Vacation Home Rentals By Owner In Siesta Key, FL

Aloha Kai #60 br brA Siesta Key Beachside Bliss Awaits! br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #60. This charming beach 1-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. Carefully crafted 1-bedroom retreat with in suite laundry, and boasting a welcoming front patio, providing a bright and cheerful area to unwind after a sunny day, Aloha Kai #60 encourages you to slip off your sandals, enjoy morning coffee on your private sunroom, and embrace a journey of relaxation and excitement. Here's what makes this home so special: brbrBedding Arrangement: br1 Bedroom: brMaster Bedroom with King-size bed, Smart TV brAdditional Sleep: 1 Sleep SofabrTop Features: brSleeps 4 brLargest 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. Direct 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 Patio: Sip coffee in the mornings or curl up with a good book in the enclosed sunroom. 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 #60 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 #60 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: br10% 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.

Plunge into Joy & Sun at Siesta Key Coastal Gem - Aloha Kai #60

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$661.98

Casa TranquillabrSpacious luxury home, 100% private, just 100ft from best views on Siesta Key. Impeccable 2025 remodel and array of amenities and features ensure a comfortable island getaway. Great for families with plenty of space onsite, three dining areas, large bedrooms, two patios, and easy access to beaches dining and entertainment! Just 100 feet to water-views, 5-minute walk to the Siesta Village, and 15-minute walk to top beaches. Book Casa Tranquilla today! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabr brbrWhat Guests Lovebr∙ Nearby Views – 100ft to the best views on the island and world-class fishingbr∙ The Village – 5-min walk to shopping dining and entertainment of Siesta Villagebr∙ Beaches – 15-min walk to Siesta Key's best beachesbr∙ Relaxing – two private patios and spacious interiorsbr∙ Sunsets – 100ft walk to best sunsets in America & 180-degree water viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ Activities – bikes, paddleboards, scooter and golf cart rentals nearby br∙ Island Trolleys – take them from the village, free of charge, up and down the islandbr∙ The Memories – walk to all siesta key is top attractions and guaranteed fun for allbrbrThe BeachbrYour nearest beach is a pleasant 15-minute walk on Ocean Blvd through the shopping and dining of the village. We like to walk to breakfast in the village then head straight to the beach at Access 7 or Sunset Pier. Leaving the beach, we stop off for lunch, dinner or happy hour. The beaches here are the widest, have panoramic views of the gulf to the North-West-and-South, and are the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. br*Special note - Siesta Key Access 4 is just 100 feet from the house and, although not a swimming spot, it delivers the best views on the island, and is an amazing pick for morning coffee, evening drinks, and sunsets on the water. It's also pet friendly, boasts world class fishing, and you could get picked up here by a hired tour boat.brbrbrThe HomebrLarge 3BR home fully remodeled in 2025. Impeccable décor and amenities throughout. Out-door grilling and dining, open floor plan perfect for bigger groups, surrounded by palms. Set on the Northern edge of Siesta Village just 5-min walk to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom DetailsbrIt's a large 3BR and all ground floor. This home has two king bedrooms, and a queen bedroom with additional twin over twin bunk bed, and a sofa in the living room and master. You can sleep up to 10 people. If you need more space, we can get you Tempur-pedic rollaways or an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location. brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key

Siesta Key, Florida, United States

3

Bed

3

Bath

10

Sleeps

$1054.57

The Big Dipper by Siesta Key Luxury Rental Properties brVacation Rental License #VR24-00291 brMinimum stay duration of 7 days/nights brbrWelcome to The Big Dipper, your ultimate Siesta Key vacation rental. This stunning canal front home offers four spacious bedrooms, a private bonus room with a queen bed and Jack-and-Jill bathroom, and three and a half bathrooms, making it an ideal retreat for families or groups. Just a short 3-minute drive to Siesta Beach, this inviting property blends comfort, space, and island convenience for a memorable coastal getaway.brbrHighlights br• Canal front home with serene views br• 4 Bedroom / 3.5 Bath br• 2 Kings, 3 Queensbr• Private fishing dock (no boat use available) br• Pool with in-ground spa br• 3-minute drive to Siesta Beach br• Screened-in balcony br• Whole-home purified, filtered water systembr• Outdoor kitchen br• Washer and dryer br• 4 Parking spaces br brOutdoor enthusiasts will appreciate the private fishing dock, where you can cast your line and enjoy tranquil canal views. Take a refreshing dip in the in-ground pool or unwind in the inviting spa. Gather with friends and family on the screened-in lanai or fire up the outdoor kitchen for unforgettable dining experiences. br brInside, The Big Dipper boasts an inviting living space with ample seating, ideal for spending quality time with loved ones. The fully equipped kitchen features modern appliances, including a wine fridge and a spacious island that makes meal prep a pleasure, plus an ice maker on the counter. A formal dining room down the hall sets the stage for memorable family meals, while the upstairs den, updated with a new 65in TV, provides a cozy retreat for younger guests to hang out and play. br brThe thoughtfully designed bedrooms create a peaceful sanctuary for everyone in your group, ensuring comfort and tranquility during your stay. The primary bedroom provides a king bed and an ensuite bathroom with a jetted tub and walk-in shower. Two additional bedrooms include two queen beds. The final two bedrooms include a king bed and a queen bed, adjoined by a jack-n-jill style bathroom with a walk-in shower. Each bedroom is furnished to provide generous sleeping arrangements while the half bath provides convenience to make this home ideal for families and groups. brbrRoom Details br• Primary Bedroom: King bed with ensuite bathroom featuring a jetted tub and walk-in shower br• Second Bedroom: King bed with jack-n-jill bathroom and walk-in shower br• Third Bedroom: Queen bed br• Fourth Bedroom: Queen bed br• Bonus Room: Queen bed with jack-n-jill bathroom and walk-in shower br brBook your perfect Siesta Key escape at The Big Dipper today! Create unforgettable memories in this beautiful setting, where comfort meets adventure just minutes from the beach! br brbr- brThis 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. brbrThis property does not allow pets of any kind. brbrThis property has an active Ring doorbell and additional video surveillance on the driveway and boat dock. brbrThe garage and fire pit are for the owner's use only. brbr4 cars maximum are able to park at this home’s driveway. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. 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. brbrIn accordance with the City of Sarasota's Rental Ordinance, this property requires a minimum rental period of 7 nights. The maximum occupancy for this home is 10 adults; however, children under 6 years of age are not included in the City’s occupancy limit. Siesta Key Luxury Rental Properties enforces a total occupancy limit of 10 persons, including both adults and children under 6. Should you have any questions regarding the City’s occupancy restrictions, alternative homes without such restrictions, or details about our rates, amenities, or policies, please feel free to reach out.

Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock

Siesta Key, Florida, United States

Bed

Bath

10

Sleeps

$937.31

Escape to your private paradise in one of the few single-family homes situated directly on the powdery white sands of Siesta Key. Your front yard is the beach, and the Gulf of Mexico is just steps from your door. This is the beachfront getaway you've been dreaming of.brbrThis spacious 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort and location. Forget the hassle of crowded elevators and long walks to the shore. Here, you can wake up to the sound of gentle waves and enjoy breathtaking sunsets from the comfort of your own home.brbrKey Features of Your Stay:brUnbeatable Location: A rare single-family home right on the world-famous Siesta Key beach.brbrAmple Space: Three comfortable bedrooms and 2.5 bathrooms provide plenty of room for family and friends.brbrConvenience: A private 2-car garage makes parking simple and secure.brbrWalkable Village Life: Stroll to the vibrant Siesta Key Village to explore a fantastic selection of restaurants, unique shops, lively bars, and local entertainment.brbrSpend your days soaking up the sun, building sandcastles, and swimming in the turquoise waters. In the evening, enjoy the easy walk to the village for dinner and live music. Everything you need for an unforgettable vacation is right at your fingertips.brbrDon't miss the chance to experience true beachfront living. Book your stay in paradise today!brbr*Please take a look at all of our beachfront properties available for rent below: brbrManasota Key 6 Direct Private Beachfront Condo UnitsbrVrbobr2404816brVrbobr2434823brVrbobr2434826brVrbobr2434830brVrbobr2434831brVrbobr2434832brbrManasota Key 5 Direct Private Beachfront Condo Units and 1 Single Family HomebrVrbobr2434844brVrbobr2434848brVrbobr2434850brVrbobr2434851brVrbobr2434852brVrbobr2435849brbrManasota Key Private Beachfront Single Family HomesbrVrbobr2434838brVrbobr2628248brVrbobr2628544brVrbobr2628321brbrManasota Key Private Beachfront CondosbrVrbobr2434835brVrbobr2434833brbrCasey Key Private Beachfront CottagesbrVrbobr2948793brVrbobr2948863brbrSiesta Key Beachfront Single Family HomebrVrbobr2434839brbrIndian Rocks BeachbrVrbobr2785311brbrClearwater BeachbrVrbobr1127221brVrbobr135915

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$513.82

This stunning home offers all the amenities you need for your most memorable Siesta Key vacation! Our private home offers an unbeatable location a short walk away from world famous Siesta Key Beach, voted the # 1 beach in the USA and Siesta Village! This home is ideal for families and small groups!brbrThe Casa on Siesta Key sits within walking distance to multiple beach access points that lead directly to the powdery sands of Siesta Key Beach.brbrThe Casa on Siesta Key - at 2,000 square feet of living space has plenty of room for up to six adults and eight total guests to spread out and enjoy the island lifestyle that the home fosters. The home welcomes you indoors with an open kitchen and dining area that's the perfect spot to relax before heading out back to the enclosed pool area situated directly on the canal after a long day at the beach.brbrThe home is a split floor plan with the master suite and one guest room on the south side of the home and the other bedroom on the north side of the home. The kitchen comes complete with stainless steel appliances and an eat-in island and dining room to provide ample seating. The luxury living room is equipped with plenty of seating. The private pool can be accessed through the towering sliding glass doors with the view of the canal just beyond. brbrOne highlight of The Casa on Siesta Key is the true master bedroom with a full ensuite and separate outside entrance. The king-sized bed and walk in shower are guaranteed to become a refuge for relaxation. Sunshine will pour in through the wall-lining windows to rejuvenate and refresh your senses.brbrbrThe backyard of The Casa on Siesta Key is an oasis in and of itself. With over 1800 square in the enclosed area, canal views abound from the rear of the home while using the salt water pool. Paved patio and access to the grill and outdoor eating area are additional enhancements. This is the perfect spot to relax and unwind after spending a day in the white powder sand of Siesta Key.brbrExclusive Amenities Include:brbr• Short Walk to Siesta Key Villagebrbr• Short Walk to Siesta Key Beachbrbr• Outdoor Dining Areabrbr• 3 Bedroom, 2 Full Bathbrbr• 1 King Bed, 2 Queen Beds, sleeper sofa (Sleeps 8) with linens providedbrbr• Private Boat Dockbrbr• Private off street parkingbrbr• Outdoor Dining Areabrbr• Free WiFi & HDTV'sbrbr• Coffee Maker, Washer & Dryer, and Kitchen Essentials Providedbrbr• Beach Towels, Chairs, Cooler, & Caddy Providedbrbr• Gas Grillbrbr• Enhanced cleaning protocols providedbrbr• Island Shuttle Transportation AvailablebrbrThe Casa can accommodate up to 8 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps: 2brbr• Bedroom # 2: Queen Bed (1) - Sleeps: 2brbr• Bedroom # 3: Queen Bed (1) - Sleeps: 2brbr• Common Space: Sofa Bed - Sleeps 2brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol with our Clean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!

SIESTA KEY-Single family home completely updated with in ground pool and cage.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$650.81

Recently Renovated and a Prime Location: Your Gateway to Siesta Key's Beauty & AdventurebrbrPerfectly positioned just north of Siesta Key Village, Waters Edge is only minutes away from the island's world-famous Siesta Key Beach, known for its powdery white sand and crystalline waters. Explore the vibrant village, with its eclectic mix of shops, delicious dining spots, and lively entertainment. Whether you're looking to soak up the sun on the beach, stroll through the village, or enjoy a quiet day by the canal, this home offers the perfect balance of convenience and peace.brbrLuxurious Accommodations: Comfort & Privacy for AllbrInside, Waters Edge provides a thoughtfully designed floor plan with three beautifully appointed bedrooms, ensuring comfort and privacy for everyone in your group.brbrMaster Suite: A tranquil retreat, featuring a king-sized bed, a cozy seating area, and direct access to the lanai. The master en suite is a spa-like haven with an oversized double shower, twin basin vanity, and a private commode, offering ultimate in comfort and relaxation.brbrSecond Bedroom: Ideal for couples or additional guests, this room also features a king-sized bed and en suite bathroom. It has direct access to the screened pool area, offering a seamless indoor-outdoor experience.brbrThird Bedroom: Perfect for families or friends, this room boasts double queen beds and easy access to the hall full bath, ensuring ample space and convenience for everyone.brbrWith three full bathrooms, the home ensures no shortage of convenience, making it the ideal choice for groups who want both comfort and privacy. The inviting living area is designed with relaxation in mind, featuring plenty of seating to unwind after a day of adventure. The fully equipped gourmet kitchen - a chef's dream! The large kitchen and dining area make it easy to prepare and enjoy meals together.brbrExceptional Outdoor Living: Your Private Canal-Front ParadisebrWaters Edge truly shines with its exceptional outdoor spaces. Step outside and relax in the screened-in private heated pool, perfect for swimming year-round, or enjoy a peaceful moment in the canal-front seating area overlooking the water. For added fun, the shuffleboard will provide hours of friendly competition for guests of all ages.brbrEnjoy a casual BBQ in the backyard, where the ambiance is perfect for creating lasting memories under the stars.brbrCanal-Front Location: With easy access to the Intracoastal Waterway, you'll have endless opportunities for kayaking, paddleboarding, and simply soaking in the serenity of the water. The canal's calm waters and peaceful atmosphere will make your stay extra special.brbrIdeal for Long-Term Stays: Comfort & Convenience AwaitbrWhether you're here for a short vacation or an extended stay, Waters Edge is the perfect place to experience Siesta Key. The home's spacious accommodations, quiet neighborhood, and convenient access to local attractions make it ideal for long-term guests who want to enjoy both privacy and proximity to the best of the island.brbrBook Your Siesta Key Getaway TodaybrExperience Waters Edge—where comfort, luxury, and relaxation come together in a stunning canal-front setting. Whether you're here to unwind by the pool, explore the natural beauty of Siesta Key, or spend time with loved ones, this home promises an unforgettable vacation.brbrBook your stay today at Waters Edge, and start planning your dream Siesta Key escape!brbrbrExclusive Amenities Include:br• Screened-In Private Heated Pool: Enjoy year-round relaxation.br• BBQ Grill: Perfect for outdoor cookouts and gatherings.br• Canal-Front Location: Beautiful views with access to the Intracoastal Waterway.br• Shuffleboard: Great for all ages to enjoy.br• 3 Bedrooms, 3 Bathrooms: Comfortably sleeps up to 8 guests.br• 2 King Beds, 2 Queen Beds, br• Close to Siesta Key Village and Beach: Easy access to dining, shopping, and the beach.br• Spacious Living and Dining Areas: Perfect for family meals and relaxation.br• 10 Minute Walk to Siesta Key Villagebr• 1 mile from Siesta Key Beachbr• Covered Back Patiobr• Private 2 Car Garagebr• Outdoor Dining & Lounge areabr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Free WiFibr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation Availablebr• Dog-Friendly with an additional Fee (1 dog up to 25lbs)brbrWaters Edge can accommodate up to 8 guests with a bedding configuration as follows:brbr● Bedroom # 1: King Bed (1) – Sleeps: 2br● Bedroom # 2: King Bed (1) – Sleeps: 2br● Bedroom # 3: Queen Beds (2) – Sleeps: 4brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!brbrPLEASE NOTE: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information.brReservation must follow under the accordance of the Sarasota County code regulations. This pool is heated from November 15th to April 15th.

Waters Edge | Canal-Front, Heated Pool, Walk to Siesta Key Beach & Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$418.27

This luxury townhouse features 2 Bedrooms and 2.5 Bathrooms, comfortably sleeping up to 4 guests! For your convenience, there is a beautiful kitchen, a large laundry room with a full-size washer and dryer, and plenty of space to relax by the pool on your island vacation! Located just one block from our world-famous, beautiful Siesta Key Beach, this home is in the best location for a relaxing vacation. Guests can enjoy beautiful sunset views from their balconies, take a swim in the shared outdoor pool, or take a walk into the village where all the shops and amazing restaurants are located! br*There is no garage parking.br*This property is stairs only. All guests must have the ability to use stairs.brbrBedroom 1: KingbrBedroom 2: KingbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*Security authorization Hold taken upon check-in. Amount: $1,500

Beautiful 2 bedroom Townhome with Stunning Views!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$653.72

Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Villagebrbr Why You'll Love This HomebrBali Hai House places you on a quiet canal in Siesta Key, offering private waterfront views while remaining close to the island's most popular spots. Located less than 1 mile to Siesta Key Village and under 1.5 miles to Siesta Key Public Beach Access 2, this three-bedroom retreat balances convenience with a peaceful residential setting. With a screened-in patio, private heated pool, and direct canal access, the outdoor spaces are designed for spending time together while staying connected to the water.brbr ‍ ‍ Perfect ForbrFamilies and small groups seeking a waterfront Siesta Key stay with private pool access and proximity to both the beach and village dining.brbr ️ Imagine ThisbrStart the morning on the screened patio overlooking the canal as wildlife moves quietly across the water. Brew coffee in the kitchen and plan the day, whether that means heading to Siesta Key Beach for a morning swim or strolling through Siesta Key Village for breakfast and shopping. In the afternoon, return home to cool off in the private pool or stretch out in the hammock while others gather around the outdoor seating area. Cast a fishing line directly from the canal's edge or simply settle into a quiet moment by the water. As evening approaches, light the fire table and share laughs outdoors, or unwind inside in the comfortable living area before retreating to your private bedroom space.brbr Where You'll Sleepbr• Bedroom 1: King Bed – Sleeps 2br• Bedroom 2: King Bed – Sleeps 2br• Bedroom 3: King Bed – Sleeps 2br• Living Room: Queen Sleeper Sofa – Sleeps 2brbrAccommodates up to 8 guests.brbr Explore The Areabr• 0.8 Miles to Siesta Key Village - Dining, Boutiques, Coffee Shops, and Live Musicbr• 1.5 Miles to Siesta Key Beach - Wide Sand, Gulf Swimming, and Beach Accessbr• 3.6 Miles to Point of Rocks - Perfect for Snorkeling and Shellingbr• 5.0 Miles to Downtown Sarasota - Options for Restaurants, Shows, and Nightlife. brbr⌛ Don't WaitbrYour reservation includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean followed by a detailed 35-point inspection prior to arrival.brbr Need to KnowbrPer Sarasota ordinance, this property is limited to one rental per 30-day period. Reservations must comply with Sarasota County regulations. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures.

Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$796.61

This private vacation home blends comfort, style, and location. With 3 king-sized bedrooms, a private heated pool, and tropical landscaping, Barefoot Bungalow is among the finest Siesta Key rentals with pool for families or couples. Located just steps from the beach and close to the best restaurants, shops, and nightlife, this spacious, fully furnished villa sleeps up to 6 guests and offers everything you need for a peaceful island stay.

Private home with Heated pool 1 Block to beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$450.97

Your Perfect Family Beach Haven on Siesta Key:brDiscover the ultimate family getaway in this beautifully modernized beach house, thoughtfully designed to make your vacation effortless and memorable. Just one mile from world-famous Siesta Key Beach, this stunning home offers the perfect balance of relaxation and adventure for families seeking their dream beach escape.brbrIndoor Comfort Meets Outdoor Paradise:brbrStep into your private oasis featuring a heated, screened pool surrounded by a spectacular lanai – perfect for family dinners under the stars or lazy afternoons on comfortable chaise lounges. Fire up the BBQ while the kids splash in the pool, or gather at the bistro set for morning coffee and vacation planning.brbrComfortable, Modern Living:brbrInside, the home flows seamlessly between welcoming spaces designed for family time and relaxation. The contemporary living room features a 60 smart TV, while a separate cozy family room offers the perfect spot for board games or quiet reading. The heart of the home is the fully equipped, modern kitchen, complete with new appliances, a generous island, and comfortable counter seating – ideal for family meals and snack time.brbrAnd rest easy... every bedroom is a private retreat, featuring:brbrIndividual smart TVs for winding down in the evening brBlackout blinds for perfect vacation sleep-insbrUSB charging ports in wall outlets for everyone's devicesbrbrBeach ready with everything you need: brbr6 adult beach cruiser bikes for family adventuresbrComplete beach setup with chairs, cart, umbrella, and beach gamesbrBeach towels and an outdoor shower to rinse off the sand when you return home brbrPrime Location:brbr1-mile ride to Siesta Key Public Beach, where you will find the famous colorful life guard stations!br2-mile ride to Siesta Key Village's restaurants and shopsbrEasy access to local entertainment and live musicbrConvenient Frog Hop trolley service available to get around the island brbrWhether you're planning active beach days or poolside relaxation, this thoughtfully appointed home offers everything your family needs for the perfect Siesta Key vacation. Create lasting memories in this ideal blend of comfort, convenience, and coastal charm. Minimum 28-day rental to comply with local laws for residential area.

Beautiful beach house with heated pool, 1 mile to Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$839.43

Nestled in Siesta Key on Palm Island, this delightful house offers 3 bedrooms: 1 king bed, 1 queen bed, and 2 bunk beds. With 2 bathrooms featuring a bathtub and shower, guests can relax and unwind after a day of exploring. Heating and AC ensure a comfortable stay year-round. Enjoy your time in Siesta Key at our lovely house.

Beautiful 3 bedroom home with heated pool! Half a mile to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$484.39

When a beach getaway infused with luxury and style sounds like a refreshing change of pace, you'll find everything you need when you book Miramar for your next trip this way. Miramar is a welcoming 4-bedroom, 3.5-bath home away from home that can accommodate up to 11 guests at a time. Whether your plans bring you here with a group of friends in tow or you're excited to spend quality time with the entire family, booking a stay in Miramar keeps you close to area fun while making the most of comfort, luxury, and style along the way. This multi-level property provides seamless access to Siesta Key Beach and comes with the decorative details and modern amenities throughout the make a great stay absolutely unforgettable.brbrInterior AmenitiesbrbrHigh-end furnishings, space, and ample light are yours for the enjoying when you book a stay in Miramar. Every level of this stunning home enjoys open concept design elements paired with large windows and vaulted ceilings. The result is a home that offers up an enhanced sense of living space as well as maximum Florida light flow and a fantastic frame on the view at all times. Guests who stay here can move easily between levels using the home's built-in elevate that runs from the garage all the way to the upper-level master suite. brbrThe living room in Miramar is a wonderful place to kick back in style. Here, guest will find a plush sofa and two decorative armchairs settled in front of a large flat-screen television and brick-framed fireplace too. A wall of windows allows guests to savor the sight of surrounding tropical foliage while the modern area rug is a beautiful offset to the rustic chic wood ceiling panels overhead. brbrThis room opens up to the dining area and kitchen where a home-cooked meal can always be created on a whim. The kitchen features an inviting wrap around breakfast bar with seating options paired with modern appliances and custom cabinetry already stocked with cookware and utensils. When it's time to dine together, guests can gather around the large formal dining table fit for 8-guests. brbrGetting a good night's sleep in Miramar is simple. Guests will love that every bedroom offers up a space of peace and tranquility to enjoy. The master bedroom hosts a king bed and en suite bath complete with a walk-in shower. Two additional bedroom host queen beds while the fourth enjoys two twin beds which is ideal for those traveling with little ones in tow. brbrWhen sleep eludes you and you're looking for added fun during your stay instead, make sure to make time to check out the screen room and wet bar located on the 4th floor!brbrExterior FeaturesbrbrWhile a stay in Miramar puts you in a prime location for exploring your surroundings, this home also has plenty of outdoor fun to offer right on-site. Guests can enjoy access to the property's private pool during their stay as well as the outdoor kitchenette when an alfresco meal is a priority. The home is equipped with no less than three outdoor patios that offer up a space to savor the sights and indulge in the fresh air at a moment's notice.brbrBook Your Getaway TodaybrbrEnjoy every moment of your Siesta Key adventure and make sure you have the luxurious accommodations to match! Have questions Send us a message — we'd love to help you plan your stay!brbrMINIMUM STAY REQUIREMENTS: One week minimum reservation required. Saturday to Saturday in most cases.brbrOptional:brbrPool Heating: $25/night for less than 3 weeks or $15/night for 3 or more weeks.

Luxury Home w/ Heated Pool and Private Beach Access

Siesta Key, Florida, United States

Bed

3

Bath

11

Sleeps

$477.27

Sundown Sanctuary by Siesta Key Luxury Rental Properties brbrWelcome to Sundown Sanctuary, a refined four bedroom, three and a half bath Siesta Key luxury rental that blends iconic mid-century modern design with effortless coastal living. Set along Midnight Pass Road in a tranquil North Siesta Key neighborhood, this architecturally significant estate offers a private 30-foot lap pool with waterfall, a serene Zen garden, and a detached two bedroom guesthouse. Tucked beside a protected nature preserve and just an 18-minute walk to the Beach, the home is also minutes from Siesta Village, making it ideal for families, couples, and design-forward guests seeking privacy, space, and island-inspired comfort. Four on-site parking spaces are available. brbrHighlights br• 18-minute walk to the Beach br• 4 Bedrooms / 3.5 Bathrooms br• 1 King, 4 Queens, 1 Queen Murphy bed br• Private 30-foot lap pool with waterfall br• Separate two-bedroom guesthouse with full kitchen br• Private Zen garden with pond and sculpture br• Adjacent to a Sarasota County nature preserve br• Screened porch and multiple outdoor lounge areas br• Beach chairs and beach cart provided br• Washer and dryer br• Pet-friendly with approval br• 4 Parking spaces brbrDesigned for luxury coastal living, Sundown Sanctuary’s outdoor spaces set the tone for a restorative stay. The private lap pool, accented by a cascading waterfall, anchors the gated courtyard and invites morning swims or sunset relaxation. Surrounding lounge seating, a shaded hammock area, and sculptural elements create a peaceful tropical retreat. The Zen garden offers a quiet escape among palms and stone pathways, while the screened porch and outdoor seating areas provide comfortable spaces to gather throughout the day. brbrInside, the home celebrates its mid century heritage with airy, open concept living spaces, floor to ceiling windows, and curated art pieces that feel both elevated and inviting. The main living area features modern furnishings and a sleek fireplace, creating a comfortable setting for relaxing evenings. The main floor bar kitchen includes a small fridge, counterspace, and stovetop for quick meals and snacks. A spacious dining area flows seamlessly into the living room, making the layout ideal for entertaining or unwinding after a day at the beach. The second level of the main house includes the full kitchen, outfitted with granite countertops, stainless steel appliances, and ample workspace for preparing everything from quick breakfasts to shared family dinners. brbrThe main house features two thoughtfully styled bedrooms on the second level, with calming tones and Scandinavian inspired details. The primary bedroom offers a king bed and shares a full bathroom with a shower and tub combination. The second bedroom includes a queen bed and shares the same bath. A bonus room with a queen Murphy bed provides additional flexibility for guests. On the ground floor of the main house, a full bathroom with walk-in shower adds convenience. br brThe detached guesthouse is perfect for extended families or guests seeking added privacy. It includes two queen bedrooms connected by a Jack-and-Jill bathroom with walk-in shower, along with a full kitchen, cozy living area with fireplace, and a screened porch overlooking the courtyard. brbrRoom Details brMain House br• Primary Bedroom (Second Floor): King bed, shared bath with shower and tub br• Second Bedroom (Second Floor): Queen bed, shared bath br• Bonus Room: Queen Murphy bed br• Ground Floor: Full bathroom with walk-in shower brbrGuesthouse br• Bedroom 1: Queen bed br• Bedroom 2: Queen bed, Jack-and-Jill bath with walk-in shower brbrGuests will enjoy thoughtful conveniences including an outdoor shower, BBQ grill, private parking, beach chairs, and a beach cart. The home’s location near a nature preserve enhances the sense of serenity while still offering easy access to the beach and island attractions, making it well-suited for Siesta Key weekly rentals or extended stays. brbrExperience a truly unique Siesta Key vacation home with pool at Sundown Sanctuary, where mid-century architecture meets tropical tranquility. From the Zen garden and private guesthouse to the sun-drenched courtyard and elegant interiors, every detail is designed for relaxed island living. Book your stay with Siesta Key Luxury Rental Properties today and discover one of Siesta Key’s most distinctive coastal retreats! brbr- brThis home is managed by Siesta Key Luxury Rental Properties. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.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. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. 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.

Sundown Sanctuary! Modern home near the north end of Siesta Key!

Siesta Key, Florida, United States

5

Bed

Bath

10

Sleeps

$4029.54

Enjoy a peaceful stay at this marvelous 5-bedroom house in Siesta Key.brWe offer 5 bedrooms, 2 bathrooms, family room, full kitchen, laundry, patio, pool and free parking.brJust a few minutes walking to Siesta Key.brWe can accommodate up to 15 people.

Walk to siesta key

Siesta Key, Florida, United States

5

Bed

2

Bath

15

Sleeps

$674.79

Aloha Kai #34 & #55 (Combined Villas) br(Across the street from each other) br brA Siesta Key Beachside Bliss Awaits! br brStep into the tropical embrace of Aloha Kai #34 & #55, where the rhythmic charm of Siesta Key and a short stroll to Crescent Beach create a perfect escape. This combined villa duo transforms two homes into a seamless paradise, blending sunlit serenity with island adventure. Aloha Kai #34 & #55 invites you to shed your worries, sip coffee on your private patios, and dive into a world of relaxation—book your island haven today! Here's what makes this home so special:brbrBedding Arrangement: brbrAloha Kai #34: br1 Bedroom: brMaster Suite: Queen-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brAloha Kai #55: br1 Bedroom: brMaster Suite: King-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the living area brTop Features: brSleeps 8 brLargest Pools on Siesta Key: Plunge into the expansive, sparkling pools surrounded by large lounging decks with plenty of lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access Points: Just a short walk to the powdery white sands of Crescent Beach, rated #1 in the U.S., with shaded pavilions and lounge chairs for your comfort. brFront Patio/Sunroom: Sip morning coffee or unwind with a book in the bright, enclosed sunroom. brCommunity Amenity Sets: Enjoy shuffleboard, ping pong, and poolside community rooms, plus complimentary beach toys and floats for endless seaside fun. brPerfect Home Base Location: Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for island exploration, with activities for all ages and nature lovers. brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #34 & #55 offers easy access to Crescent Beach, famed for its dazzling quartz sand and emerald waters. Whether you're strolling the 3-mile shoreline, lounging under a shaded pavilion, or savoring breathtaking Gulf sunsets, this villa pair delivers tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be effortless and unforgettable. Book your Siesta Key escape at Aloha Kai #34 & #55 today! 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: br10% 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. Every Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$435.77

Located on the Voted number #1 beach in America famous Siesta Key in Sarasota, Florida, The Magnolia House offers the perfect vacation getaway. Two separate units are on this property at 317 and 319 Canal Rd, one upstairs and one downstairs. Each unit is booked separately, or you can book both units for a private family vacation. We book only weekly from Saturday to Saturday.brRecently renovated in the Tommy Bahama style, The Magnolia House maintains that great 'Old Florida' flair with all of the modern-day amenities our guests expect. brOnce you arrive, simply park the car and let the good life begin. Walk one block to Siesta Key Village for a fresh tropical drink at the Daiquiri Deck, or have some oysters at the Siesta Key Oyster Bar. Ready for the beach The Gulf is only steps away! Need some groceries or some new flip flops You guessed it. Nearby! Don't feel like going anywhere How about a dip in your heated pool brGuests at The Magnolia House have it all! brWe hope you will cherish your Siesta Key beach memories, which many have been made at The Magnolia House for over twenty years. We hope you will join us to create your own!br*A SIGNED CONTRACT IS REQUIRED TO CONFIRM. * EVERYONE MUST BE 25 YEARS OR OLDER OR ACCOMPANIED BY PARENTS, NO PETS ALLOWED, AND PLEASE NOTE PARKING IS LIMITED. Each unit has one off street covered parking spot.

SHORT WALK TO VILLAGE, BEACH - HEATED POOL - LUSH LANDSCAPING 2 SEPARATE UNITS.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$503.51

Enjoy a soothing stay at this 3-bedroom house in Siesta Key, a very short walking distance from the beach. The bedrooms feature a king, queen, and twin bed, ensuring a perfect night's sleep for all guests. With amenities like AC, WiFi, and a washing machine, your stay will be stress-free. The two bathrooms offer showers and hair dryers for added convenience. Relax in the peaceful living room with an extra queen bed.brWe look forward to welcoming you to our place.

Charming spacious 3-bedroom house walking minutes from Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$878.98

Brand new pool home! Enjoy this beautifully remodeled 3 bdrm/3bath home on Siesta key named the #1 Beach in the country! We are LESS THAN 1 minute to the powdered sugar sands and turquoise waters. All flooring, linens, dishes, appliances, furniture...everything is new, just out of the box. Upon entry, the two-story vaulted ceilings and open concept floorplan with extra-large windows provide ample in-direct lighting from every room. Relax by the brand new heated saltwater pool with lots of lounge chairs and fire pit! All bedroom windows have remote controlled window coverings available to your desired likeness with a touch of a button. The great room opens up to the no expense spared kitchen featuring brand new white, soft-closing cabinets finished with quartz countertops. The kitchen contains stainless-steel appliances paired with a retractable exhaust hood and recessed lighting which is both functional and aesthetically pleasing. That combined with a reverse osmosis water filtration system—is sure to please the most discriminating guest. Kitchen is finished off with a frosted glass panel door providing light and privacy to the interior laundry room with new appliances, cabinets & storage. Kitchen counters extend into the breakfast bar with panoramic views of the lush Florida native landscape. The main level offers open living, dining for six, and kitchen area with a big flat screen tv. After a day at the beach, relax and enjoy the super comfy 5-piece deep seating sectional! Flowing into the spacious dining room, sliding glass doors open onto a spacious outdoor deck ideal for sunsets and backdrop of Glebe Park. There is a brand-new outdoor Teak dining table for four and Weber grill for evening BBQ’s.brDown the hall is a full bath with shower/tub combo, brushed gold hardware, and crisp white herringbone tiles on the walls that showcase coastal modern floor tiles. The neighboring bedroom is a perfect guest room with queen bed with a large window and access to the rear deck. Leading upstairs both the window and cable railing keep an open airy feel. The second twin bedroom is equipped with vaulted ceilings and a large south-facing window bringing in the outdoors. The second bathroom was designed with a walk-in shower, custom-cut shower glass, an infinity drain, brushed gold hardware, and shiplap walls. The glazed modern blue/green shower tiles complement the window view, balancing modern finishes with nature once again. Once upstairs, there is a beautiful super-spacious master bedroom featuring a new canopy king poster bed and luxury linens! The master offers a vaulted ceiling and windows with a walk-in closet is big enough for any fashionista. The master bathroom is a true oasis. Double vanity sinks with fluted cabinets and brushed gold hardware, a coastal chic chandelier, and vaulted ceilings just to start. A stunning stand-alone tub with a tropical view showcases the mural tiled wall. Just behind, a separate walk-in oversized shower with crackle glazed tile and custom-cut shower glass wall & door.

Beautiful New Everything! Paradise on Siesta Key! Brand new pool home!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1556.03