Vacation Rentals By Owner In Siesta Key, FL

Enjoy this darling 1-Bed, 1-Bath condo, located just half a block from the powdery white sand of the world-famous Siesta Key Beach! With a lovely open floor plan, this little home offers a wonderful décor, a kitchenette, living room with a sleeper sofa and a bedroom with a king size bed. Relax by the pool under the warm island sun, or take the quick stroll into the Siesta Key Village for the many great shops and restaurants the island has to offer. Walk down the Sunset beach to take in the stunning views and spectacular sun sets. If you feel like venturing off the island, Siesta Key is located just 20 minutes from Sarasota International Airport and just minutes from the downtown area of Sarasota and all it has to offer. Sarasota is the Cultural Gem of the Gulf Coast. It offers numerous galleries, theaters, and some of the finest restaurants in the world. You will not be bored with this location. The list of activities is nearly endless as you can spice up your vacation with bike, kayak, or boat rental for your entertainment. This unit is sure to be a lovely Gulf Holiday for you and your family that will have you returning year after year!brbrBedroom 1 – KingbrLiving Room – Queen Sleeper SofabrbrAdded 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: 23br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $500

One Bed/ One Bath Condo- Step From Siesta Key Beach with Pool On Property!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$314.91

Welcome to our newly renovated two bedroom, one bath, ground floor condo on Siesta Key. Located on the IntraCoastal side there is a waterway on the property. Private access to the beach right across the street. Best of both worlds! Heated pool, tiki bar/grill, and fishing pier on the property. Halfway between Siesta Key Village and the shops at south bridge, restaurants, bars, and stores are easily accessible. The free trolley can take you from one end of the island to the other.brbr- Free wifi is provided in the condo! br- The kitchen is fully equipped with all the essentials including new dishes, pots and pans, coffee maker, toaster, fridge, cookware, glasses, silverware, etc.br- The master bedroom has a king sized bed and dresser.br- The second bedroom has 2 twin beds.br- The living room includes a pull-out queen sofa bed, coffee table, end-tables and flat screen cable tv.br- Sizeable vanity top for bathroom essentialsbr- There are two chairs by the front door to sit back and relax. There is also a private patio at the back of the condo.br - we provide beach chairs, beach umbrellas, beach towels, beach toys for kids and a beach cart to easily carry things to the beach.br- Convenient free parking right outside the front door. Please note trailers or RVs are not allowed.brbr- You have full access to every space in Sea Club II. The club room, swimming pool, fishing pier, tiki bar/grilling areabr- 5 minutes walking to our private beach access across the street.br- Laundry facilities are on-site and are coin or credit card accessible. br- The free trolley takes you from one end of the island to the other.brbrBring your fishing poles as you have the option to fish off our pier.br brIf you are interested in paddle boarding, parasailing, jet-skiing, scootering, you can find nearby rental facilities.br brSiesta Key provides activities during the day as well as a great nightlife with live music, outdoor beach bars and terrific weather year round. Siesta key also provides fabulous restaurant options that you don’t want to miss.

Renovated Siesta Key Condo, beach/heated pool access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$335.83

Escape to Siesta Key and enjoy our cozy ground floor condo, just steps away from a private beach. This fully equipped one-bedroom, one-bath unit comfortably sleeps four with a queen pull-out sofa. Amenities include smart TVsl, on-site laundry, and free assigned parking and Wi-Fi. Perfectly located between Siesta Key Village and the shops at south bridge, with easy access to restaurants, bars, stores, and the free trolley. Book now for a dream vacation on the world-famous Siesta Key Beach! brbr- The kitchen is fully equipped with all the essentials including new dishes, pots and pans, coffee maker, toaster, fridge, cookware, glasses, silverware, etc.br- The bedroom has a king sized bed , dresser and flat screen tv.br- The living room includes a pull-out queen sofa bed, comfortable chairs and flat screen cable tv.br- Sizeable vanity top for bathroom essentialsbr - we provide beach chairs, beach umbrellas, beach towels, a cooler, frozen ice packs, beach toys for kids and a beach cart to easily carry things to the beach.br- Convenient free parking right outside the front door. Please note trailers or RVs are not allowed.br- The condo is on the gulf side a minute's walking to the world famous white sand beach, Chairs/loungers are available at the private beach.br- Convenient ground floor condo, no need to climb stairs.br- Laundry facilities are on-site. br- Access to temperature controlled pool.br- Quiet and safe dead-end street makes it ideal for safety. No through traffic.br-The free trolley takes you from one end of the island to the other.brbrIf you are interested in paddle boarding, parasailing, jet-skiing, scootering, you can find nearby rental facilities.br brSiesta Key provides activities during the day as well as a great nightlife with live music, outdoor beach bars and terrific weather year round. Siesta key also provides fabulous restaurant options that you don’t want to miss.

Newly renovated beachside condo - direct beach access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$462.76

5 Stars for over 15 years on VRBO! Beautiful, quiet, 2 minute walk to the beach!!brMajor renovation complete in January 2020. Brand new kitchen, appliances, tile flooring and fresh new paint. Beautiful Siesta Key Condo at Peppertree Bay. Gulfside unit just a 2 minute walk to the beach and pool. Crescent Beach was voted #2 most beautiful beach in Florida on Travel Channel. You will never run out of exciting things to do! Fishing, exercise room and Tennis Courts on site. Or just relax on the sugar soft sandy beach or go seashell hunting. Beachwalkers paradise, Walk one mile South to the 'Point of Rocks' or head North for a 5 mile round trip beachwalk to the 'Big Pass' on the northern point. Generally a very quiet beach but gets very busy at Spring Break and the July 4th fireworks show. Also Boat Races draw a big crowd for July 4th. FREE WIRELESS INTERNETbrbrKeywords: Beach Home, Island Home, Paradise, Beach House, Walk to the beach, Peppertree, Siesta Key, Crescent Beach,

Siesta Key Gulfside 3BR, 2.5BA Condo, an Island Paradise. steps to the beach.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$220.6

Firethorn unit has 2 bedrooms, one and one half baths, full galley kitchen with all appliances, a breakfast bar, living room w/sleeper, dining room as well as an oversized lanai with a large dining set for open air meals. Large flat screen TV in the living room with high-speed internet included. New washer and Dryer.Kitchen has been updated with granite counters. Updated Baths too.

Firethorn 822 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pool...

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$570.15

Experience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 2-bedroom 2-bathroom home is a must. Inside, this home can sleep up to 4 guests with king beds in each bedroom. This home comes equipped with a full kitchen, a dining area, and a spacious living room for you to enjoy time with your family and friends. Stunning ocean views can be seen from the living room and master bedroom. Watch the spectacular sunsets from one of your multiple balconies located on each floor, or walk out your front door to the sugary white sand of our world-famous beaches. This unit also includes a very convenient outdoor shower and the use of the pool at the Siesta Key Beachside Villas just a block away. Even better still, this unit is only a short stroll into Siesta Key Village, where you can experience many of the wonderful shops and restaurants the island has to offer! This is a truly unique vacation home that you, your family, and friends will truly enjoy, and is sure to be your choice returning year after year!br*This unit is stairs only. All guests must have the ability to use stairsbr*There is no garage parking.brbrBedroom 1: KingbrBedroom 2: KingbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,000

Spacious 2Bed/ 2Bath Beachfront Town Home!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$196.95

Come and enjoy the island lifestyle on Siesta Key in this lovely furnished 3rd floor condo. Enjoy your morning coffee or evening cocktail on the balcony with views of the beautiful inter-coastal waterway from your vacation home. Beach access to Siesta Key’s famous Crescent Beach quartz sand beach is within walking distance. The property is located on lush grounds, amazing community pool, boat basin, tennis courts, pickle ball, basketball, fitness room & BBQ area. Includes the convenience of an in unit washer and dryer and carport. Come and enjoy the Florida lifestyle with breathtaking sunsets, nearby restaurants and entertainment, Siesta Key village & convenient free Siesta Key trolley. Just a short drive over the bridge to the mainland for even more cultural adventures and fun.

Relaxing Siesta Key Condo

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$197.12

Beautifully furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paving stones carports parking, our air-conditioned condo offers two large newly installed wood-like flooring bedrooms with 2 full baths (in-suite master bathroom with new vanity & ceramics), a comfortable living room, fully equipped kitchen with newly installed cabinets & granite counters, dining area, HD cable TV, music entertainment center, Magic Jack telephone system with unlimited calling within the US & Canada and lanai (balcony) with a view of the tropical gardens. All necessary linens are provided, and full-sized coin-operated or App-operated washers and dryers are located downstairs. brNear the intersection of Beach and Midnight Pass Roads in Siesta Key, across (7 -10 minutes walk) from world-renowned Siesta beach, the # 1 beach in the USA & 4th best in the world.brThere is a heated swimming pool, his and hers saunas, two common BBQ areas, club house, private boat docking area, and private covered off the road reserved parking. Free WiFi is available at the condo and pool/clubhouse area. brPlease, see the Condo Virtual Tour in the provided video.brSiesta Key has some 150 stores, galleries, boutiques, salons and specialty shops in Siesta Key village and other locations. There is also a great selection of bars and restaurants. Additionally, downtown Sarasota is a short drive across the north and south key bridges with its renowned shopping, fine dining, and cultural attractions. Free tennis & pickleball courts are steps away from the complex on the way to Siesta beach.brbrThere is a charge for the departure cleaning service and a two week minimum stay policy. brbrOther Amenities include 2 TV's (a 40 in living room with HD cable & a 27 in master bedroom), CD & DVD players, Comcast Xfinity cable TV, dishwasher, microwave, telephone, toaster oven, coffee maker, iron, hair dryers, ceiling fans in living / dining room & master bedroom, beach chairs and umbrellas. Children are welcome (a playpen is available in the 2nd bedroom closet that can serve a young baby up to 2 years old). brbrCoin operated laundry facilities are available in the first floor of the building. You can download the clean cash App on your phone to pay for your laundry for more convenience.brbrOne small dog , 25 lbs or less, is allowed. Assistance dog is allowed with a proof. The management office has the right to reject an over-sized dog.brbrOnce payment is made to the site, Guest Registration Form will be sent to the guests. This form must be completed by the guests, scanned and emailed back to the owners to forward to the Condo Association. Alternatively, guests can send to the owners a clear legible photo of the completed form. Also, a Rental Agreement (Lease) will be sent to the the Guests to sign & return to the owners, together with the complex (WSV) Rules & Regulations.brbrPlease note that for the Winter Months (January - March): Reservations will only be accepted from the 1st or the 15th of the month. Priority for this period will be given to full month(s) rent. As for all seasons reservations, min is 14 days in case full month(s) reservations cannot be secured.brbrA detailed Check-In / Check-Out procedures, together with House & pet rules will be provided to the guests a few weeks before the arrival date.brbrVrbo has a Card on File policy by which guest credit card can be charged for damage, if host submit a claim for damage within 14 days of departure.

2 BR Condo-Short Walk to Siesta Beach/ One 25 lbs Dog Allowed / E. Bird Specials

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$492.98

SerenitybrYour tranquil escape is found at the Serenity Beach Condo at the Beachfront Suites on Siesta Key. Enjoy your peaceful escape to the world-famous Siesta Key Beach, in this lovely 2 bedroom condo on the 2nd floor of the Beachfront Suites on Siesta Key, located directly on the beach. Enjoy your morning coffee on the private balcony as the stress of the world falls from your shoulder and you sink into the calming aesthetic of the Serenity Condo. Complete with everything you need for your special getaway, the Serenity Condo is here to ensure your vacation is here to bring you into a state of Zen.brbrAmenitiesbrImmediate Beach AccessbrAmazing Views of the Gulf of MexicobrFully Stocked KitchenbrPrivate BalconybrHD Smart TV'sbrLarge Shared BackyardbrPicnic AreabrPropane GrillbrOutdoor GamesbrBoard GamesbrBeach Suppliesbr brPet PolicybrThe Dreamview Condo is Dog-Friendly for 1 Dog of 50lbs or fewer pounds or two dogs with a combined weight of 50 pounds. An additional $35/night/pet will be charged as a pet fee. Guests with Pets must sign the Pet Waiver.brbrThe Local Areabr.25 Miles to Siesta Key Public Beachbr.5 Miles to Siesta Key Villagebr5 Miles to Downtown SarasotabrbrThe Beach Front SuitesbrThe Beachfront Suites is a stand-alone tri-plex. The building is three stories with each floor as its own unit. The Serenity Beach Condo is located on the 2nd floor. brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbr**Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking. br**Your inquiry on our property will be responded directly to your personal email. Please keep a lookout for our response so we may best serve your requestbrbrCancellation PolicybrBookings canceled at least 30 days before the start of the stay will receive a 93% refund. Bookings canceled at least 14 days before the start of the stay will receive a 43% refund. Bookings canceled within the 14-day window are non-refundable. brbrReservations of 15 nights or more may be canceled at least 90 days before the start of the stay will receive a 93% refund. Cancellations within 45 days of the check-in date and are refundable up to 43%.brbrShould a refund be issued, a credit to the original credit card in the amount of the reservation minus the cost of the cancellation fees will be issued within 5 to 7 business days.

Apartment

Siesta Key Beach Views – 2BR Oceanfront

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$383.19

When you can't wait to enjoy a well-earned getaway to sunny Siesta Key, make the most of your island adventure by booking Oxford House as your home away from home during your stay. This 2-bed, 2-bath property can welcome up to 7 guests at a time and puts visitors right in the heart of a barrier island experience. Oxford House is surrounded by lush tropical foliage and sits within reach of area attractions and activities too. Booking a stay here provides a refreshing balance between desirable island seclusion and access to fun and exploration when you're looking to discover something new too!brbrInterior AmenitiesbrbrOxford House is designed with space, light, and island-inspired style in mind at every turn. Guests who book a stay will step in to find a spacious open floorplan waiting to greet them paired with large windows throughout to frame a great view too. A fresh color palette incorporates a modern touch while home-inspired furnishings make it simple to settle into luxury starting on day one. The living room in Oxford House hosts an extended and plush beige sofa and matching loveseat settle in front of a sleek black coffee table and large 65-inch television positioned on the far wall of the room. brbrThe living room opens up to the full kitchen where guests can serve up their favorite home-style meal when they aren't dining out across Siesta Key. The kitchen in this home features extended granite countertops, stainless-steel appliances and custom white cabinetry filled with cookware as well. When it's time to enjoy dinner together, guests can gather around the table fit for four guests, the formal table fit for eight, or make the most of additional seating at the breakfast bar. brbrWhen it's time to rest, get a great night's sleep in any of the bedrooms this property features. The master bedroom hosts a king bed and sitting area as well as access to the pool through sliding glass doors. The master also has an en suite bath complete with a stall shower. The second bedroom in the home hosts a queen bed and has easy access to the hall bathroom complete with a shower and tub.brbrExterior FeaturesbrbrFresh-air and outdoor fun is easy to find when you book a stay in Oxford House. This home has its own outdoor shower as well as a private covered pool for enjoying when temperatures are on the rise. Lush greenery surrounds the pool to set a tropical scene while the backyard grill and table set makes for a wonderful place to serve up an alfresco meal or two during your visit.brbrBook TodaybrbrEnjoy your Siesta Key journey in style when you book Oxford House for your next vacation. Reach out to Rent Siesta Key to learn more today!brbrProperty notes:brbrMinimum stay: 1 month minimum reservation required with the exception of 1 week reservations a maximum of 30-days in advance when available. brbrPool Heating: $25/night for less than 3 weeks or $15/night for 3 or more weeks. brbrPets: Pets will be considered for a $200 Non Refundable Fee and must have prior approval from management. Small Dogs will only be considered

Siesta Key vacation rental home close to village with swimming pool and free wifi

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$266.35

*SPECIAL PRICE - Is Listed, subject to change, Hurry! brbr*2026 reopened after our Updatebrkit and baths. Looks the same only newer. Rearranged a little too. You'll love it. brSCROLL-DOWN FOR ---'THE STORY'brbrLOCATION- LOCATION- LOCATION! --- br------IMPORTANT NO TRAFFIC TO BEACH, Village or on/off island. *2mins to the beach and Siesta Village (We've built a successful business over the years and stay booked 95% of the years)br------We offer KITCHEN, BATH, LAUNDRY CONDIMENTS, PAPER GOODS, BEACH SUPPLIES, 4 BIKES, *(things you would have to rent or buy we have available) br------KING, and QUEEN beds. *over-sized bedrooms *upgraded to all-white appliances.br------We'll send you YouTube videos of places to go for fun and restaurants to experience.brbr* br----Join our Frequent Guest List. br....Sat. check in/out br br__'A SIESTA KEY STORY'brFORMER ARCHITECT MODEL HOMEbrA house from the simple KEY life; the way Siesta used to be when it was the BEST KEPT SECRET from all the world. We've maintained its vintage look. The house was architect built and designed around the pool, for that era.br A beautiful story regarding our house, our friend (an Egret) MR. BIRD who visits daily, big tall white bird. He's been visiting our house and the neighbors for years. We once lived here, what's it like to live in paradise. .... SIMPLY BLESSED! VACATION EVERY DAY. With lots of color and large glass doors, windows, the house is on ground level; YOU really connect with the island's nature,... peaceful and charming. And, Our SPECIAL TREE...what a personality, a spreading WATER OAK, wraps around the front and side of the house. You will love it, everyone does.br Great for those who want to experience a true Siesta Key lifestyle, nestled on an oversized lot in a waterfront community, between the Gulf of Mexico waters of Siesta Key Beach and Siesta Village.brbrFROM The OWNERSbr...Our former home, ...is an opportunity to experience what it's like to live on Siesta Key year-round, vacation every day! The sun shines always...we love the openness of the house, like living outside. Once you're on the island you never want to leave....Yes, Island Fever exits!br...MEMORIES FOR A LIFETIME, A PLACE TO CALL HOMEbrbr(SCROLL DOWN FOR FUN AND EXCITEMENT WITHIN A MILE)brbr---We will send you YouTube videos of places to go for fun and restaurants to experience, all on the island and within 5 mi. radius of the island.brFUN AND EXCITEMENT IN THE AREAbrWe will send you YouTubes of what you can do within the area and on a budget!!! WE WANT YOU TO GET EXCITED ABOUT YOUR TRIP!!! WHY WASTE YOUR TIME brbrIT'S A GREAT WAY TO ENJOY THE ISLAND LIFE.brWITHIN A 5 MILE AREA YOU CAN:br....WE HAVE SO MANY EVENTSbr....SATURDAY SUNDAY. FARMERS MARKET IN THE SIESTA KEY VILLAGEbr....STROLL THE VILLAGEbr....RENT A BOATbr....CHARTER FISHINGbr....SCUBA DIVINGbr....PARASAILING ~JET SKIbr....GET YOUR PICTURE TAKEN ON THE BEACH W/FAMILYbr....GET MARRIED OR RENEW YOUR VOWS ON THE BEACH.br....SUNDAY EVE ENJOY THE DRUM CIRCLE AT SIESTA BEACHbrAT THE PUBLIC PAVILLION.br....RIDE THE BIKES AROUND THE ISLAND IT'S A GREAT WAYbrTO ENJOY THE ISLAND LIFE.br....ENJOY FINE DININGbr....GO TO A FABULOUS MALL FOR SHOPPINGbr....5 MILES PLAY GOLF, BOBBY JONES, VERY NICE PUBLICbrCOURSE, there is another one besides this 4 miles awaybr....4 MILES GO DOWNTOWN SARASOTAbr....OPERA, SEVERAL THEATRES, WE ARE BIG ON THE ARTS INbrSARASOTA.brBASEBALL SPRING TRAINING THE BALTIMORE ORIOLES.br....GO TO MARINA JACKS FOR CHARTERED TOURS FABULOUSbrDINING, AND DANCINGbr....VISIT RINGLING MUSEUMbr....WE HAVE BREWERIESbr....JUNGLE GARDENS IS CLOSE BY 5 MILESbr....ART SHOWS, SAND SCULPTURE EVENTS, CHALKbrFESTIVALS. BOAT RACES, BOAT PARADES.br....BUT MOSTLY YOU WILL WANT TO ENJOY THE ISLAND LAIDbrBACK LIFE AND RELAX.br---I WILL BE SENDING YOU YOUTUBES OF WHAT TO DO AND WHERE TO GO.brbrOWNER/MANAGER

#1 SIESTA KEY Beach Glass House w/supplies

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$504.67

The Coral CabanasbrJust 8-steps to path of Siesta Key Beach, world's best beach! 4-minute walk to bars, entertainment, shopping, dining, ice cream and live music of the South Village! Communal lounging, alfresco dining, snorkeling, sunsets, and hammocks. Perfect for families and couples looking to relax, explore and repeat. Book your Siesta Key vacation rental getaway direct now!brbrWhat Guests Lovebr∙ Beaches – 11-step walk to award winning Siesta Key beaches, calm shallow and clearbr∙ Relaxing –secluded spot with hammocks, alfresco-lounging, westerly facing deckbr∙ Reef Snorkeling – 60-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –walk 30-seconds to Siesta Key's best sunsets and whatever comes nextbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 4-min walk to the South Village's live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrSkip the crowds and commercial feel. Coral Cabanas offers Key West-style charm and beach access #13—quieter, more private, and just across the street. With no public parking nearby, this cove is one of Siesta's most exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 7 minutes to Siesta's top eco-adventures—boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe on the balcony, nap in a hammock, or enjoy Siesta's top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise—now add one of the Gulf Coast's best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis property is two stories and this unit is one flight up with no one above it or below it. There is a king bedroom, a bedroom with two double beds and a sleeper sofa. You can sleep up to 7 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, snorkel equipment, and umbrellas. There are also a few paddle boards available on a first come first serve basis and any other gear can be found 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.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.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. 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.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.

Apartment

Gertrude's Siesta | 8-steps to Beach Path! 4-min Dining & Music! Hammocks, Snorkeling, Sunsets!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$290.54

Nestled in a prime location with high-season availability, Condo 210 is the perfect beach retreat, offering 1,220 sq. ft. of space, 2 spacious bedrooms, and 2 luxurious bathrooms. This condo has been upgraded with everything you need for a relaxing and memorable stay.brbrMaster Bedroom Sanctuary: Sleep soundly on the ultra-comfortable king-sized bed. The master suite also features a large, spa-like walk-in shower for a truly relaxing experience.brbrGuest Bedroom Flexibility: The guest room is equipped with a queen bed and en suite bathroom.brbrGourmet Kitchen: The modern, fully-equipped kitchen features top-of-the-line amenities, including a Keurig coffee maker and Ninja blender—perfect for morning coffee or afternoon smoothies.brbrEntertainment Ready: Unwind and enjoy your favorite movies on the 65 smart TV, or take advantage of the condo's beach gear, including towels, linens, beach chairs, and umbrellas—no need to carry anything but your essentials!brbrEndless Beach Fun: Simply pack your swimsuit, sunglasses, sunscreen, and flip-flops, and you’re ready for a day of sunbathing and sandcastle-building on the world-famous Siesta Key Beach. After a day in the sun, relax with a glass of wine on the screened-in lanai while watching breathtakingbrbrThis condo is the ultimate beach vacation dream come true. Book now and make it a reality!

Sunsets and Sand 2 Bed 2 Bath Siesta Key Beach with Full Gulf Views

Siesta Key, Florida, United States

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Bath

Sleeps

$1450.72

Located on Siesta Key on a dead end street is our 4 bedroom 3 bath home spacious enough for a large family gathering. brbrSituated on the Grand Canal with the world famous beach close by, it’s easy to take the free community shuttle, take a short bike ride or even walk if you prefer.brbrOur home has everything you need for a relaxing and fun filled holiday. brbrFamilies find our home works very well as it is large enough for everyone to find their special spot. br

Siesta Key Retreat Sarasota Florida

Siesta Key, Florida, United States

4

Bed

3

Bath

12

Sleeps

$349.59

Welcome to The Salt Life.brbrStay in the heart of Siesta Key ; just 100 yards to the beach and 2 blocks to Siesta Key Village. This newly renovated, family-owned+ managed coastal retreat offers the rare combination of walkability, comfort, and personal hosting. Enjoy the beach, sunsets, heated pool, restaurants, and live music ; all on foot.brbrWe are experienced Superhosts with 300+ five-star reviews at our other property. Our commitment to experience, personal touches and detail set us apart.

Villa

100 Yds to Beach+2 Blocks to Siesta Key Village ; Heated Pool

Siesta Key, Florida, United States

1

Bed

1

Bath

4

Sleeps

$292.24

SIESTA KEY IS CALLING! LOOKING TO ESCAPE THE COLD WEATHER THIS WINTER!!! brbrLOCATIONLOCATION,LOCATION!!! We have an amazing fully equipped condo with monthly rentals in Siesta Key, FL. Perfect for boating and beach lovers. This 2 bedroom, 2 bath first floor condo with a one car garage on Siesta Key will fulfill all your dreams! Spend the day on the famous Siesta Key Beach (just steps away from the #1 beach in the USA) with our beach chairs and cart and come back and enjoy the fish jumping from your personal lanai! This unit is located in a gated community in the heart of Siesta Key! The trolley stop is also in front of the complex which will take you to both villages or downtown Sarasota. Play tennis/pickle ball on the private courts, lounge by the heated pool or fish out your back door.brbrYou will need to provide information to the association for a basic background check prior to accessing this rental, this includes vehicle details. A short phone call may be required with the association to acquaint you with the property.

Waterfront 2-bedroom condo across from the beautiful Siesta Key Beach with AC

Siesta Key, Florida, United States

2

Bed

2

Bath

6

Sleeps

$458.78

Luxury Siesta Key Retreat – 5 Bedrooms | Walk to the Beach | Game Room | Bikes IncludedbrbrExperience the best of Siesta Key from this stunning 5-bedroom, 5-bathroom coastal retreat, perfectly designed for families and groups looking for space, comfort, and unforgettable beach memories.brbrLocated within walking distance to the world-famous Siesta Key Beach, you can start your mornings with a peaceful stroll to the powder-white sand and end your evenings watching the breathtaking Gulf Coast sunsets.brbrStep inside to a bright and welcoming home where modern comfort meets relaxed island living. The spacious layout offers multiple gathering areas perfect for entertaining, relaxing after the beach, or enjoying quality time with family and friends.brbrEach bedroom is thoughtfully designed to provide a peaceful and private escape, while the five full bathrooms ensure everyone has plenty of space to get ready for the day or unwind after sunset. The bathrooms feature spa-like showers with luxurious rainfall showerheads, creating a relaxing retreat after a long day in the sun.brbrKids and adults alike will love the dedicated game room with arcade games, making it the perfect spot for entertainment, laughter, and friendly competition.brbrFor exploring the island, bikes are included, making it easy to cruise around Siesta Key, ride to the beach, or explore the nearby restaurants and shops in Siesta Key Village.brbrAfter a day at the beach, rinse off in the convenient outdoor shower, then relax in the tranquil atmosphere of your private retreat.brbrWhether you're planning a family vacation, group getaway, or special celebration, this home offers the perfect balance of location, comfort, luxury, and fun.brbrCome experience the magic of Siesta Key living — where unforgettable memories are made.

#1 Beach House Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$235.71

Summary:brbrUpdated 1 bedroom, 2nd Floor unit in Siesta Village offers great location just two buildings from the beach and 1 block into the village with restaurants and shopping. Peek-a-boo Gulf view from front porch. The unit offers tile floors, leather furniture, updated kitchen and TVs in living room and bedroom. Complex offers community pool and laundry facilities located just off common area. WIFI. Parking for 1 car. Sleeps 4 (1 King, 1 sleeper). 1-week minimum.

Apartment

Gulf Holiday 16 Siesta Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$282.63