Vacation Home Rentals By Owner In Siesta Key, FL

$473.96

Brand new rental! Paradise Palms: Heated Pool, Game Room, & Minutes to Siesta Key Beach!

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Paradise Palms, a freshly updated three-bedroom sanctuary where island peace meets modern comfort. Tucked away in a quiet residential pocket just minutes from the world-famous white sands of Siesta Key Beach, this home offers the perfect blend of privacy and proximity. Featuring a sparkling screened-in pool and two spacious living areas, it’s a premier choice for families or small groups looking to experience the best of the Gulf Coast. brbr brbrThe Highlights brbr- Private Screened-In Pool: Your own tropical oasis for sun-soaked afternoons. brbr- Prime Location: Less than 1.5 miles to Siesta Key Beach access. brbr- Recreation Ready: Ping pong and air hockey tables, plus board games, puzzles, and books. brbr- Beach Gear Included: We provide beach chairs and a beach cart to make your shore days effortless. brbr- Open-Concept Living: Two distinct living rooms with vaulted ceilings and skylights. brbr- Al Fresco Living: Screened lanai with BBQ grill, outdoor dining, and lounge seating. brbr brbrThe Living Space brbrThe interior of Paradise Palms is designed for relaxation. The bright, airy layout features two separate living rooms, offering plenty of space for the group to spread out. One living area serves as a cozy media room with a large flat-screen TV and direct pool access, while the second boasts soaring vaulted ceilings and coastal decor. Perfect for a quiet morning coffee or evening cocktails! brbr brbrThe fully equipped kitchen features modern appliances and bar seating for casual snacks. For family dinners, the formal dining area comfortably seats eight, ensuring everyone has a spot at the table. brbr brbrBedrooms & Bathrooms brbr- Primary Suite: A true retreat featuring a King bed, private sitting area, and an ensuite bathroom with a walk-in shower. Sliding glass doors lead you directly from your bedroom to the pool deck. brbr- Bedroom 2: Features a comfortable Queen bed and easy access to the hall bath. brbr- Bedroom 3: Perfect for kids or additional guests with a Full bed. brbr- Extra Sleeping: A Queen sleeper sofa in the living room provides flexibility for larger groups. brbr brbrOutdoor Oasis brbr- Step through the sliding doors into your private screened-in lanai. Surrounded by lush tropical landscaping, the pool area is designed for the Florida lifestyle. brbr- Fire up the BBQ grill for a poolside cookout, dine at the outdoor table, or challenge the family to a tournament on the ping pong and air hockey table. brbr brbrEssential Amenities brbr- High-Speed Wi-Fi & Smart TVs for streaming. brbr- Full-Sized Washer & Dryer inside the home. brbr- Parking: Space for up to 4 vehicles (No overnight street parking allowed). brbr- Pet Policy: We are dog-friendly with prior approval and fee! brbr brbrThe Neighborhood brbrParadise Palms is situated in a peaceful residential neighborhood. To maintain the tranquility of our community, we ask all guests to observe local noise ordinances and be respectful neighbors. You are just a short drive or bike ride away from the vibrant Siesta Key Village, local boutiques, and the breathtaking sunset views of the Gulf. brbr brbrOther information: brbr- No smoking property brbr- Pool heat extra - reach out for details. brbr- No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. brbr- Per Sarasota ordinance, this rental is limited to 1 rental per 30 day period. brbr brbrReady to soak up the sun Book your stay at Paradise Palms today!brbrAll 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.

3

Bed

2

Bath

8

Sleeps

$367.14

/ Nightly

Private Vacation Home

Luxury Private Condo on The Anchorage, Siesta Key Condo 1024

Siesta Key, Florida, United States

5 Star Villa Holidays is proud to present Siesta Key Condo 1024.brbr In quaint Siesta Key you’ll find gorgeous beaches, beautiful views and this amazing vacation home! Boasting 2 bedrooms and 2 bathrooms, this home is the quintessential property for anyone looking to escape reality. Beautiful 7th floor views are just a bonus!brbr To begin, the living room here flows in and outdoors when you open the sliding glass doors. You can enjoy the salty ocean air right from your own living room.brbr This space overflows into the patio where morning coffee can be enjoyed everyday as you watch the quiet ocean waves come in. The living room also flows into the fully stocked kitchen.brbr Stocked with the necessities of home, you’ll be able to whip up your favorite meals in no time. As you explore more into the home, you’ll run into both bedrooms on either side of the condo.brbr The master bedroom has a king bed, patio access, and an ensuite bathroom. The guest bedroom has 2 queen beds, each made for rest and relaxation.brbr No matter which you choose, you’ll find yourself rested and ready for a day at the beach.brbr You can’t forget to enjoy all the amenities that this property has to offer. Swim all day long at the pool and then try your hand at shuffleboard or tennis.brbr Enjoy the intracoastal walking trails where you can enjoy gorgeous views of the water. Book your stay today and let the sunshine of Siesta Key rejuvenate you today!

Bed

Bath

Sleeps

$1460.6

/ Nightly

Private Vacation Home

Perfect Location. Roof Top Deck. Gulf Views. Heated Pool/Spa w/ Rain Curtain

Siesta Key, Florida, United States

Blue Paradise by Siesta Key Luxury Rental Properties br brExperience the epitome of Siesta Key luxury at Blue Paradise, a stunning six-bedroom, six and a half-bath retreat perfectly situated just half a block from Siesta Key Beach and across the street from Siesta Key Village. With breathtaking tropical views, this resort-style home is designed to provide an exceptional vacation experience near the Siesta Key beach and village. Ideal for large families, groups, or extended stays, Blue Paradise offers the perfect blend of outdoor entertainment, spacious indoor living, and premium amenities. brbrHighlights br• 2-minute walk to Siesta Key Beach  br• 6 Bedroom / 6.5 Bath br• 5 Kings, 2 Full/ Full bunks br• Private pool and in-ground spa br• Putting green, Ping-pong table br• Rooftop deck br• Beach chairs provided br• Outdoor bar and dining area with BBQ grill br• 3-minute walk to Siesta Key Village for shopping and dining  br• 3 Parking spaces br brEnjoy your private outdoor paradise with a saltwater pool with a rain curtain, in-ground spa, and a 3-hole putting green, providing countless hours of fun and relaxation. The covered patio features a built in bar, cooler, and bar seating for enjoying drinks. Two flat-screen TV's and an oversized sectional with overhead fans complement the outdoor space, making it the perfect setting for gatherings. After a day in the sun at the beach or pool, rinse off in your own outdoor shower. br brThe open concept main living area features comfortable seating, a TV, and coastal decor, creating a welcoming environment. The kitchen’s high end appliances and ample countertop space cater to family and friends preparing meals together. The second floor offers an additional living area with a TV and wet bar, complete with a wine fridge and coffee maker, ideal for entertaining and relaxing in style. br brThe primary suite offers a king-sized bed, balcony access, and an ensuite bath with a walk-in shower for a spa like retreat. All five guest bedrooms are furnished with king-sized beds, each with bath access, either ensuite or shared, and balcony access, all decorated with a coastal elegance. The sixth bedroom features two full over full bunk beds and an ensuite with a shower and tub combo, offering space and comfort for kids or additional guests. Each bedroom creates a restful haven for a luxurious night’s sleep. brbrRoom Details br• Primary Bedroom: King bed, balcony access, ensuite with walk-in shower  br• Second Bedroom: King bed, balcony access, ensuite with walk-in shower  br• Third Bedroom: King bed, balcony access, ensuite with walk-in shower  br• Fourth Bedroom: King bed, balcony access, ensuite with walk-in shower  br• Fifth Bedroom: King bed, balcony access, ensuite with walk-in shower  br• Sixth Bedroom: Two full-over-full bunk beds, ensuite with shower/tub combobr brEnjoy access to ping pong, beach chairs, and an outdoor living space filled with amenities right at home. Located near the beach, shops, and dining, Blue Paradise offers endless opportunities for relaxation and adventure on Siesta Key. Whether enjoying time by the saltwater pool or exploring world-class beaches just minutes away, this home guarantees an unforgettable vacation.br brReserve your stay at Blue Paradise today and indulge in a luxurious, family friendly escape. From beach days to memorable evenings on the rooftop deck, this stunning home provides all you need for a lifetime of memories. Book now and start planning your perfect Siesta Key vacation! br brbr- brThis home is managed by Siesta Key Luxury Rental Properties. br brThere are No Pets Allowed on this property. brbr3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest.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.

6

Bed

6

Bath

18

Sleeps

$366.71

/ Nightly

Private Vacation Home

Rent the Perfect 2 Bedroom Condo on The Anchorage, Siesta Key Condo 1002

Siesta Key, Florida, United States

3

Bed

2

Bath

6

Sleeps

$1428.65

/ Nightly

Private Vacation Home

Luxury Siesta Key Retreat 4 Bedroom 4 Bathroom Pool Cabana Chef Kitchen

Siesta Key, Florida, United States

Luxury Siesta Key Resort Retreat with Pool CabanabrbrWelcome to your private luxury vacation rental in Siesta Key—a newly built 4,250 sq. ft. modern coastal retreat designed for unforgettable family vacations, beach getaways, and resort-style living. Just minutes from world-famous Siesta Key Beach, you'll enjoy the perfect combination of privacy, luxury, and convenience.brbrPrime Locationbrbr• 4-minute drive to Siesta Key Beachbr• 8-minute bike ride to the beachbr• Concierge bike rentals availablebr• Minutes from Siesta Key Village restaurants, bars, shopping, and entertainmentbr• Ample parking for multiple vehiclesbrbrResort-Style Outdoor LivingbrbrStep outside and experience one of the most impressive private outdoor spaces on Siesta Key. The property features over 4,100 sq. ft. of limestone patio and outdoor living space centered around a spectacular 1,100 sq. ft. saltwater pool with integrated spa, tanning ledge, and soothing water features.brbrOutdoor Featuresbrbr• Resort-style saltwater pool & spabr• 1,800 sq. ft. covered outdoor living areabr• Fully equipped outdoor kitchen with BBQ grill, hood vent, refrigerator, sink & ice makerbr• Comfortable outdoor lounge seating and dining areasbr• Poolside outdoor showerbr• Tropical landscaping throughout the propertybr• Outdoor fitness area with weight machine, rowing machine, yoga mats & wellness spacebr• Herb and vegetable gardens available for guest enjoymentbrbrFor peaceful mornings, stroll the tropical pathways that wrap around the property, perfect for meditation, yoga, or enjoying your morning coffee.brbrPrivate Pool CabanabrbrA standout feature of the property is the beautifully appointed pool cabana overlooking the resort-style pool and tropical grounds. The cabana provides guests with extra privacy and flexibility for group trips and families.brbrThe cabana includes:br• Private bedroom suitebr• Comfortable living roombr• Kitchenette - microwave and fridgebr• Full bathroom with walk-in showerbr• Dedicated work space with desk and chair br• Direct access to the pool and outdoor living areasbrbrPerfect for grandparents, extended family, or guests seeking additional privacy during their stay.brbrModern Luxury InteriorbrbrInside, you'll find soaring ceilings, designer finishes, and an open-concept layout designed for entertaining and relaxing.brbrChef's Kitchenbrbr• Premium Sub-Zero double fridgebr• Premium Wolf 6-burner gas range featuring a built-in flat top griddle, spacious convection oven, and additional companion oven for ultimate cooking flexibility.br• Stunning 18-foot honed Brazilian Dolomite waterfall islandbr• Seating for 6 at the islandbr• Two Bosch dishwashersbr• Filtered hot and cold water faucetbr• Pop-up charging stations with USB, 3-C, 3 prong compatibility br• Fully stocked with cookware, utensils, serving pieces, and kitchen essentialsbr•Mini drink fridge on the side of the islandbr•Blender, toaster, Instapot, slow cooker and premium rice cooker brbrLiving & Diningbrbr• 23-foot vaulted dining room ceiling with custom artisan chandelierbr• Dining table seating for 8br• Spacious living room with oversized seatingbr• Hidden pop-up televisionbr• Custom lighting throughout the homebr• Hurricane-rated triple-pane sliding glass doorsbr• Solid white oak interior doorsbr• Handcrafted Colorado Sapele Mahogany pivot entry doorbrbrAdditional Amenitiesbrbr• High-speed WiFi throughout the propertybr• Dedicated workspace areasbr• Coffee station and tea selectionbr• Two washers and two dryers available for guest usebr• Ceiling fans throughout the homebrbrBedrooms & BathroomsbrbrPrimary Suite (First Floor)brbrLuxurious king suite featuring garden views, custom walk-in closet, and spa-inspired ensuite bathroom with premium finishes and oversized shower.brbrPowder bathroom brLuxurious powder bathroom conveniently located between the kitchen and living room, featuring designer finishes and elegant details that provide both comfort and sophistication for guests.brbrBedroom 2 (Upstairs)brbrKing bedroom with walk-in closet and access to a large shared balcony overlooking the pool, tropical landscaping, and cabana below.brbrBedroom 3 (Upstairs)brbrTwo full-size beds with sliding glass doors opening to the shared balcony. Ideal for families and additional guests.brbrShared Upstairs BathroombrbrFull bathroom with shower and vanity conveniently located between the upstairs bedrooms.brbrThere is also a completely separate efficiency apartment located above the garage occupied by long-term tenants. The apartment has its own private entrance and is entirely independent from the main house, pool cabana, pool area, and guest amenities. Tenants do not have access to any guest spaces, ensuring privacy and an exclusive resort experience for vacation guests.

Bed

Bath

Sleeps

$382.11

/ Nightly

Private Vacation Home

Walk to #1 Beach in US-Family 3BDR Retreat

Siesta Key, Florida, United States

House of Siesta: our home by the coast. We’re opening our doors not to a regular rental but to our own home, created with love so guests can feel truly at home too. Just 0.7 miles from the #1 beach in the USA and minutes from Siesta Village, it’s spacious, welcoming, and perfect for two families to share. Enjoy open living, a cozy patio with grill, plus beach gear, bikes, toys, and games. A place to reboot, reconnect, and make unforgettable memories.

Bed

Bath

Sleeps

$618.34

/ Nightly

Private Vacation Home

Luxury Townhome with a Rooftop Deck! - Changing Channels

Siesta Key, Florida, United States

Changing Channels by Siesta Key Luxury Rental Properties br brWelcome to Changing Channels, your perfect vacation retreat, great for families and friends seeking relaxation and adventure in stunning Siesta Key! This beautiful multi-level home boasts four bedrooms, four bathrooms, and a shared heated pool. With its prime location just minutes from the beach, this property is designed to provide an unforgettable luxury experience. brbrHighlights br• 2-minute walk to Siesta Key Beach br• 4 Bedroom / 4 Bathroom br• 1 King, 4 Queen beds br• Shared heated poolbr• Gas grill br• Beach chairs br• Close proximity to vibrant Siesta Key Village br• Washer and dryer br• 2 Parking spaces br brUnwind at Changing Channels in the shared backyard oasis, where a luxurious pool is surrounded by ample lounge space perfect for soaking up the Florida sunshine. Enjoy a relaxed and comfortable setting, ideal for quiet afternoons poolside and making the most of Siesta Key’s beautiful weather.br brThe main living floor features a modern and inviting atmosphere, with a cozy seating area and a flat-screen TV, ideal for family gatherings. The exquisite dining room table provides a lovely space for shared meals, and the fully equipped kitchen, with top-of-the-line appliances and a large island, is sure to delight any chef. Step out onto your private deck for outdoor dining with a view. br brThe primary bedroom creates a serene escape, designed in warm, neutral tones with a king bed, comfortable seating area, and spacious walk-in closet. Its luxurious ensuite bathroom features dual vanities, a separate soaking tub, and a walk-in shower. The three guest bedrooms offer queen-sized beds, ample closet space, and ensuite bathrooms for added convenience and privacy. One guest room features rooftop access, complete with a wet bar and wine fridge, enhancing your entertainment options. brbrRoom Details br• Primary Bedroom: King bed and ensuite bathroom with soaking tub and walk-in shower br• Second Bedroom: Queen bed, ensuite bathroom with walk-in shower br• Third Bedroom: Queen bed, ensuite bathroom with walk-in shower br• Fourth Bedroom: Two queen beds, rooftop access, ensuite bathroom with shower/tub br brEnjoy the convenience of in home washer and dryer, an iron and ironing board, parking, and a serene, shared backyard perfect for relaxation and family fun.br brChanging Channels is your gateway to the ultimate Siesta Key experience, just steps away from pristine beaches and the lively Siesta Key Village. Book your stay with Siesta Key Luxury Rental Properties today and prepare for a memorable escape filled with sun, sand, and luxury! br brbr-brThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell surveilling the exterior public approach areas. brbrThis property does not allow pets of any kind. 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. brbrThis home is managed by Siesta Key Luxury Rental Properties. 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.

Bed

Bath

Sleeps

$832.74

/ Nightly

Private Vacation Home

Private Gated Home in Siesta Village, Heated Pool & Pool Table - The Hideaway

Siesta Key, Florida, United States

The Hideaway by Siesta Key Luxury Rental Properties brbrWelcome to The Hideaway, a luxurious private gated retreat featuring four bedrooms and five bathrooms, located less than a 5-minute walk to Siesta Key Beach. This beautifully designed home offers the perfect blend of upscale comfort and relaxed island living, complete with a screened in pool, spacious balconies, an elevator, and high-end finishes throughout. Just steps from Siesta Key Village, this property is ideal for family vacations and extended coastal getaways. brbrHighlights br• 3-minute walk to Siesta Key Beach br• 4 Bedrooms, 4.5 Bathrooms br• 1 King, 2 Queens, 2 Double over Double Bunk Beds br• Private Pool in Screened-In Patio br• Multiple Balconies br• Pool Table and Upstairs Game Room br• Elevator br• Near Siesta Key Village br• 4 Parking Spaces brbrThe centerpiece of this elegant home is the expansive screened in outdoor oasis, designed for both relaxation and entertainment. Guests can take a refreshing swim in the private pool, unwind on comfortable loungers, or enjoy meals outdoors with the serene sound of island breezes. The covered patio and screened in surroundings create a peaceful environment protected from sun and insects. Inside, the home’s luxurious features continue with a game room and bar area on the upper level. The elevator adds convenience for all ages, and the private gated entrance enhances the sense of seclusion and comfort. brbrThe open concept main living area offers a bright and welcoming setting, seamlessly connecting the living room, dining space, gourmet kitchen, laundry room, and half bath. The living room features a plush sofa and large TV for movie nights, while the modern coastal kitchen boasts high-end appliances and a gas stove designed for preparing meals with ease. Guests can dine casually at the kitchen island or more formally at the dining table. Upstairs, the game room includes a pool table and a stylish bar setup. Sliding glass doors open to a stunning deck with outdoor seating, creating a relaxing spot to enjoy the refreshing island air. brbrThe first floor primary bedroom is a serene retreat with a canopy king bed, patio access, pool views, and a luxurious ensuite bathroom featuring a rain shower, standalone soaking tub, and an oversized walk-in closet. On the second floor, two beautifully designed queen bedrooms each feature their own ensuite bathroom with walk-in showers, offering comfort and privacy for guests. The third-floor bedroom is perfect for younger travelers, with two double-over-double bunk beds, a workstation, closet, and a private ensuite bathroom with walk-in shower. brbrRoom Details br-Primary Bedroom (1st Floor): King bed, patio access, ensuite bathroom with walk-in rain shower and standalone tub br-Second Bedroom (2nd Floor): Queen bed, ensuite bathroom with walk-in shower br-Third Bedroom (2nd Floor): Queen bed, ensuite bathroom with walk-in shower br-Fourth Bedroom (3rd Floor): Two Double-over-Double Bunk Beds, ensuite bathroom with walk-in shower brbrThe Hideaway offers a private gated entrance, screened-in pool, game room, bar, elevator, and multiple balconies to enjoy the island atmosphere. Located just one block from Siesta Key Village, guests can easily walk to cafes, boutique shops, restaurants, ice cream spots, and live entertainment. brbrWith its luxurious design, private pool, well-appointed kitchen, game room, and prime location near both the beach and Siesta Key Village, The Hideaway by Siesta Key Luxury Rental Properties offers an elevated island retreat perfect for families and groups. brbrBook your stay at The Hideaway today and experience the best of Siesta Key! br br- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property does not allow pets. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Bed

Bath

Sleeps

$837.14

/ Nightly

Private Vacation Home

Location. Four bedroom cottage, one block from beach and Siesta Village

Siesta Key, Florida, United States

Location. Location. Location. Our charming 4 bedroom 3 bath Florida beach cottage, which is over 1800 feet and sleeps 8 with 2 full kitchens and a fully covered porch and large patio in the back unit. Cottage is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7). Enjoy the amazing sunsets each night of your stay without the hassles of traffic, parking and crowds.brbrYou will also be 2 blocks from Siesta Village, with its numerous restaurants, bars and shops. You will feel like a local as you walk or bike and enjoy our special piece of heaven.brbrDowntown Sarasota, which is a brief ride or Uber away, is world renowned and known for its cultural institutions, gourmet restaurants, art galleries, theatre, the John and Mable Ringling Museum of Art, and the Ringlings’ breathtaking home, Ca’d’Zan on Sarasota Bay. Also visit the very entertaining Ringling Circus Museum, brbrAfter a day in the sun, beach combing, boating or shopping enjoy a drink on your private patio after you have taken advantage of the outdoor shower. Your cottage has all the amenities from beach chairs and toys to Wi-Fi and cable and private laundry room.

Bed

Bath

Sleeps

$1697.63

/ Nightly

Private Vacation Home

Sandy Rocks | Ultimate Bundle: 2 Private Pet Friendly Homes, 2 Private Heated Pools, Walk to Beach!

Siesta Key, Florida, United States

Welcome to Sandy Rocks, an exceptional tropical retreat that combines luxury, convenience, and ample space to accommodate your large group or family gathering. This unique property consists of a duplex with 2 units along with a neighboring single family home. The configuration of three units—Crescent Cottage, Sandy Cabana, and Seahorse Cabana—offers a total of 10 bedrooms, 7 full baths, and 2 half baths, ensuring everyone has plenty of room to relax and unwind.brbrCrescent Cottage, the first unit, offers a cozy and inviting atmosphere with its well-appointed bedrooms. With a king bed in the first and second bedrooms, a queen bed in the third bedroom, and two twin beds in the fourth bedroom, along with a sleeper sofa, this cottage comfortably sleeps up to 10 guests. The updated furnishings throughout create a stylish and comfortable space for you to call home during your stay.brbrSandy Cabana, the second unit, offers additional sleeping accommodations and a separate living area. The spacious bedrooms include a king bed in the first bedroom, a queen bed in the second bedroom, and two twin beds in the third bedroom. For added flexibility, there is a queen air bed available, accommodating up to 8 guests.brbrSeahorse Cabana, the third unit, continues the trend of comfort and style. With a king bed in the first bedroom, a queen bed in the second bedroom, and two twin beds in the third bedroom, along with a queen air bed, this cabana accommodates up to 8 guests.brbrInside each unit, you'll find everything you need for a comfortable stay. The three full kitchens are fully equipped with regular and Keurig coffee makers, dishwashers, and all the kitchen essentials you may require. Stay connected with free WiFi and enjoy your favorite shows or movies on the 11 HDTVs throughout the property. Additionally, beach towels, chairs, a cooler, and a caddy are provided for each unit, ensuring you have everything you need for a perfect beach day.brbrExperience the ultimate outdoor living at Sandy Rocks, where you have the luxury of not one, but two private heated pools, ideal for a refreshing swim or sun-soaked relaxation. Indulge in outdoor dining on any of the 3 patios, sharing delectable meals with loved ones amidst the coastal ambiance. Unwind in the poolside hammock, savor a sizzling barbecue from the multiple gas grills, or simply soak up the sun's rays, immersing yourself in the blissful warmth of the Florida sunshine.brbrWhen you're ready to explore the area, you'll find that Sandy Rocks boasts a fantastic location. Just a short drive away, you'll discover the vibrant Siesta Key Village and Siesta Key Beach, offering an array of dining, shopping, and entertainment options. Crescent Beach is only a two-minute walk away, while the South Crescent Village is within a 10-minute stroll, providing you with easy access to the stunning sandy shores and breathtaking sunsets.brbrExclusive Amenities Include:br• 2 Private Heated Poolsbr• Sun Room Facing the Pool Deckbr• Just a Short Drive to Siesta Key Village & Siesta Key Beachbr• A Quick Two Minute Walk to Crescent Beachbr• Duplex home with 2 units, neighboring a single-family homebr• 10 Minute Walk to the South Crescent Villagebr• 10 Bedrooms, 7 Full Baths, 2 Half Bathsbr• 4 King Beds, 3 Queen Beds, 6 twin Bed, 2 Sofa Sleepers, & 1 Queen Air Bed (Sleeps 26) with linens providedbr• Outdoor Dining Spacesbr• 3 Full Kitchensbr• Poolside Hammockbr• Ample Parking Spacesbr• 2 Screened in Porch's With Lounge Areasbr• Free WiFi & 11 HDTV'sbr• 3 Regular & Keurig Coffee Makers, 3 Dishwashers, 3 Washers & Dryers, 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• 3 Gas Grillsbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation Availablebr• Dog-Friendly with a Fee (1 dog up to 25lbs)brbrSandy Rocks can accommodate up to 26 guests with a bedding configuration as follows:brbrCrescent Cottage:br• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: King Bed (1) - Sleeps: 2br• Bedroom # 3: Queen Bed (1) - Sleeps: 2br• Bedroom # 4: Twin Bed (2) - Sleeps: 2br• Extra: Sleeper Sofa (1) - Sleeps: 2brbrSandy Cabana:br● Bedroom # 1: King Bed (1) – Sleeps: 2br● Bedroom # 2: Queen Bed (1) – Sleeps: 2br● Bedroom # 3: Twin Bed (2) – Sleeps: 2br● Extra Bed: Queen Air Bed (1) – Sleeps: 2brbrSeahorse Cabana:br● Bedroom # 1: King Bed (1) – Sleeps: 2br● Bedroom # 2: Queen Bed (1) – Sleeps: 2br● Bedroom # 3: Twin Bed (2) – Sleeps: 2br● Extra Bed: Queen Air Bed (1) – Sleeps: 2brbrWe 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: This pool is heated from November 15th to April 15th. Please contact us if you have any questions regarding the space for this property.

Bed

Bath

Sleeps

$299.43

/ Nightly

Private Vacation Home

Coastal Comfort Steps from Crescent Beach Paradise – Aloha Kai #63 - Roelens

Siesta Key, Florida, United States

Aloha Kai #63 brbrA 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 #63. This charming one-bedroom beach cottage offers the perfect blend of comfort and coastal charm, where the gentle breeze from the Gulf and the lively atmosphere of Crescent Beach set the stage for a truly unforgettable getaway. Thoughtfully designed with a cozy front patio/sunroom that provides a bright, inviting space to unwind after a day in the sun, Aloha Kai #63 invites you to kick off your shoes, sip your morning coffee, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: br1 Bedroom: brMaster Bedroom with King-size bed, Smart TV brAdditional Sleep: Sleeper Sofa in the Living Room brTop 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. 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 Patio/Sunroom: Enjoy your morning coffee or unwind with a good book in the enclosed sunroom, your private nook for peace and relaxation. 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 #63 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 #63 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! br brDISCLAIMERS: br10% deposit is due at time of booking; final payment is due 60 days prior to arrival. Any reservations made within 60 days require full payment. No refunds will be given on deposits. brThis home does not allow pets. brMinimum age requirement of 25 to book. Smoking is not allowed on the property. brEach villa has one designated parking space and parking pass. Additional vehicles and guests must register at the front office for a separate parking pass.

Bed

Bath

Sleeps

$489.93

/ Nightly

Private Vacation Home

Siesta Key FamilyGetaway!!

Siesta Key, Florida, United States

Relax and enjoy, Family get away!brbrBeautiful 4 bedroom house on Siesta Key. Less than a mile away (15 min walk/2 minute drive) from the famous Siesta Key beach and just over a mile to Siesta Key North and South village. Private, resort-style back yard with a saltwater HEATED pool surrounded by a park. Large covered patio with seating and oversized table for family and friends. Gas and Charcoal grill for outdoor cooking. Floor plan perfectly accommodates 1-2 families. Close to all of Siesta Key excitement with enough distance to enjoy a restful Siesta Key vacation.brbrNewly remodeled Kitchen and bathrooms!br

Bed

Bath

Sleeps

$311.71

/ Nightly

Private Vacation Home

Midnight Cove II 524D: 3-Bedroom Townhouse Steps from the Pool in Siesta Key

Siesta Key, Florida, United States

Welcome to Midnight Cove II 524D! This beautifully refreshed 3-bedroom, 2.5-bathroom townhouse is perfect for families or groups of up to six people seeking a relaxing retreat in Siesta Key. Ideally located directly in front of the stunning pool area and just a short stroll to the beach, this unit offers easy access to everything our vibrant community has to offer, including shopping, dining, and local art and culture.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Siesta Key Beach and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, you’ll find a spacious living area featuring a large TV that opens to a screened-in lanai with a dining table, perfect for enjoying meals outdoors. The gorgeous kitchen boasts stainless steel appliances, a stylish kitchen island, and a modern dining table, making meal prep a delight. brbrUpstairs, the primary bedroom features a luxurious king bed, a private balcony, and an ensuite bathroom with a walk-in shower. The second bedroom includes a comfortable queen bed, while the whimsical third bedroom is perfect for kids, furnished with two twin beds. These rooms share a convenient hall bath with a shower-tub combo. brbrBook your stay at Midnight Cove II 524D today and enjoy the best of Siesta Key living! Unwind in this stylish townhouse and make lasting memories by the beach!

Bed

Bath

Sleeps

$638.45

/ Nightly

Private Vacation Home

4 Bedroom Pool Home Siesta Key

Siesta Key, Florida, United States

Our 3 story home creates privacy for multiple families to enjoy. Located 1 mile from the public beach. The village for shopping & dining is a few mins shuttle ride. Inside you will find smart TV's in each bedroom, fully stocked granite kitchen, full laundry room & plenty of beach chairs. Two of the bedrooms have their own private bathroom. Private pool with fully covered outdoor dining area, amongst the salty air & gorgeous palm trees.

Bed

Bath

Sleeps

$485.27

/ Nightly

Private Vacation Home

Siesta Zen – 2BR Steps to Siesta Key Beach & Village!

Siesta Key, Florida, United States

Siesta ZenbrTropical island cottage, remodeled in 2025 with private patio! 1-min walk to best beach in the country. 4-min walk to world-famous Siesta Village. Spend days on white quartz-sand beaches with calm water and nights enjoying the Village's live music drinks and fresh seafood. For totally effortless moments, dine drink or relax on your own tropical patio. Book your Siesta Zen escape now. - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Beaches – 2-min walk to award-winning beachesbr∙ The Village – 4-min walk to world famous Siesta Villagebr∙ Relaxing - private garden patio with grill and alfresco dining br∙ Sunsets –2-min walk to best sunsets in America br∙ 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 - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ Island Trolleys - you're already where you want to be, but they're fun:)br∙ The Memories - one of a kind Siesta Key experience, favorite of initiated visitorsbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is 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. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrThe HomebrThe right vacation unit makes all the difference. This cottage is quiet, was fully remodeled in 2025, and it's close to everything. Your patio is 100% private fenced in and surrounded by tropical plants with gas grill and dining table. It's perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal. It's a 4-minute walk off the patio to the Siesta Key Village and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island. It's just a 2-minute walk to the sand path for the best beach on the island. brbrBedroom DetailsbrThis 2BR house is ground floor with just a few steps at the entrance. Bedrooms include a sunny queen master BR, second bedroom containing 2 full beds, and a sofa in the living room. Need more space We can get you a tempur-pedic rollaway bed 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. brbrbrTermsbrPayments 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.

Bed

Bath

Sleeps

$976.65

/ Nightly

Private Vacation Home

5-Bedroom house on Siesta Key - walk to beach or village

Siesta Key, Florida, United States

Your Siesta Key adventure begins at this fabulous 5-bedroom house. The house is complete with a pool & hot tub with views down the canal that is great for fishing off the dock. With 3 king beds, 3 queen beds, and 1 twin bed, this delightful property offers a welcoming atmosphere for guests. Two family rooms makes it great for multigenerational families to be together but have plenty of space to spread out. This home ensures a comfortable stay. The home is 150 yards from the main beach entrance and a block from the free trolley pickup that can take you to the village. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.

5

Bed

4

Bath

13

Sleeps

$687.33

/ Nightly

Private Vacation Home

Waterfront Home with Pool & Dock

Siesta Key, Florida, United States

Summary:brbrEscape to your peaceful waterfront home near Siesta Key, where comfort, space, and outdoor living come together for a true Florida retreat. This spacious 4Bedroom, 2.5Bathroom home is ideal for families, couples, or groups, offering bright open interiors and private resort-style outdoor amenities designed for relaxation.brbrbrbrThe Space:brbrStep inside to an inviting living space with comfortable sofas, a cozy fireplace, and large French doors that open to the patio, creating a seamless indoor-outdoor flow. The fully equipped kitchen, complete with a modern island and bar seating, makes gathering for meals effortless, while stylish bedrooms and modern bathrooms with walk-in showers offer comfort after a day in the sun.brbrbrbrWhat makes this stay special is the way the home blends indoor comfort with outdoor living. Spend your days lounging by the private swimming pool, grilling at the outdoor bar & BBQ area, or unwinding in the covered patio lounge overlooking the canal. The private dock offers direct waterfront access for fishing, launching a kayak, or simply enjoying peaceful water views.brbrbrbrOutdoor Amenitiesbrbr• Private swimming poolbrbr• Covered patio with lounge seatingbrbr• Outdoor bar and grillbrbr• Private dock on the canalbrbr• Waterfront seating area for sunset viewsbrbrbrbrGuest Access:brbrGuests have exclusive private access to the entire home, including all indoor spaces, the private pool, covered patio, outdoor entertaining areas, and private dock.brbrbrbrThe Neighborhood:brbrNear to Siesta Key Beach, you’ll be close to world-famous white sand beaches, Siesta Village restaurants and shops, and nearby attractions such as Turtle Beach, waterfront dining, and local parks. The location offers the perfect balance of peaceful waterfront living and easy access to everything the area has to offer.brbrbrbrOther Things to Note:brbrThe home is located directly on a canal. Guests, especially those with children, should be mindful around the private dock. Life jackets are not provided, so please bring your own if you plan to use kayaks or other watercraft.brbrbrbrInteraction with Guests:brbrEnjoy a seamless self-check-in experience and complete privacy during your stay. While we won’t be on-site, we are always available through the messaging app or by phone if you need assistance.

Bed

Bath

Sleeps

$313.93

/ Nightly

Private Vacation Home

Our House at the Beach C-118 Coastal Haven Retreat

Siesta Key, Florida, United States

First floor townhouse, few steps inside and outside, no elevator. brbrThis luxurious Lake House townhome directly adjacent to America's famed #1 beach - Siesta Beach, offers a spacious bi-level layout that includes separate dining and living rooms with Brazilian cherry hardwood floors. The eat-in kitchen is fully stocked with pots, pans, dishes and flatware and a suite of stainless steel appliances including a dishwasher, refrigerator, glass top range and built-in microwave. The laundry includes a full size washer and dryer for your convenience. The large living room features theater-style leather seating, a queen size murphy bed and a balcony overlooking the lake. The master bedroom suite also opens onto the balcony and has an en-suite bathroom with walk-in shower and rain shower feature, closet and dressing area. The second bedroom has an adjacent full second bathroom. The unit offers central A/C, flat screen HD TV in each bedroom and a large flat screen HD TV with Direct TV and streaming access, Blu-ray disc player with theater sound speakers in the living room. Private garage parking for one car is included. Special amenities in this unit include soundproof bedroom windows, free wireless internet, free calls to the USA, Canada and Puerto Rico and road bikes. The development includes a private pool, covered pavilion area with gas BBQ, a picnic area and tennis courts.

Bed

Bath

Sleeps

$294.73

/ Nightly

Private Vacation Home

Our House at the Beach C-215 A Wave From It All

Siesta Key, Florida, United States

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

2

Bed

2

Bath

6

Sleeps

$311.71

/ Nightly

Private Vacation Home

Midnight Cove II 221D - Serene Bayfront Vacation Rental!

Siesta Key, Florida, United States

Experience the perfect getaway at Midnight Cove II 221 D with this charming 3-bedroom, 2.5-bath townhouse. This stunning bayside condominium complex features private beach access to Siesta Key Beach, known for its world-renowned pure white sands and breathtaking sunsets. Ideal for families or groups, this retreat is just minutes away from the heated pool and beach, combining comfort and convenience for an unforgettable stay.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Siesta Key Beach and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, the recently renovated townhouse boasts a cozy living room equipped with a flat-screen TV, perfect for relaxing after a day in the sun. The fully equipped kitchen features modern appliances and ample counter space for meal preparation, with an inviting dining area for family gatherings. The primary bedroom offers a queen bed and a sunny open balcony, while the additional bedrooms include another queen bed and a twin bed, providing ample comfort for your group. A convenient Jack and Jill bathroom ensures easy access for all guests.brbrReady to experience the beauty of Siesta Key Book your stay at Midnight Cove IITtoday and enjoy all the luxury and amenities this spectacular property has to offer!

3

Bed

1

Bath

6

Sleeps

Vacation Home Rentals By Owner In Siesta Key, FL

$473.96

$367.14

$1460.6

$366.71

$1428.65

$382.11

$618.34

$832.74

$837.14

$1697.63

$299.43

$489.93

$311.71

$638.45

$485.27

$976.65

$687.33

$313.93

$294.73

$311.71

Rent a place that suits your needs

Most popular vacation rentals in Siesta Key

$2522.03

$2135.02

$2157.13

$2193.20

$2342.88

$2445.50

$2479.18

$3229.57

$3133.33

$3110.58

Most Popular Cities in Florida