbrAdditional Sleep: Sleep Sofa in the living area.brTop Features:brSleeps 6brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brFront Screened Porch and Back Patio: Sip coffee in the mornings in your screened porch or curl up with a good book. Enjoy balmy evenings at home on the back patio to relax and unwind after an eventful day.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #37 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #37 today and create memories that will last a lifetime!brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Cozy Home Near the Beach - Aloha Kai #37 - Roelens

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$237.0

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrBayfront Comfort with Modern Style | 2BR, 2.5BA Condo in Bay Oaks, Siesta Key brbr brbrJust a short walk to Crescent Beach, this renovated 2-bedroom, 2.5-bath condo in Bay Oaks offers the perfect mix of island relaxation and resort-style recreation – with serene bay views, tropical surroundings, and a full suite of amenities. brbr brbrLOCATION HIGHTLIGHTS: brbr- 7-minute bike ride to Siesta Key Beach brbr- 14-minute walk to Crescent Beach (#12 beach access) brbr- Short drive to restaurants and shops brbr- Short drive to downtown Sarasota, Venice, Golf, marinas, and cultural attractions brbr- Private fishing pier – perfect for dolphin watching and evening strolls brbr- Heated community pool and tennis court brbr- Billiards room & clubhouse, BBQ area with picnic tables brbr- Tropical landscaping and scenic walking paths brbr- Assigned covered parking space brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 2.5 Bathroom, 2 floor condo brbr- Over 1,190 sq ft of updated living space brbr- Private screened-in balcony with views of the pool & palm-lined paths brbr- Stunning sunrises and fresh sea air from the second-floor unit (stairs only) brbr- Central A/C with ceiling fans brbr- In unit laundry room brbr- Dedicated WIFI with cable brbr brbrLIVING ROOM: brbr- Coastal decor and furnishing brbr- Mounted TV with cable channels brbr- Direct access to the screened balcony with outdoor furniture brbr- Comfy couch that doubles as a sofa bed brbr brbrKITCHEN AND DINING: brbr- Modern kitchen with Stainless steel appliances, French door refrigerator, glass-top stove and dishwasher brbr- Breakfast bar seating + dining table for 6 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom (upstairs): King-size bed, private balcony with seating, walk-in closet and en-suite bathroom with step-in tub/shower combo brbr- Guest bedroom (upstairs): Two queen beds, walk-in closet, renovated en-suite bathroom with tub/shower combo brbr- Half bath (downstairs): wash room conveniently located between the living and dining rooms brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, beach umbrella, and beach towels brbr brbrNEARBY FAVORITES: brbr- Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery, and more within walking distance brbr- Boat & water sport rentals nearby brbr- Post office close by for sending postcards home brbr brbrIMPORTANT INFORMATION: brbr- No pets allowed brbr- Rental registration form required brbr- Stairs only – no elevator access brbr- Parking restrictions apply, no boats, motorcycles, kayaks, trailers, oversized vehicles, or commercial vehicles. Ask us before booking! brbr brbrYOUR PERFECT BEACH GETAWAY IS WAITING - SEE YOU SOON!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.brbrIMPORTANT: brbrCarport repair and paving project scheduled to start end of April/early May, 2026. Parking will be disrupted. Please each out for more info.

Bayfront Balconies in Tropical Siesta Key with Sunrise Views & Walkable Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$242.47

Harbor Towers Unit 302 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 302, a recently refreshed two-bedroom, two-bath vacation condo located on scenic Midnight Pass Road in Siesta Key. Set within the desirable Harbor Towers community, this inviting retreat is ideal for couples, friends, or small families seeking a comfortable extended stay near Siesta Key Beach, dining, and island attractions. With bright coastal interiors, a screened lanai, and a thoughtful layout, this condo offers the perfect blend of relaxation and convenience.brbrHighlightsbr• Two-bedroom, two-bath condobr• King bed, two twin beds, queen sofa sleeperbr• Washer and dryer in unitbr• 13-night minimum stay communitybr• Screened lanai with seatingbr• Recently refreshed interiorbr• Gated waterfront Harbor Towers communitybr• Two heated pools and three Har-Tru tennis courtsbr• Marina, fitness center, and saunabrbrEnjoy peaceful mornings and breezy evenings on the screened lanai, a lovely extension of the living space that provides a comfortable spot to unwind with coffee or a good book. As part of the Harbor Towers community, guests can enjoy access to well maintained shared amenities throughout the property, making this condo an excellent choice for longer stays on Siesta Key.brbrThe open concept living area is designed for comfort and ease, featuring cozy seating, tile flooring, and a queen sofa sleeper for additional guests. The living space flows naturally into the dining area and kitchen, creating a welcoming environment for relaxing after a day at the beach or sharing meals together. The kitchen is bright and functional, offering ample counter space, cabinetry, and essential appliances to support everything from quick breakfasts to home-cooked dinners during your stay.brbrThe primary bedroom is a relaxing retreat featuring a king bed, ample closet space, and a private ensuite bathroom. The second bedroom offers two twin beds and convenient access to the hallway bathroom, making it ideal for children or additional guests. Both bathrooms are thoughtfully laid out to provide comfort and functionality throughout your stay.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Second Bedroom: Two twin bedsbr• Living Area: Queen sofa sleeperbr• Hallway Bathroom: Shared accessbrbrThis condo includes an in-unit washer and dryer, adding everyday convenience for extended stays. Elevator access and well kept community grounds further enhance the guest experience at Harbor Towers.brbrWhether you are planning a relaxing seasonal escape or a longer Siesta Key getaway, Harbor Towers Unit 302 by Tropical Sands Accommodations offers a welcoming home base in a prime island location. Secure your dates today and start looking forward to sun-soaked days, coastal breezes, and easy island living.

Harbor Towers 302 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$249.27

Harbor Towers Unit 216 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 216, a beautifully updated two-bedroom, two-bathroom condo in one of Siesta Key’s most sought-after gated waterfront communities. Perfect for extended stays with a 13-night minimum requirement, this inviting retreat offers comfortable coastal interiors, resort-style amenities, and a prime location just minutes from the world-famous Siesta Key Beach and Siesta Key Village.brbrHighlights:br• 2 Bedroom / 2 Bathroom condobr• King, Full, Queen sleeper sofabr• 13-night minimum stay communitybr• Short drive to Siesta Key Beachbr• Gated waterfront communitybr• 2 heated community poolsbr• 3 Har-Tru tennis courtsbr• 40-slip marinabr• Fitness center and saunabr• Convenient location near Siesta Key Village dining and shoppingbrbrHarbor Towers is known for its exceptional community amenities that set it apart from many Siesta Key associations. Guests enjoy access to two heated pools, ideal for morning swims or relaxing afternoons in the Florida sunshine. Tennis enthusiasts will appreciate the three tennis courts, while boating lovers can take advantage of the 40-slip marina. This gated waterfront community also features a fitness center and sauna, making it an ideal choice for extended stay guests who want both recreation and relaxation during their time on Siesta Key.brbrUnit 216 welcomes you with a bright and comfortable living area featuring plush seating and a queen sleeper sofa, providing additional sleeping space for guests. Large windows bring in natural light, creating a relaxed coastal atmosphere perfect for longer stays. The fully equipped kitchen offers stainless steel appliances, ample cabinetry, and all the cookware and utensils needed to prepare meals with ease. Whether you are cooking dinner after a beach day or enjoying morning coffee before heading to the pool, this space is designed for convenience. The adjacent dining area provides a comfortable setting for shared meals or casual gatherings.brbrThe primary bedroom features a king bed, generous closet space, and a private ensuite bathroom with a walk-in shower and dual vanity, offering both comfort and privacy. The second bedroom includes a full bed and easy access to the hallway bathroom, which features a shower and tub combination. With the additional queen sleeper sofa in the living room, this condo comfortably accommodates couples, small families, or extended stay guests hosting visitors. Each bedroom is thoughtfully designed to provide a restful and relaxing environment after a day spent enjoying Siesta Key.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in showerbr• Second Bedroom: Full bedbr• Living Room: Queen sleeper sofabr• Hallway Bathroom: Shower and tub combinationbrbrHarbor Towers Unit 216 includes access to community grilling areas, beautifully maintained grounds, and direct access to the Intracoastal Waterway. The 13-night minimum stay policy creates a peaceful environment ideal for seasonal guests, remote workers, and snowbirds seeking a longer Siesta Key escape.brbrIf you are looking for a Siesta Key vacation rental that offers resort style amenities, a prime waterfront location, and the comfort of an extended stay condo, Harbor Towers Unit 216 by Tropical Sands Accommodations is the perfect choice. Secure your preferred dates today and start planning your coastal retreat in beautiful Siesta Key.

Harbor Towers 216 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$207.68

Harbor Towers Unit 312 by Tropical Sands AccommodationsbrbrHarbor Towers Unit 312 is a freshly remodeled one-bedroom, one-bath condominium offering marina views and modern upgrades throughout within the Harbor Towers Yacht and Racquet Club. This bright residence features new furnishings, flexible sleeping accommodations, and a comfortable layout ideal for an extended Siesta Key stay.brbrHighlightsbr• 13-night minimum staybr• 1 Bedroom / 1 Bathroombr• Sleeps up to 4 guestsbr• King bed and Murphy bedbr• Marina viewsbr• Freshly remodeled interiorbr• New furniture and vinyl flooring throughoutbr• Fully equipped kitchen with stainless steel appliancesbr• Laundry room located directly across the hallbr• Gated waterfront communitybr• Two heated pools and three Har-Tru tennis courtsbrbrGuests at Unit 312 enjoy access to Harbor Towers’ resort style amenities, including two heated swimming pools, three Har-Tru tennis courts, and a 40-slip marina along the Intracoastal Waterway. Fitness and sauna facilities, shared grilling areas, and scenic waterfront seating throughout the community create a relaxed island atmosphere designed for longer stays.brbrThe condo offers a comfortable and efficient floor plan designed for relaxation and ease. The living area features a cozy sectional, a flat-screen TV with HD cable, and a Murphy bed, allowing the space to accommodate additional guests. The living area flows into a fully equipped kitchen with granite countertops, new stainless steel appliances, and a coffee machine, making it easy to prepare meals during your stay. A dining table for four provides a welcoming space for meals and gatherings.brbrThe primary bedroom features a brand new king mattress, ample closet and dresser storage, and a flat-screen TV with HD cable. The bathroom includes a walk-in shower with a built-in Bluetooth speaker, adding a unique and modern touch to the space. Bed linens and bath towels are provided for guest convenience.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Living Area: Murphy bedbrbrWith its fresh renovations, marina views, and access to Harbor Towers’ exceptional waterfront amenities, Harbor Towers Unit 312 by Tropical Sands Accommodations is a welcoming retreat on Siesta Key. Enjoy morning coffee overlooking the marina, take advantage of the nearby trolley stop, and settle into the easy rhythm of island living. Book your extended stay and make this your coastal home away from home.

Harbor Towers 312 - Tropical Sands Accommodations

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$242.14

Harbor Towers Unit 321 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 321, a spacious one-bedroom, one-bath condo in one of Siesta Key’s most desirable gated waterfront communities. Perfect for couples, seasonal guests, or extended stays with a 13-night minimum requirement, this inviting retreat offers scenic views, a bright enclosed lanai, and access to resort-style amenities just minutes from Siesta Key Beach and Siesta Key Village.brbrHighlightsbr• 1 Bedroom / 1 Bathroom condobr• King bedbr• 13-night minimum stay communitybr• Short drive to Siesta Key Beachbr• Enclosed lanai with panoramic viewsbr• Gated waterfront communitybr• 2 heated community poolsbr• 3 Har-Tru tennis courtsbr• 40-slip marinabr• Fitness center and saunabrbrHarbor Towers is known for offering amenities rarely found in many Siesta Key associations. Guests enjoy two heated pools, ideal for relaxing year round, along with three tennis courts for those who enjoy staying active. The 40-slip marina provides direct access to the Intracoastal Waterway, and the gated community also features a fitness center and sauna. For extended stay guests and snowbirds, these amenities make Harbor Towers a standout choice for comfort and recreation.brbrInside Unit 321, the enclosed corner lanai is the highlight. Surrounded by large windows, this bright dining and sitting space offers beautiful views and abundant natural light, creating the perfect setting for morning coffee or sunset dinners. The open living and dining area feels spacious and welcoming, with comfortable seating and a television for relaxing evenings. The enclosed lanai extends the living space and provides a peaceful vantage point overlooking the surrounding area. The kitchen offers generous cabinet storage, full-size appliances, and ample counter space for preparing meals with ease. Whether you are staying for a few weeks or a seasonal visit, this layout supports both comfort and functionality.brbrThe primary bedroom features a king bed, large windows with natural light, and ample storage space. The ensuite bathroom includes a spacious vanity and a shower and tub combination for added convenience. Designed with extended stay guests in mind, the bedroom offers a restful and private retreat after a day at Siesta Key Beach or exploring the Village.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with shower and tub combinationbrbrHarbor Towers Unit 321 offers elevator access, beautifully maintained grounds, community grilling areas, and assigned parking. The 13-night minimum stay requirement ensures a quieter, more residential atmosphere, ideal for couples, snowbirds, and remote workers seeking a longer Siesta Key getaway.brbrIf you are looking for a Siesta Key condo rental that offers resort-style amenities, scenic views, and the comfort of an extended stay community, Harbor Towers Unit 321 by Tropical Sands Accommodations is the perfect choice. Reserve your preferred dates today and experience the relaxed coastal lifestyle that makes Siesta Key a favorite year after year.

Harbor Towers 321 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$349.72

Welcome to Ocean Beach Gleason Home! brbr brbrNewly renovated and furnished! New pics to come! brbr brbrThis beautiful 4-bedroom, 2-bathroom home on Siesta Key is perfect for families or groups looking for a luxurious and relaxing getaway. With over 1,900 square feet of heated space and a total of 2,500 square feet, this single-level home offers plenty of room to spread out. The property features a private saltwater pool and spa, with optional heating, overlooking a serene lake, providing a picturesque backdrop for your stay. brbr brbrLOCATION HIGHLIGHTS: brbr- 6-minute bike ride to Siesta Key Beach brbr- Close to Siesta Key Village dining and shops brbr- Peaceful lakefront setting brbr- Quiet residential neighborhood brbr- Easy access to island hotspots brbr brbrPROPERTY FEATURES: brbr- 4 bedrooms, 2 bathrooms pool home brbr- Private saltwater pool and spa (pool heat extra) brbr- Lake views from pool and patio brbr- Outdoor seating, loungers, and BBQ grill brbr- Pet-friendly for approved dog only (fee required) brbr- Dedicated WIFI and cable brbr- Self check in, keyless door lock brbr- Separate private washer and dryer room brbr brbrLIVING ROOM: brbr- Large flat-screen TV, comfortable seating for group lounging brbr- Sliding doors to pool area brbr- Open and bright layout brbr brbrKITCHEN AND DINING: brbr- High-end appliances with stone countertops and breakfast nook brbr- Dining table seats eight brbr- Open flow to patio and pool area brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom with king bed, custom closet, and ensuite bath brbr- Master ensuite bathroom: Step-in shower, large mirror, updated vanity brbr- Second bedroom with queen bed and Smart TV brbr- Third bedroom with king bed and Smart TV brbr- Fourth bedroom with king and pool access brbr- Guest bathroom: double vanity, tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach for powdery white sand brbr- Siesta Key Village for restaurants and nightlife brbr- Scenic bike rides around the island brbr- Waterfront dining options nearby brbr brbrIMPORTANT INFO: brbr- Pool heating available for an extra fee brbr- Dog allowed with prior approval and fee (no cats) brbr- No smoking inside or on patio brbr- Respect residential area and quiet hours brbr brbrCLICK BOOK NOW AND GET CLOSER TO THE COASTLINEbrbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Walkable to Siesta Key Village, Saltwater Pool/Spa, BBQ, Pond Views, Bike to Beach in 6 mins

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$487.15

Sunshine on Siesta – by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sunshine on Siesta, a recently refreshed four-bedroom, two-bath Super Unit designed for families and groups who want to vacation together while enjoying space, comfort, and an unbeatable Siesta Key location. By combining both the Sunrise and Sunset residences, this home offers a unique opportunity to book the entire property at once, making it ideal for multi-generational families or friends traveling as a group.brbrLocated just steps from the Gulf, Sunshine on Siesta provides private beach access and a relaxed coastal setting close to Siesta Key Village, local dining, and shopping. This thoughtfully arranged home allows guests to enjoy shared experiences while still having room to spread out and unwind.brbrHighlightsbr• Private beach access – 5 minute walkbr• 4 Bedrooms / 2 Bathroomsbr• 2 King beds and 4 Twin bedsbr• Recently refreshed homebr• Shared pool with neighboring condominium – 2 minute walk br• Beach chairs and beach cartbr• Shared firepitbr• Washer and dryerbr• Pets allowed with host approval br• 2 Parking spotsbr• Convenient Siesta Key location near dining and shoppingbrbrSunshine on Siesta offers convenient access to shared amenities designed for relaxed island living. The shared pool is located just a two-minute walk from the home at the Calini Beach Club, which also provides private beach access about five minutes away. A shared laundry area sits between the two duplex residences, making it easy for guests booking the full Super Unit to use. The shared backyard includes a BBQ grill and a cozy firepit seating area, perfect for unwinding after a day at the beach.brbrThe Super Unit features two comfortable living areas, making it easy for larger groups to relax without feeling crowded. Each side of the home includes inviting seating and a television, perfect for movie nights or quiet evenings in. The kitchens are equipped for everyday cooking, making it easy to prepare meals, snacks, or beach-day essentials while enjoying time together indoors.brbrEach side of the home includes a primary bedroom with a king bed, offering a calm and comfortable retreat at the end of the day. The additional bedrooms feature twin beds, making them ideal for children or additional guests. Bathrooms are conveniently located and feature walk-in showers, providing easy access for everyone in the group.brbrRoom Detailsbr• Primary Bedroom 1: King bedbr• Primary Bedroom 2: King bedbr• Bedroom 3: Two twin bedsbr• Bedroom 4: Two twin bedsbrbrSunshine on Siesta by Siesta Key Luxury Rental Properties delivers the space of a private compound with the ease of private beach access and shared outdoor amenities. Whether you are planning a family reunion or a group getaway, this Super Unit offers comfort, location, and a true Siesta Key experience. Secure your dates today and start planning your coastal escape.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith 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. brbr2 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. brbrWe 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 see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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.

Sunshine on Siesta - Refreshed Duplex!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$604.61

Sunrise by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sunrise, a recently refreshed two-bedroom, one-bath vacation rental located on the east side of the Sunshine on Siesta property. Designed for small families or couples, this inviting retreat offers private beach access and a peaceful island setting just moments from the sand.brbrSunrise places guests close to Siesta Key Village, where local restaurants, shops, and island attractions are all within easy reach, creating a convenient and relaxing home base for your stay.brbrHighlightsbr• Private beach accessbr• 2 Bedrooms / 1 Bathroombr• 1 King bed and 2 Twin bedsbr• Recently refreshed homebr• Shared pool with neighboring condominiumbr• Beach chairs and beach cartbr• Shared laundry br• Pets allowed with host approval br• Shared firepitbr• 1 Parking Spotbr• Convenient Siesta Key location near dining and shoppingbrbrGuests at Sunrise enjoy access to shared amenities that enhance the Siesta Key experience. The shared pool is a short two-minute walk away at the Calini Beach Club, which also offers private beach access approximately five minutes from the home. A centrally located shared laundry area is positioned between the duplex units. The shared backyard features a BBQ grill and a firepit seating area, creating a welcoming outdoor space to relax.brbrThe living area is welcoming and comfortable, offering a cozy space to unwind after a day outdoors. The kitchen is designed for simple meal preparation, allowing guests to enjoy breakfasts at home or relaxed dinners before heading out for evening activities.brbrThe primary bedroom features a king bed and a calm, coastal atmosphere that promotes restful nights. The second bedroom includes two twin beds, ideal for children or additional guests. The bathroom features a walk-in shower and is easily accessible from both bedrooms.brbrRoom Detailsbr• Primary Bedroom: King bedbr• Second Bedroom: Two twin bedsbr• Bathroom: Walk-in showerbrbrSunrise by Siesta Key Luxury Rental Properties offers a comfortable and well located retreat with private beach access and shared pool amenities. Whether you are planning a quiet getaway or an island adventure, this home is ready to welcome you. Book your stay today and enjoy the best of Siesta Key living.brbrTraveling with a larger group Reserve both Sunrise and Sunset together as Sunshine on Siesta – the Super Unit, giving your group more space and a seamless stay.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith 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. brbr1 car 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. brbrWe 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 see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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.

Sunrise - Perfect Couples Retreat!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$390.42

Experience coastal living at its finest in this 3-bedroom, 2-bathroom second-floor lakefront condo located in the desirable Gulf and Bay Club Bayside community in Siesta Key. Professionally managed by Gulf Coast Vacation Rentals, with breathtaking views of the lake, pool, and tennis court from the screened-in lanai, this home is a perfect retreat. The kitchen is equipped with stainless-steel appliances, and the adjacent dining table offers a great space for enjoying meals with family or friends. The light and bright living room enhances the relaxed, coastal vibe.brOn the first floor, the primary bedroom boasts a king-size bed and an attached bathroom featuring a walk-in shower with stunning marble from floor to ceiling. Upstairs, the second bedroom offers a spacious retreat with a queen-size bed, ideal for unwinding after a day of adventure. The second bathroom includes a dual vanity and a walk-in shower, while the third bedroom has two twin-size beds, perfect for guests or family members. For beach days, you'll find all the essentials stored in the garage, making this condo a true beach lover's paradise!brbrUpon arrival at Gulf & Bay Club Bayside, you'll be captivated by the beauty, serenity, and charm of this Key West style village. Stroll along the community path to the fishing dock, where you can take in the breathtaking views of the Intracoastal Waterway. Here, you might catch a fish, spot jumping dolphins, or even see a manatee.brbrOur spacious units, individually owned and decorated, are surrounded by lush, tropical landscaping, shell paths, and tranquil lakes with soothing fountains. Gulf and Bay Club Bayside offers a variety of on-site activities, including two heated pools, two tennis courts that can be converted to pickle-ball courts, and an exercise room. BBQ grills are also available for all guests to use, making it easy to enjoy a meal outdoors.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

Lakefront Siesta Key Condo With Beach Access - GBB 1206

Siesta Key, Florida, United States

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$502.73

This ground floor 2 bedroom, 2 bathroom unit is nicely updated and comfortably furnished with easy access to the pool and the beach. Our Property is managed by the Siesta Dunes Rental Office and the staff is available to assist you during your stay.brbrAmenities include:brbrGulf View, from 1st FloorbrbrKing in Master BedroombrbrShower in Master Bathroombrbr2 Twins in Guest BedroombrbrShower/Tub in Guest BathroombrbrTile Flooring ThroughoutbrbrDVD, Stereo and CD Playerbrbr3 Flat Screen TelevisionsbrbrWireless Internet Access

New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104

Siesta Key, Florida, United States

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$1064.98

Residence 501: - Direct Beachfront Water ViewbrbrThis stunning beachfront corner residence offers a truly unmatched vacation experience. Surrounded with an oversized, wraparound terrace and floor to ceiling windows, this 3-bedroom, 3-bathroom residence offers views for days. Decorator-designed with contemporary pieces and natural accents that perfectly complement the stunning panorama, the open floor plan features a spacious dining and living area that open onto the gulf-front terrace. The fully outfitted chef’s kitchen boasts top-of-the-line appliances complete with ice machine and wine fridge. The water views continue from the master suite with king bed, walk-in closet and spacious master bath with double sinks, private toilet, and walk-in shower. The residence has two additional bedrooms, one with ensuite bathroom and queen bed, and one with twin beds that can be placed together or apart to accommodate your needs. Immerse yourself in island luxury surrounded by sand, sea and sky in this stunning vacation rental. brbrBedding and Televisions:brMaster Bedroom: King Bed, TVbrBedroom 2: Queen Bed, TVbrBedroom 3: 2 Twin Beds or King Bed, TVbrLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Ice machinebr• Washer/Dryerbr• Clothing Steamerbr• Hairdryersbr• Private Wraparound Beachfront TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Breathtaking Gulf Views on Siesta: Residence 501

Siesta Key, Florida, United States

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$532.51

Residence 308 - Island ViewbrbrImagine your family and friends tucked away in this cozy coastal vacation rental. Tastefully decorated to reflect the natural beauty of the beach and island, this residence doesn’t miss an opportunity to pamper with the most luxurious appointments, fully outfitted gourmet kitchen, open floor plan, and private terrace. Located Island-side on the third floor, this residence offers beautiful sunrise and island views from the living area and master suite. The master bedroom boasts a king bed, walk-in closet, and spa-like bath, while the second bedroom is ideally suited for a family getaway with 2 twin-over-queen built-in bunk beds: allowing sleeping areas for up to six, with an ensuite bathroom. Thoughtfully designed to meet your individual needs while surrounding you in luxury, this vacation rental is the perfect place to relax, unwind and enjoy your next getaway. brbrBedding and Televisions:brMaster Bedroom: King Bed, TVbrBedroom 2: 2 twin-over-queen bunk beds brLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Private Beachfront TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

The Perfect Spot For you Family's Dream Beach Vacation: Residence 308

Siesta Key, Florida, United States

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Sleeps

$899.86

Residence 502 - Partial Water ViewbrbrThis beautifully appointed residence is one of the very few in the building offering four bedrooms to meet all your needs for the perfect island vacation. Thoughtfully laid out and professionally decorated, this residence truly has it all. The open floor plan features a fully equipped gourmet kitchen, dining area, and light-filled living area featuring floor to ceiling windows that open onto an oversized terrace. The outdoor living space offers south views of the beach and island, showcasing all of Siesta Key’s charm, while the four bedrooms overlook lush island greenery and afford island sunrise views. The master suite features a king bed, walk-in closet, and spa-like master bath. All four bedrooms delight with island views. Spacious in size and scope, this rental is the perfect beach vacation spot for your family and friends.brbrBedding and Televisions:brMaster Bedroom: King Bed, TVbrBedroom 2: King Bed, TVbrBedroom 3: King Bed, TVbrBedroom 4: Queen Bed, TVbrLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Hairdryersbr• Private Gulf View TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Spacious Fifth Floor Luxury Rental with Oversized Terrace: Residence 502

Siesta Key, Florida, United States

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$629.26

Residence 406 - Island ViewbrbrThis fourth floor, 3-bedroom, 3-bathroom residence offers the ideal location for your next island escape. Tastefully furnished in shades of blue and white, highlighted with rich natural wood pieces, this stunning vacation rental embodies coastal style. The open floor plan boasts spacious living and dining areas anchored by a gourmet kitchen designed for entertaining - with top-of-the-line appliances, dramatic quartz countertops and wine fridge. A private terrace off of the living area is the perfect place to take in island views and stunning sunrises. The master suite with king bed features a walk-in closet and spacious master bath with twin sinks, private toilet, and walk-in shower. The residence offers two additional queen bedrooms with baths, one ensuite and the other adjacent. Located Island-side on the fourth floor, this is the perfect beach retreat for you and your family and friends. brbrBedding and Televisions:brMaster Bedroom: King Bed, TV brBedroom 2: Queen Bed, TVbrBedroom 3: Queen Bed, TVbrLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Private TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Beautiful Coastal Getaway with Sunrise Views: Residence 406

Siesta Key, Florida, United States

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Sleeps

$545.24

Residence 404 - Island ViewbrbrOne of the few 2-bedroom, 2-1/2-bath units available to rent in this spectacular new beach front condo, Ten35 Seaside. Unit 404 proves that big things come in small packages. Located island-side on the fourth floor, this modern coastal unit decorator-designed space effortlessly blends fine textiles with natural elements for an undoubtedly modern coastal feel. The open floor plan boasts light-filled living and dining areas and offers island views and sunrise vistas from floor-to-ceiling windows of your very own private, covered terrace. Crescent beach is located just south of the world-famous Siesta Key Beach but shares that amazing turquoise water as well as the quartz sand that has been called the “finest, whitest sand beach in the world.” The chef’s kitchen features quartz countertops, top-of-the-line appliances and a dramatic kitchen island- ideal for gathering around with family and friends. The master bedroom offers a king bed with island views as well as a large walk-in closet and spacious master bath with twin sinks, private toilet, and walk-in shower. The residence offers one additional bedroom with a king bed and its own private bath. One additional ½ bath is available in the common area. This beautiful island retreat is the perfect place for your next vacation. brbrBedding and Televisions:brMaster Bedroom- 1 King, TVbrGuest Bedroom- 1 King, TVbrLiving Room- TV brbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TVsbr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top & Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Hairdryersbr• Private TerracebrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Beachfront Condo with Island Views: Residence 404

Siesta Key, Florida, United States

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$922.04

Residence 403 - Direct Beachfront Water ViewbrbrElegant design meets unmatched natural beauty in the gorgeous three-bedroom, three-bath condominium located beachfront on the fourth floor. The open floor plan features a fully equipped chef’s kitchen with top-of-the-line appliances and large quartz-topped island, leading into a spacious living and dining area. Past soaring floor-to-ceiling windows you’ll find your private, covered beachfront terrace – the perfect place to enjoy balmy Gulf breezes. The generous master suite is also located beach-front and offers incredible Gulf views from the moment you awake, with king bed, walk-in closet and spa-like bathroom with twin sinks and large walk-in shower. Two additional bedrooms, both and ensuite bathrooms round out the residence. Relax beachside and toast our famous Siesta Key sunsets on your next vacation in this lovely vacation rental residence. brbrBedding and Televisions:brMaster Bedroom: King Bed, TVbrBedroom 2: King BedbrBedroom 3: Queen BedbrLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Hairdryersbr• Private Beachfront TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Coastal Contemporary Residence with Spectacular Gulf Views: Residence 403

Siesta Key, Florida, United States

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$667.3

Residence 310 - Water ViewbrbrRelax in pampered comfort in this beautifully appointed 3-bedroom, 2-and-a-half-bath vacation rental. Located on the third floor, this corner residence faces northeast, yet boasts a thoughtfully placed terrace with expansive views looking north up world-renowned Siesta Beach. Tastefully furnished in modern beach chic, this residence’s open floor plan features a fully-outfitted chef’s kitchen with top-of-the-line appliances opening onto a a light-filled living and dining area. The living area opens onto the private terrace, sharing its views up the beach. The spacious master suite features a walk-in-closet and spa-like master bath. The residence offers two additional bedrooms, one with ensuite bath, and all three bedrooms provide lush island views. From sunrise to sunset, you will truly enjoy every moment of your vacation in this elegant residence. brbrBedding and Televisions:brMaster Bedroom: King Bed, TVbrBedroom 2: King Bed, TVbrBedroom 3: Queen Bed, TVbrLiving Room: TVbrbrResidence Amenities:br• Cablebr• Wifibr• Flat-Screen TV in living areabr• Sub-Zero Refrigeratorbr• Wolf Oven, Range-top and Microwavebr• Asko Dishwasherbr• Sub-Zero Wine Refrigeratorbr• Washer/Dryerbr• Clothing Steamerbr• Hairdryersbr• Private Gulf-View TerracebrbrProperty Amenities:br• Full-service Lobbybr• On-site Conciergebr• Linen & Housekeeping Servicesbr• Beach Valetbr• Beachfront Watersportsbr• Private, Under-building Parkingbr• EV Charging Stationsbr• Fitness Roombr• Gulf-front Fire Pitbr• Beachfront Grillsbr• Saltwater Pool & Spabr• 2nd Floor Beachfront Entertainment Terracebr• Poolside Cabanas

Gorgeous Third Floor Luxury Residence with Beach Views: Residence 310

Siesta Key, Florida, United States

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