Vacation Rentals By Owner In Siesta Key, FL

Welcome to Just Beachy, a beautifully updated beachfront condo offering the perfect blend of modern comfort and laid-back charm. With partial views of the Gulf and direct access to Siesta Key’s world-famous white sand and crystal-clear waters, this 3-bedroom, 2.5-bathroom retreat is designed for unforgettable getaways. Whether you're heading out for a beach day or strolling into Siesta Key Village for dining and nightlife, Just Beachy puts you in the heart of it all. With its unbeatable location and relaxing atmosphere, this coastal haven is sure to become your go-to vacation spot year after year.br*This property is stairs only; all guest must have the ability to climb stairs.brbrBedding and Television:brMaster Bedroom - queen, TVbrBedroom 2 - 2 twins, TVbrBedroom 3 - sleeper sofa / office space, TVbrLiving Room - TVbrbrAdded 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: 27br*Security Authorization Hold taken upon check-in. Amount: $1,000

Private Condo W/ Direct Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$407.6

Enjoy this beautiful two bedroom, two bath villa, featuring a view of the intercoastal and neighboring yacht club Marina.brbrGuests have deeded access to the private beach at Gulf and Bay Club, making one of the world’s most famous beach destinations an easy walk away.brbrThis ground floor property is just steps to the one of two large community pools, as well as the fishing pier, exercise room, sauna and grills in this gated resort community. Enjoy the lighted tennis courts, ponds stocked with fish, and walking paths.brBoth bedrooms have a TV and plenty of closet space. The plantation shutters allow you to let the sunshine in or darken the room for a great night’s sleep. There won't be much you need to bring with our fully equipped kitchen, linens, beach towels, full-size washer and dryer & high speed internet.brGuest reservations also include use of the beach cart, chairs, pool and beach toys, bikes and fishing gear stored in the garage.brWalk to the Village for great food, shopping, entertainment or ice cream, or walk 1 1/2 miles on the beach to the Point of Rocks. There is something for everyone!

Villa

Stay In Our Ground Floor Villa, Perfectly Located Between The Pool And The Bay.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$218.75

Step out the back door of your ground floor apartment and in seconds you're standing on a boating and fishing dock, surrounded by lush tropical foliage. This breathtakingly Beautiful two bedroom, 2 bath unit, recently remodeled, is located in Midnight Cove, one of the best complexes on Siesta Key. Since Midnight Cove has buildings on the Gulf as well as Bay side of Midnight Pass Road, you have a private beach access and access to all the amenities on both sides of the island, which include a marina, two tennis courts, two heated pools, beach chairs, lounges, and umbrellas. The condominium is located on Bay side of the island, just across the street from the world-famous Siesta Beach, which has powdery white quartz sand (it doesn't get hot on your feet). Siesta Key Beach was declared the 'best beach in the USA' by Dr. Beach in 2011. Your bayside apartment has a view of the canal and boat dock which is bordered by lush mangroves. It's a tropical ambiance unmatched by any other condominium!brbrThe highlight of this luxurious and spacious apartment is its immense screened lanai off the living room with a view of the bay and tropical mangroves. The living room, furnished in Florida style, has a pull-out sofa, cable TV, DVD, VCR. The master has a king size bed and TV, and the master bath has a tub-shower combo. The second bedroom has two twin size beds and TV with a half bath right off the bedroom. The kitchen is totally equipped, including frig with icemaker, dishwater, and microwave. A washer-dryer combo (two large washers and dryers) has just been installed in the apartment. The Siesta Cove complex stretches over 11 acres of lush tropical greenery to the serene waters of the Intercoastal Waterway.brbrThe complex has two heated pools, two combined tennis/pickle ball courts, marina and boat dock, basketball hoop, and, most importantly, your own private beach access on a private beach. No need to get in your car, as two blocks away there is a convenience grocery store, drug store, post office, liquor store, marina, and an assortment of shops and restaurants. Siesta Key Village is a mile down on the north end of the island and offers many quaint shops, restaurants and nightly entertainment. It's a 'must' to explore the art and culture of downtown Sarasota: The historical grounds of the Ringling Museum on Sarasota Bay, the posh shops of St. Armands Circle, the historical Asolo Theater, and the world- renowned Van Wezel Concert Hall featuring the Florida West Coast Symphony. You are 25 minutes away from Sarasota-Bradenton International Airport, featuring direct flights from New York and other major cities, and 60 miles from Tampa International Airport. Free high-speed internet and wi-fi.brPlease, no dogs or cats.

Midnight Cove Bayside

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$392.69

Enjoy your beach side vacation condo here in Siesta Key, with perfect sandy beaches just a short walk from your door. Siesta Key is a barrier island along the southwestern coast of Florida and is considered by beach experts to be one of the most beautiful beaches in Florida. When you stay with us at Siesta Dunes Condominiums, you stay in style and comfort, just a short walk from the lovely beach.brbrLet’s face reality. If you’re coming to Siesta Key, you want to be on the beach. You'll appreciate the privacy and value when you skip the crowded hotels, and stay in a vacation condo. And if you enjoy playing with other people while on vacation, look forward to our saltwater pool, hot tub, beach side grill, beach deck and more.brbrThe sun-washed colors of Siesta Key are the inspiration for this relaxed 1st floor garden unit. The glassed in lanai provides direct access to the garden and outdoor patio. The unit has a clean, updated feel. The master bedroom has 2 queen beds and the guest bedroom has 2 twins. Amenities include 3 Flat Screen TV s (New 58 Inch Tv in Living Area), DVD Player, Stereo Available, Carpet and Tile Flooring, Wireless Internet Access and Washer and Dryer

Beach Inspired, Eclectic Garden View

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$333.48

GEM at Barefoot BungalowsbrbrWelcome to “GEM” at Barefoot Bungalows, located in the heart of Siesta Key. What truly sets this property apart is the location — you’re just steps from Beach Access #2 and #3 and only two blocks from Siesta Key Village. Guests can walk everywhere — beach, dining, nightlife — *no car needed*brbrThis is a second-floor, 2-bedroom, 1-bath villa occupying the entire upper level of this classic 1945 triplex. It offers that “Old Florida” beach cottage charm that’s increasingly rare on the island, especially at this price point. Stairs less to 2. nd floor brbrInside the UnitbrbrThe layout is efficient and comfortable:brbrKing bed in the primary bedroom private balconybrbrQueen bed in the second bedroombrbrFull bathroom with shower/tub combinationbrbrOpen living area with TV and WiFibrbrFully stocked kitchen with full-size refrigerator, stove/oven, microwave, and KeurigbrbrThe private balcony is a standout feature. It gives guests true outdoor space — ideal for morning coffee before walking the beach.brbrWhether you're here for a relaxing beach escape, a romantic getaway, or an extended winter stay, Siesta Key offers the perfect blend of laid-back island charm and vibrant coastal energy.

A GEM on Siesta Key close to Village - 2BR w Balcony, 1945 Triplex 2nd Floor

Siesta Key, Florida, United States

Bed

1

Bath

Sleeps

$733.17

Gertrude's Village HousebrTop location on the island with 3 patios and private gate into world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Enjoy private patios off the bedrooms and living area. Gertrude's is sure to provide a combination of fun ease and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Beaches – 1-min walk to award-winning beachesbr∙ The Village – 10 steps to private gate into world famous Siesta Villagebr∙ Relaxing – three private patios off bedrooms and living areabr∙ Sunsets – 1-min walk to best sunsets in America & 300-degree Gulf 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 - 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 HomebrYou work hard, you deserve this. Three patios are 100% private and surrounded by tropical plants with shade umbrellas, chaise loungers and dining tables. Perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal. It's a few a steps off the patio to a private gate into the heart of the Village and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom DetailsbrThis 3BR house is ground floor. Bedrooms include a king BR with French doors to a private patio, a queen suite with door to a private patio and bath, one bunk bed BR containing 2 twin over 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.brbrbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. 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. brbrHistorybr“Life is a string of pearls where you never know how many you have left.” - GVLJ. Gertrude Rentals was named for my grandmother “Gertrude” who traveled the world until age 91 but always insisted Siesta Key was the place she loved best. When I was young, she would take me to the beach and swim out so far, I couldn't see her yellow flowered bathing cap even while standing on a chair! Today, you can laze float and wade in the same white quartz sand and calm crystal-clear gulf water she once did. 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's Siesta | Top Location! 1-min to Best Beaches, Private Patios, Gate to Village!

Siesta Key, Florida, United States

3

Bed

Bath

10

Sleeps

$364.95

The Village StudiobrTop location on the island! Apartment with full kitchen, private patio, quiet gated courtyard, in world famous Siesta Key Village! Leave the car behind and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach with calm water, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. This studio apartment delivers a combination of fun ease and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabr brbrWhat Guests Lovebr∙ Beaches – 2-min walk on quiet street to award-winning beachesbr∙ The Village – 100 steps to world famous Siesta Villagebr∙ Relaxing – private patio in peaceful gated courtyardbr∙ Sunsets – 2-min walk to best sunsets in America & 300-degree Gulf 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∙ The Essentials – full kitchen, patio, grill, queen bed, cable, Wi-Fi, onsite laundry br∙ The Memories - one of a kind Siesta Key experience, favorite of initiated visitors br∙ Island Trolleys - you're already where you want to be, but they're fun:)brbrbrThe 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 HomebrYou work hard and deserve a getaway. This apartment is ground floor with a queen bed, full kitchen with fold-down table for two, and bathroom with step-in shower. Your patio is private and has chaise loungers, bistro dining table, propane grill, and is on a quiet gated courtyard. Perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal. It's a few a steps off the patio into the heart of the Village and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, 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. brbrHistorybr“Life is a string of pearls where you never know how many you have left.” - GVLJ. Gertrude Rentals was named for my grandmother “Gertrude” who traveled the world until age 91 but always insisted Siesta Key was the place she loved best. When I was young, she would take me to the beach and swim out so far, I couldn't see her yellow flowered bathing cap even while standing on a chair! Today, you can laze float and wade in the same white quartz sand and calm crystal-clear gulf water she once did. 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.

Apartment

Walk to Siesta Key Beach & Village | Private Patio | Prime Location!

Siesta Key, Florida, United States

1

Bed

1

Bath

Sleeps

$277.85

Jamaica Royale Unit 055 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 055, a beautifully decorated one bedroom, one bathroom end unit with a queen sleeper sofa and peaceful garden and pool views. Located in the highly sought after Jamaica Royale community on Siesta Key, this light filled retreat is just a short walk from private beach access to the world-famous Siesta Beach. With renovated interiors as of June 2025, this condo is ideal for couples or small families seeking comfort, convenience, and the best of coastal living.brbrHighlightsbr• 5-minute walk to Siesta Beach via private beach accessbr• 1 bedroom, 1 bathroombr• 1 king bed, 1 queen sleeper sofabr• End unit with garden and pool viewsbr• 3 heated community poolsbr• Private patiobr• Shared BBQ and picnic areabr• Washer and dryerbr• Assigned covered parkingbrbrStep outside your patio door and enjoy easy access to the beautifully landscaped garden area and one of three heated pools within the community. Spend your days lounging by the water, strolling to the private beach access on Siesta Beach, or grilling at the shared picnic area. From tropical landscaping to convenient on-site amenities, Jamaica Royale offers a relaxing, resort style environment perfect for unwinding.brbrInside, this condo features a bright and inviting living area with comfortable seating, a flat screen TV, and a queen sleeper sofa for additional guests. The kitchen is well equipped with cookware, utensils, and appliances, making it easy to prepare meals at home. A dining table for four provides a cheerful space for breakfast or casual dinners before heading out to explore Siesta Key.brbrThe primary bedroom showcases elegant furnishings, a king bed, and plenty of storage space. The shared hallway bathroom includes a walk-in shower and a single vanity. This layout is designed to offer comfort and simplicity after sunny beach filled days.brbrRoom Detailsbr- Primary Bedroom: King bedbr- Living Room: Queen sleeper sofabr- Bathroom: Shared hallway bath, walk in shower, single vanitybrbrGuests will enjoy in unit washer and dryer, Wi-Fi, community shuffleboard courts, outdoor showers, shared grills, and easy access to Siesta Key’s restaurants, shops, and island trolley. Covered parking is provided for added convenience.brbrFrom relaxing poolside to enjoying sunset walks along Siesta Beach, Jamaica Royale Unit 055 offers the perfect setting for your next island escape. Book your stay with Tropical Sands Accommodations and experience the comfort, location, and coastal charm of Siesta Key.

Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 055

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$425.68

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Crystal Sands Villa! brbr brbrExperience the ultimate Siesta Key lifestyle in this stunning, freshly renovated free-standing villa. Located in the highly sought-after Crystal Sands complex, this rare detached home offers the perfect blend of luxury, privacy, and resort-style amenities. Whether you’re lounging by the Gulf-front pool or walking the lighted path to your private stretch of Crescent Beach, this is the coastal retreat you’ve been looking for. brbr brbrLOCATION HIGHLIGHTS: brbr- Exclusive Beach Access: Steps from a private, gated beach with a beautiful lighted evening walkway. brbr- Resort Amenities: Access to two heated pools—one of which directly overlooks the turquoise waters of the Gulf. brbr- Island Exploring: Located on the Free Siesta Key Trolley route for easy trips to the Village. brbr- Adventure Awaits: Walking distance to boat, jet ski, and parasailing rentals. brbr- Walkable Dining: Stroll to local favorites like Clayton’s Grill, Miguel’s, and the Orange Octopus for gelato. brbr brbrPROPERTY FEATURES: brbr- Private & Spacious: Rare ground-floor, free-standing villa (no neighbors above or below). brbr- Modern Renovations: Sleek quartz countertops, new GE appliances, and high-end finishes throughout. brbr- Attached Garage: Convenience and extra storage for your beach gear. brbr- Tech-Ready: Dedicated high-speed WiFi and Smart TVs in the living room and master suite. brbr- Laundry: Brand new, full-size LG washer and dryer in-unit. brbr brbrLIVING ROOM: brbr- Open Concept: A bright, airy layout featuring floor-to-ceiling sliders that flood the home with natural light. brbr- Climate-Controlled Sunroom: Enjoy the additional living area with a dedicated AC unit—perfect as a reading nook or extra sleeping space with the convertible sleeper. brbr- Dining: Fully stocked with cookware, dishes, and essentials and a modern dining table with seating for 6. brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Suite: King-size bed, his-and-hers closets, and a renovated ensuite bathroom featuring a custom walk-in tiled shower and quartz vanity. brbr- Guest Bedroom: Two comfortable twin beds with plenty of storage and a dedicated cable TV. brbr- Guest Bathroom: Features a tub/shower combination with updated quartz finishes. brbr brbrEXTRA PERKS: brbr- Beach Ready: We provide beach chairs, an umbrella, and fresh beach towels for your convenience. brbr- Concierge Touch: Professionally cleaned and fully stocked with essentials to start your vacation. brbr brbrLOCAL FAVORITES: brbr- Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery, and more within walking distance brbr- Boat & water sport rentals nearby brbr brbrIMPORTANT INFO: brbr- No pets brbr- No smoking or vaping indoors (outdoors only, away from windows/doors) brbr- Rental registration required brbr brbrDON'T JUST VISIT THE BEACH - LIVE THE SIESTA KEY LIFESTYLE. BOOK YOUR STAY NOW!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Private Beach & Gulf-Front Pool Modern Free-Standing Villa at Crystal Sands

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$342.51

Welcome to Casa Covella, a private villa in the Polynesian Garden community located in beautiful Siesta Key, Florida.brbrBe sure to have your breath taken away when you enter this 1900 square foot Siesta Key Villa, equipped with absolutely everything you would need to have the best vacation possible. As you enter the unit, you are surrounded with modern beach decor, spacious kitchen, dining room table, and additional bar style seating. The home has a beautiful lanai attached to the main living area to relax in beautiful outdoor Florida weather. This property is made with the renter in mind, as it provides every additional detail, including kitchen essentials for those dinners indoors, an Xbox 360 on the lanai for some video games, a pool table in the garage, as well as complimentary beach gear along with beach cruiser bikes for your use....all included!! No need to spend additional money on renting items when you rent this property...as it has everything setup for you.brbrThe home sleeps 6 people comfortably, with a King sized bed in the Master Suite featuring its own private bathroom with a walk in shower. The Guest Bedrooms feature both a Queen sized mattress in one room and Two Twin Singles in the second room, giving you options for both adults and children! There is a very spacious guest bathroom for all to utilize, including extra linens, a his/her sink, and a walk in shower....giving plenty of space to everyone. There is also an office space in the property with a really comfortable day bed!brbrWe know you aren't visiting Florida for just the home....you want to spend time outdoors!! No better place to do so then right at Casa Covella. There is more than enough private outdoor seating that surrounds the property for you and your guests to use! The beautiful community at Polynesian Gardens also provides its own amenities that make Casa Covella even more of a highlight destination, including a community Heated Pool, and inter-coastal seating to view the canal! We cant wait to host you in Siesta Key! brbrThis property does not allow pets, service animals included. For more photos and reviews, visit www.CasaCovella.com

Villa

Welcome to Casa Covella in Polynesian Gardens

Siesta Key, Florida, United States

3

Bed

Bath

6

Sleeps

$22628.25

Modern Wellness Sanctuary at Siesta Key: 512 Treasure Boat WaybrbrExperience the pinnacle of serene living in our chic, minimalist-designed home on Siesta Key. This modern wellness sanctuary, nestled at 512 Treasure Boat Way, is a haven of tranquility with calming tones, sophisticated lighting, and an expansive, open floor plan.brbrKey Features:brbr • Chef’s Kitchen: Perfect for culinary adventures.br • Prime Location: Walking distance to Siesta Key villages, gourmet dining, and picturesque beaches.br • Nautical Access: Situated on a canal for direct sea access.br • Wellness-Focused Amenities: Comprehensive in-home gym, outdoor yoga/meditation space, saltwater heated pool with full-house water filtration, and spa-like bathrooms with pebble finishes.br • Eco-Conscious Living: Premium air quality units, HEPA-filtered ACs, low VOC paints, and a fully recycled air system. Regularly sanitized air ducts for optimal indoor air quality.br • Family-Friendly: Close to prestigious Out-of-Door Academy and top public schools.br • Safety First: Hurricane-impact resistant windows with low heat index and UV protection.br • Outdoor Bliss: Fire pit and seating area on the lanai, mature landscaping, and fresh mangoes from the backyard.br • Green Living: Complimentary green cleaning crew for a toxin-free environment.br • Furnishing: Tastefully done in neutral, calming tones.brbrIdeal for garden enthusiasts, the side patio offers space for gardening and bistro dining. Enjoy the beautiful fire pit and seating area for entertaining guests. Revel in the lush surroundings and indulge in wellness with the property’s comprehensive features.brbrLocation Perks:brbr • Explore the natural beauty and local attractions of Siesta Key.br • Enjoy the convenience of nearby shopping and entertainment options.brbrDetails:brbr • Bedrooms & Bathrooms: [Insert number of bedrooms and bathrooms here]br • Available for $20,000/monthbrbrThis property is not just a home, but a lifestyle choice for those who value tranquility, wellness, and a connection with nature. Book your stay at this serene Siesta Key sanctuary and embrace a life of modern luxury and wellness.

Luxury Siesta Key Wellness Retreat. 5-10 min walk to Siesta Beach and Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.3

Condo underwent complete rehab in 2025. Everything brand new including all furniture, appliances, floors, baths, and mattresses.brbrExperience spectacular intracoastal bay views in this FULL BAYFRONT condo. Relax while watching the parade of boats in the bay through the custom trifold sliding doors on the lanai or walk outside to the private patio equipped with outdoor chairs. This unit is directly on the path to the new private fishing pier.brbrFirst floor means there are no steps to climb. Condo has been professionally remodeled and impeccably maintained. This unit features 2 bedrooms/2 full bathrooms with quartz counter tops, custom quality cabinetry, and stainless steel kitchen appliances. Brand new in unit washer and dryer. Plenty of storage available in a large custom walk in closet. Designated parking spot right in front of condo. brbrPeppertree Bay is a Bay to Beach association with private beach access. Guests can enjoy a day in the powdered sugar sands of Siesta Key beach in private lounge chairs or cabanas right on the beach. Property has two pools nestled in a paradise setting - one pool on bay side and one beach front. brbrCondo has a stop right in front of building on the FREE Trolley line that will take you north to Siesta Key Village or south to Turtle Beach. brbrPeppertree Bay requires renters to submit an application with $100 fee. brbr***Monthly rentals only, no exceptions*** brNo pets allowed by HOAbrbrBedrooms:brMaster has king sized bed with new mattress brGuest room has two twin beds with new mattressesbrbrBaths:brBoth baths have walk in showers / no bathtubsbrbrElectronics:brLiving room has brand new 4K UHD 55” flat screen Smart tv with DVR brMaster Bedroom - 43” flat screen Smart tvbrGuest bedroom – 32” flat panelbrFree high speed WiFi / Internet

First floor Stunning Siesta Key-2B/2B Bayfront. Completely renovated in 2025.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$220.19

Recently renovated two bedroom, two bath condo with a view of the inter coastal water ways of Sarasota and Siesta Key. Harbor Towers Yacht and Racquet has all you need for a perfect vacation including a heated pool, tennis courts, exercise room, grilling patio, marina and is within a half mile of Siesta Key Beach. Siesta Key Village is two miles away and has many restaurants and shops. There are bike, kayak and boat rental facilities within 2 miles. Our unit has newly updated kitchen and bathrooms and has it's own washer and dryer in the unit. We have free wifi in the unit and cable on all three televisions. The living room has a sofa sleeper and each bedroom has a king bed. Siesta Key beach is a quarter mile away and the island has a free trolley service amongst other free ride services. The kitchen is well equipped and there are beach chairs, coolers towels and a beach cart for you to enjoy a day at the beach. Tennis racquets are also available for the tennis players.

Within walking distance of Siesta Key Beach!! Beautiful view of bay!!

Siesta Key, Florida, United States

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Sleeps

$434.13

Beautiful, remodeled and professionally decorated 3rd floor garden view condo. Tile floors throughout, granite counter tops and maple cabinets. French doors lead to the glassed door lanai with partial gulf views. The unique second bedroom and bath can be closed off to make them another private suite.brbrAmenities Include:brbrGarden ViewbrbrKing Bed in the Master BedroombrbrShower in Master BathroombrbrTwo Twin Beds in the Guest BedroombrbrBathtub/shower in Guest BathroombrbrSleeper Sofa in Living AreabrbrAll Granite CountertopsbrbrTravertine Floors Throughout Unitbrbr3 Flat Screen TV'sbrbr2 DVD playerbrbrWireless Internet AccessbrbrWasher/Dryer in Guest Closet

Beautifully Updated & Decorated Gulf Side Garden View Condo

Siesta Key, Florida, United States

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Bath

Sleeps

$403.66

Unit 1-306 is meticulously equipped, maintained & furnished with a bright open concept. The unit is updated to provide all the comforts of home. Unit 1-306 has a screened lanai offering views of the Gulf with seating for 4 – perfect for enjoying your morning coffee, cocktail hour & meals. Sleeping accommodations feature a king-size bed in the primary bedroom & ensuite bathroom; the second bedroom is cozy with 2 twin beds. Both bedrooms have beds with quality mattresses and bedding, excellent lighting, walk-in closets, dressers, nightstands & smart tvs. The bathrooms are modern & have ample counter space & excellent lighting. The kitchen has stainless steel appliances, ample cookware & dishes and is clean & fully equipped; the adjacent dining room accommodates 6 people & has additional bar seating for 3. The living room is spacious & has a 50” flat screen smart tv. Sleek tile floors & newer laminate flooring throughout the unit.

Tastefully Furnished, Fully Equipped Condo at Siesta Dunes, 1-306

Siesta Key, Florida, United States

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Sleeps

$317.89

Escape to the tranquil beauty of Siesta Key in this inviting 2-bedroom, 2-bath condo located in the picturesque Bay Oaks community. Surrounded by mature live oak trees, lush landscaping, and access to peaceful bayfront views, this charming 4th-floor retreat offers comfort, convenience, and the perfect beach getaway.brbrProperty Highlights:br•Located in the scenic Bay Oaks complex on Siesta Key's baysidebr•Lined with beautiful live oak trees and manicured tropical landscapingbr•Short drive to world-famous Siesta Key Beach for sun, sand, and sunsetsbr•Access to heated swimming pool, tennis court, and private bayside dock—great for fishing or watching boats glide bybr•Includes plenty of beach essentials: chairs, umbrella, and morebrbrCondo Features:br•Situated on the 4th floor with elevator accessbr•Cozy, open living space with coastal-inspired decor and plenty of natural lightbr•Closed-in porch with large sliders—open for fresh Gulf breezes or enjoy views of the garden and a peek of the Gulf in the distancebrbrBedrooms and Bathrooms:br•Primary bedroom includes a king-size bed, plush linens, a SMART TV, walk-in closet, and ensuite bathroom. Ensuite features a separate vanity area and a pocket door leading to a walk-in showerbr•Guest bedroom has two twin beds, a SMART TV, walk-in closet, and ensuite access to a full bathroom. Guest bathroom offers dual entry from the hallway and guest room, with a shower/tub combo, plush towels, and a vanitybrbrKitchen and Amenities:br•Fully equipped kitchen with all white appliances and everything needed for cooking and dining inbr•Private in-unit washer and dryer for added conveniencebr•Dining table and comfortable seating for relaxing evenings at homebrbrWhether you're lounging by the pool, taking a stroll to the beach, or relaxing in the comfort of your breezy porch, this Bay Oaks condo offers the perfect blend of coastal charm, privacy, and resort-style amenities. Ideal for couples, families, or snowbirds looking to enjoy the Siesta Key lifestyle in a serene, well-kept community.brbrThe Beauty of Siesta KeybrSiesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. brbrThe Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate.

Mins to Beach, Tennis, Heated Pool, Bayside Private Dock

Siesta Key, Florida, United States

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Sleeps

$894

Aylee`s tropical 4 bedroom, 3 bathroom, saltwater pool, gourmet double kitchen home oasis… is the perfect destination for those seeking relaxation, adventure, and everything in between. Located on one of Sarasota’s charming barrier Islands, Siesta Key Island. Aylee`s Beach House offers comfort and luxurious accommodations just 360 feet from the crystal-clear waters of the Gulf of America. Take a leisurely stroll along the soft white sands of Siesta Beach, the #1 ranked beach in America known for its stunning beauty, cool to the feet crystal white sand & gorgeous emerald water. Indulge in delicious seafood in the village or browse through the quaint shops. Book your stay today and escape to a little piece of paradise.brNo Smoking or Vaping inside the home on Property. Smoking and Vaping OUTSIDE ONLY with doors to home closed. Do not dispose of cigarette buds on the ground.

Aylee`s Beach House| 360 steps from Siesta Key Beach|4 BR 3 BA |Saltwater Pool

Siesta Key, Florida, United States

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3

Bath

12

Sleeps

$307.42

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a heated pool, tennis courts and a covered pavilion with grilling area.

Our House at the Beach E-102 Modern, light-filled, spacious

Siesta Key, Florida, United States

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Bath

Sleeps

$562.25

Oceanfront on BEACH! Imagine waking up to jaw dropping views of the beach and ocean with the sound of gental waves. Total remodel. freshly painted, custom showers, rain shower head, body jets and wand.brbrKitchen: pull-out faucet, mosaic tile backsplash, quartz tops,under cabinet task lighting, stainless appliances w ice maker. leather swivel, rocker, recliner. 3 flat screen Tv’s. brSuper-Fast internet: New modem & Router 383 mbps upload 74.6 download brBuilt-in rapid charge 40 watt type C & A USB ports in every room. br . King size mattress same one the Property Brothers use on TV shows. HUGE Walk-in closet. Lanai: stunning front corner condo with ocean & beach views!! wrap around lanai with rockering chairs and 3 piece dinette set. Special features: * Anti fog, lighted 48” vanity mirror. *Pocket Sliding glass doors for better ocean views. *Extra small refrigerator br *****Two BBQ gas grillsbrbr***Gated community- Keyless entry to gate, pool, building, and condo. br***Carport included br***Luggage and grocery carts are available at the entrance. brPerfect locationbr steps to Crescent grocery, restaurants, boating, wave runners, bikes, paddle boards, shopping, 7-11, hair salon, three ice cream shops. Bags of ice available on-site in clubhouse. brbr*** Note: Property is keyless. Codes, Badges and keyfobs are provided. Beach lounge chairs and chairs provided. Beach attendant installs beach umbrellas or cabanas for an additional charge.

It's about location! Beachfront, Oceanfront, bright & airy

Siesta Key, Florida, United States

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