Vacation Rentals By Owner In Siesta Key, FL

Experience the Gulf breezes and partial views with this lovely 2-bedrom, 1-bathroom home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this home features a king bed in the master, a queen in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the second floor, is right outside of the Siesta Key Village, making it a breeze to walk to many of the restaurants, shops, and live entertainment the island has to offer. Relax in the sugary white sand or swim in the crystal-clear waters. Enjoy the brilliant colors of sunset at this beautiful vacation home that will have you coming back year after year!br*Stairs only. All guests must have the ability to climb stairs.br*No garage parking.brbrBedroom 1: KingbrBedroom 2: QueenbrLiving Area: Queen Sofa SleeperbrbrAdded 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*Pets are allowed, dogs only. Our pet fee is $39 per day/ per pet. Restrictions may apply on weight and breed, please check when making reservation.brbr*Unit is on the second floors, must be able to climb stairs.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

Apartment

A Beautiful 2 Bed/1 Bath for Living the Dream Steps from Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$311.33

Our House at the Beach C-121brCondo in Siesta Key, FLbrbrOur House at the Beach is located directly across the street from Siesta Key Beach, home to mesmerizing white sands and unforgettable Florida sunsets. This complex is set around a scenic lake and features a private community pool, a covered pavilion area with a BBQ, a picnic area, and two tennis courts for guests to enjoy. brbrHighlightsbr• Across the street from Siesta Key Beachbr• Shared Poolbr• Two Tennis Courtsbr• Shared BBQ areabr• Private washer and dryerbrbrThis beautiful and very private townhome unit includes a fully equipped kitchen with cooking essentials and a modern kitchen table. It allows for easy guest access with few stairs upon entry and inside, and with no unit above it will ensure your stay is quiet and relaxing. After fun-filled days spent in the Florida sunshine, relax on the large sectional couch or on the balcony that boasts water views and has comfy seating. The primary bedroom has a King bed, a spacious walk-in closet, and an ensuite bathroom with a walk-in shower. In the guest bedroom is a Queen bed; in the hallway bathroom is a shower and tub combination. The condo has a washer and dryer, so your beach towels are always fresh! Pack your bags for a great vacation at Our House at the Beach!

Near Beach! Shared Pool and Tennis Court- Our House at the Beach C-121

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$250.58

Jamaica Royale Unit 046 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit 046, a newly remodeled 1-bedroom, 1-bath villa located in the heart of Siesta Key and Crescent Beach and just a 5-minute walk from the world-renowned Siesta Beach. Managed by Tropical Sands Accommodations, this stylish ground-level unit is ideal for couples or small families looking for a relaxing island retreat with the convenience of community amenities and an unbeatable location.brbrHighlights:br• 5-minute walk to Siesta Beachbr• 1 Bedroom / 1 Bathroombr• Beds: 2 Queens, 1 Queen Sleeper Sofabr• Private Beach Access within gated communitybr• 3 Shared Heated Poolsbr• Community Shuffleboard Courtbr• Shared BBQ Grills and Picnic Areasbr• Onsite Laundry Facilitiesbr• 1 Assigned Parking Spacebr• Close to Siesta Key Village dining and shoppingbrbrEnjoy laid-back island living with updated interiors and easy access to everything Siesta Key has to offer. Step outside your door and you’ll find a shared heated pool just steps from the villa, along with community shuffleboard courts, a grilling area, and pickleball courts within walking distance of the complex. Whether you’re cooling off after a beach day, grilling up a casual dinner, or enjoying a friendly game in the sunshine, you’ll love the convenience of these resort-style amenities just moments from your door.brbrThe welcoming living area features a plush sofa (with queen sleeper), flat-screen TV, and bright coastal decor designed to help you unwind. The open layout makes it easy to relax, entertain, or simply enjoy a quiet evening indoors. With complimentary Wi-Fi, air conditioning, and a washer and dryer, everything you need for a carefree vacation is at your fingertips.brbrThe fully equipped kitchen includes a full-size refrigerator, stove, oven, microwave, dishwasher, toaster, and a drip coffee maker—perfect for brewing your morning cup before heading to the beach. The kitchen island will offer stools for you and your family to enjoy meals or plan your next adventure.brThe spacious primary bedroom features two comfortable Queen-sized beds, ample closet space, and easy access to the hallway bathroom. The full bath includes a walk-in shower, and an additional half bath adds extra convenience, especially for guests using the sleeper sofa in the living area.brbrRoom Detailsbr• Primary Bedroom – Two Queen bedsbr• Bathroom – Full hallway bath with walk-in showerbr• Living Room – Queen sleeper sofabrbrLocated in the well-loved Jamaica Royale community, this villa offers easy beach access, a family-friendly atmosphere, and all the comforts of home. Guests will enjoy walkable proximity to shops, dining, and the white quartz sands of Siesta Key Beach, consistently ranked among the best beaches in the United States. This property requires a 7-night minimum stay, giving you plenty of time to unwind, explore the island, and experience the laid-back charm of Siesta Key.

Jamaica Royale 046: Completely renovated 1 bed 1 bath in paradise! Sleeps 4.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$633.32

This is the one you have been waiting for! Located 4 blocks to Siesta Key village and a short ride to the beach in a golf cart/Bike. Be ready for the WOW factor as soon as you walk through the door. This beautiful 3 bed 2 bathroom heated salt water pool home has been completely remodeled from top to bottom. 3 entertaining lanai spaces that provides grilling, relaxation & plenty of privacy with enclosed fence around property. All you need is your suitcases and flipflops to enjoy the beach life.brbrWe are very blessed and our home is on higher ground level the hurricanes didn’t affect us. We are able to take bookings, our calendar is updated. The beach is gorgeous. Most restaurants are open and the village is back to normal! We are ready for our guests. brbrThe entire home has the Florida beach charm you are looking for. A beautiful salt water pool that is heated the entire winter. The Main bedroom has a king bed with a full bathroom right next to it. You will find another bedroom with a queen bed. Out by the front porch is the 3rd bedroom with a full bed that has its own private full bathroom as well. The home has a full kitchen, laundry area, dining and living area. Large accordion glass doors open up to the outdoor dining area & pool. Beach chairs, cooler, beach buggy & Beach towels are provided. A pack n play and highchair is at the home too! The entire property is fenced in and the Blackstone grill is a grillmaster's delight.brbrA few beach cruisers/bicycles are available for your use. A 10 min walk to the village for all the restaurants, nightlife and shopping.

Heated Saltwater Pool, Walk to Siesta Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$188.94

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.brPlease note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.brOur condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!brOur unit has an assigned carport. brWhy just go to Florida when you can visit the #1 Beach in the USA! White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking while staying here at White Sands Village.brbrSiesta Beach: Rated 2021 #1 beach in Florida by Holidu https://www.bizjournals.com/tampabay/news/2021/06/23/siesta-key-beach-named-no-1-beach-in-the-state.html, 2020 Tripadvisor #1 beach in the USA https://www.sarasotamagazine.com/news-and-profiles/2020/08/siesta-key-beach-named-no-1-in-the-country-again-tripadvisor , Dr Beach 2017 #1 beach in the USA https://www.drbeach.org/2017-siesta-beach-sarasota-floridabrbrWe welcome your pet, ( NO CATS) but White Sands has a STRICTLY ENFORCED 1 PET/25# MAXIMUM WEIGHT RULE. Please respect this and avoid problems when you arrive. See our Pet Rules below.brbrThe condo is NOT ADA ACCESSIBLE. NO SMOKING.brbrThe first sign that White Sands Village is the right place for you are the grounds, seven acres beautifully landscaped with palm trees, live oaks, flowering shrubs and tropical flowers.brOur pool is heated year-round to a warm 86º, so you can enjoy a swim even during the cooler months. Catch a bit of sun on a lounge chair, or sit in the shade and enjoy a bit of vacation reading.brPublic tennis/pickleball courts are just across the street.brFour lighted gas grills, on the White Sands property, are available for your use.brOne covered parking space is provided for each unit, with additional parking available.brLaundry facilities are available at four locations.brLinens are supplied and kitchens are fully equipped in each of our one- and two-bedroom rental units.brSit by the peaceful lagoon connected to the Intracoastal Waterway.brIn addition to the stunning Siesta Key Public Beach, there are two additional Gulf of Mexico beaches on Siesta Key, as well as great little shops and restaurants. You’ve got easy access to boat rentals, jet ski rentals, parasailing…recreation awaits you!brCrescent Beach, just south of the public beach, is a quieter and more private beach, with only one public access road. Its southern tip is the Point of Rocks, a great snorkeling and diving area with coral reefs that often harbor abundant marine life.brTurtle Beach, south of Crescent Beach, is a great family play area, with a playground, horseshoe pit, boat launch, volleyball court and picnic tables. It’s also a good place for finding shells and perhaps some shark teeth. Here you can launch your boat, fish in Blind Pass Lagoon, or eat in a nearby restaurant.brSiesta Key Village is full of shops and restaurants. You can buy just about everything you need to enjoy your beach vacation, including beachwear, sun products, and toys. There are also little boutique shops where you can indulge your love of unique clothing, jewelry, flowers and scented lotions. Several local restaurants offer patio dining, which you can enjoy from breakfast spots to dinner and evening entertainment.brCURRENT PET RULES AS OF 6/23/2022brPETS ARE ONLY ALLOWED IN UNITS SPECIFICALLY ALLOWING PETS.brPets at White Sands Village are limited to one dog of less than 25 lbs. or one cat and only when they are not maintained or bred for any commercial purpose and when proper restraint and control are used in keeping them. brDogs and cats must be either leashed or carried and must be exercised and curbed only in one of the two marked pet areas, along the street side of White Sands Village. Please walk DIRECTLY to one of those areas by way of the driveways. Dogs and cats are prohibited from, courtyards, courtyard sidewalks, grassed areas and fenced pool areas, except the two pet areas noted above. brAll pet waste must be picked up, bagged and placed in the designated pet waste stations in the pet walk areas. Please do not use waste cans in condos, laundries, grill areas or by the pool, for pet waste

Newly Renovated 2 Bed/2 Bath 1st floor. Htd Pool, Wifi, 0.25 mi to Siesta Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$544.9

Newly renovated gated beach access apartment with a pool. This is a four bedroom and two bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated section of the Siesta Key beach that only residents on this street have access too.brbrThe house was completely updated and has all new furniture, sheets, pillows, towels, etc. The pool area was just upgraded with new pool/deck furniture.brbrAmenities Included:br- Private pool for guests only at our quadplexbr- Key fobs to the gated beach only a short walk to the beachbr- New sheets, towels, pillows, comforters, etc.br- Soap and shampoobr- Roku TV, able to login to all of your different streaming servicesbr- Netflix subscription included at the housebr- Beach chairs and toysbr- Super fast internet/wifibr- Washer and dryerbr- Full size kitchen with all the essentials and a Keurig machinebr- Gas powered grillbr- Lots of outdoor seating by pool and patiobrbrThis property sleeps up to 10 guests. There is a king bed in the master bedroom. A queen bed and two XL singles (as long as a queen, easier for adults to fit in) in the bedroom next to the master. In the two bedrooms by the front door there are two XL singles in the one and a full size bed in the other. The living room has a pullout queen sofa bed.brbrGreat entertaining place with lots of space! Great for family's, large groups of friends, company trips, or whatever it may be where you need a lot of space and beds. The open floor plan lets you really enjoy the whole space. The large living room has lots of seating with our brand new furniture. There is lots of natural lighting shining into the open floor plan through the large glass doors that overlook the pool.brbrProperty Rules:br- No parties are allowed. br- No pets allowed.br- Quiet hours are after 10:00 pm and until 7:00 am. This is to respect the other guests in the other apartments. Loud noise between these times is not allowed.br- As a disclosure there are security cameras located on the outside of the property. They are there for your security. They are only on the outside of the property.br- There must be someone aged 25 years or older present at all times that is apart of your group that is staying in our apartment. br- You must also report in your reservation the accurate amount of guests that will be staying in the unit. br- You are not allowed to have any guests come that are not registered as part of your reservation without the written consent of the owner/manager.br- No more then the maximum amount of guests are allowed to book this apartment without the written consent of the owner/manager.

Newly Renovated Large 4BR w/ Pool - Walk to Gated beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1886.03

Summary:brbrIsland House is a 7BR/6BA Siesta Key retreat just a 4-minute walk to the beach ️. Enjoy a private pool with waterslide, hot tub, BBQ area, and separate guest suite. With king bedrooms, bunk rooms, pet-friendly options, and walkable access to Siesta Key Village dining and shops, this home is perfect for unforgettable family vacations ✨brbrbrbrThe Space:brbr Island House – Your Private Siesta Key Oasis brbr 344 Canal Rd, Siesta Key, FL 34242brbrbrbrWelcome to Island House, a spacious and family-friendly 7-bedroom, 6-bathroom retreat just a 4-minute walk to world-famous Siesta Beach ️. Designed for unforgettable group getaways, this coastal escape features a private pool with waterslide, relaxing hot tub, and a separate guest suite—perfect for multi-family vacations or traveling with grandparents.brbrbrbrAfter a day at the beach, retreat to your private backyard paradise . Splash into the sparkling pool, race down the waterslide, rinse off in the outdoor shower, then gather around the grill for alfresco dinners under the island sky . Inside, the open living space invites everyone to relax together, while the fully equipped kitchen with coastal finishes makes meal prep a breeze.brbrbrbrWith thoughtful sleeping arrangements, plenty of space to spread out, and a walkable location near Siesta Key Village’s shops and dining, Island House delivers the perfect blend of comfort, convenience, and island fun .brbrbrbr✨ Highlights ✨brbrbrbr• ️ 4-minute walk to Siesta Beachbrbr• Private pool, hot tub & waterslidebrbr• Pet-friendly (host approval & fee)brbr• BBQ grill & outdoor diningbrbr• Outdoor showerbrbr• Separate private guest suitebrbr• ️ Walk to Siesta Key Villagebrbr• ️ Sleeps a crowd comfortablybrbr• 4 parking spacesbrbr• Washer & dryerbrbr• ️ Professional linen programbrbrbrbr Bedrooms & Sleeping Arrangements brbrbrbr• Primary Bedroom (2nd Floor): King bed, ensuite bath with shower/tub combobrbr• Second Bedroom (2nd Floor): King bed, ensuite bath with shower/tub combobrbr• Third Bedroom (2nd Floor): King bed, ensuite bath with walk-in showerbrbr• Fourth Bedroom (2nd Floor): Twin-over-twin bunk with twin trundle, ensuite bathbrbr• Fifth Bedroom (2nd Floor): Full-over-full bunk bedbrbr• Sixth Bedroom (1st Floor): King bed, shared hall bath with walk-in showerbrbr• Seventh Bedroom – Private Suite: King bed, TV, mini fridge, ensuite bath with shower/tub combobrbrbrbrAdditional Sleeping:brbr• Living Room: Full sleeper sofabrbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 4 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

Island House – Walk to Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$713.52

Just a five-minute walk across Beach Road to Siesta Key's world-famous beach! This fifth floor 2bd/2ba corner unit offers an abundance of sunlight with views of the crystal white sands of Siesta Key Beach. The condo also includes two balconies that add significant space for watching the sunrise while sipping your morning coffee or enjoying a glass of wine while catching a beautiful sunset. The condo has an open floor plan which includes a kitchen, with all the conveniences of home, seating for six in the living room and dining room. The master bedroom has a king bed with an ensuite bathroom. The second bedroom has two twin beds. All linens, bath, beach and pool towels are included. A full-size washer and dryer are also available in the unit. High speed wireless internet and satellite TV complement this space. If a beach day is not on the agenda, you can enjoy the heated swimming pool, play tennis or pickleball on one of the two courts or just relax in the comfort of a chaise lounge on the pool deck. A BBQ grill and covered picnic area are also located in the communal pool area. Beach chairs, umbrella and toys are also provided in the unit. Assigned covered parking. Siesta Key Village is just a short ride away on the FREE trolley that will pick up and drop you off right outside of the condo. If you are interested in getting some exercise, it is about a 20-minute walk to the village. The village offers restaurants, shops and plenty to do during the day or evening. This is a smoke free and pet free property.brKitchen includes: blender, toaster, K cup and full-size coffee maker, ice maker, microwave oven.brAdditional amenities: hair dryers, assorted beach chairs, boogie board, tennis racquets, pool noodles and misc. beach toys.

AMAZING VIEWS of Siesta Key Beach and Gulf. Unit 502W. Fifth floor corner unit.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$578.27

Sunset West - Private Pool, Spa, Near Siesta Key Beach & Siesta Key Villagebrbr✨ Why You'll Love This HomebrWelcome to your private Siesta Key retreat—just minutes from vibrant Siesta Key Village. Sunset West invites you to unwind with your own heated pool, in-ground spa, and lush backyard oasis designed for effortless island living.brbr ‍ ‍ Perfect ForbrCouples, families, or small groups looking for a private, walkable island escape with easy beach access.brbr ️ Imagine ThisbrStart your day with coffee on the poolside patio, surrounded by tropical greenery and the gentle sound of palm fronds swaying overhead. After a morning in the sand, cool off in your private heated pool or unwind in the spa. In the afternoon, challenge your friends to a quick round on the three-hole putt-putt green, then gather around the grill for lunch al fresco. As the sun dips low, mix drinks at the built-in bar, and settle into the open living space for a movie or a quiet evening.brbr Where You'll Sleepbr Bedroom 1: King bed, ensuite bath with double vanity & walk-in shower, French doors to patio, TVbr Bedroom 2: King bed, ensuite bath with walk-in shower, TVbr Bedroom 3: Queen bed, shared hall bath, TVbr Bedroom 4: Two twin-over-twin bunk beds, shared hall bathbrbr Explore the Areabr • 2-minute walk to the free Siesta Key trolley stopbr • 2 miles to Siesta Key Village — boutiques, coffee shops, dining, live musicbr • 3.1 miles to Siesta Key Public Beach accessbr • 1.6 miles to Shakespeare's Gastropubbr • 4.8 miles to The Palms Golf ClubbrbrWhether you're after beach days, dining, shopping, or exploring the island by bike or golf cart, Sunset West places you within easy reach.brbr Don't wait—this Siesta Key escape books quickly. Your stay includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr⚠️ Need to Know: The pool and spa are heated between November 15 – April 15. We provide starter packs of kitchen and toiletry essentials - making your first couple of nights seamless. Free high speed WiFi. This property is registered as a vacation rental with the City of Sarasota with Registration Number VR25-00197. Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and has a maximum occupancy of 10 guests.

Sunset West | Private Pool, Spa, Near Siesta Key Beach & Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$241.86

brEnjoy the Spacious Luxury - This welcoming and spacious townhouse-style condominium is located on the 8 mile-long barrier island of Siesta Key across from Siesta Key's world-famous beach! The townhome offers easy access to the widest expanse of beach on Siesta Key and public beach amenities. And when you are ready to retreat to your own space, you have your privacy with this property as it is nestled by Florida foliage. This townhome puts you right there by the beach without compromising your privacy. brProfessionally managed by an onsite licensed realtor, this townhome offers a generously 1352 SQFT bi-level layout that has been designed with Florida elegance and comfort in mind. The condo can accommodate a maximum of 6 guests (inclusive of children). This well-appointed condominium with 10ft ceilings and generous size rooms is one of the best places to stay on Siesta Key. brThis condominium development includes a private pool, covered pavilion area with a barbecue grill, a picnic area and tennis courts. There is no better way to enjoy Florida then to stay at our townhome on Siesta Key. brbrWHY THIS TOWNHOME - Stay in this townhome and start the morning right with a cup of coffee on the lake side balcony furnished with generous and comfortable patio chair and ottoman sets. Enjoy lunch in the eat-in kitchen, which is fully stocked with pots, pans, dishware, flatware, dishwasher, refrigerator, stove and microwave. The unit also includes a full side-by-side washer and dryer set for your convenience. The 10 ft ceilings in the spacious great room invite in the Florida sunshine and make the room a wonderful gathering place. A 50 flat panel TV and generous seating is a comfortable way to relax after sunset. A queen-size sleeper couch sits adjacent to the conversation area in the great room. The expansive balcony overlooking the grounds is accessible from both the living room and master bedroom suite. The spacious master bedroom offers 10ft ceilings, a king bed and an ensuite bathroom with closets and dressing area. The unit has a full second bathroom that is adjacent to the guest bedroom furnished with a queen bed. Dine-in at an expansive dining table that comfortably accommodates 6. This townhouse offers ample closets and storage space, high-speed Internet, WI-FI, telephone, cable TV in the living room and each bedroom, as well as garage parking for a single vehicle. brbrbrWhether it's a vacation or a “flexcation near the Florida beach this property is perfect. brIf you can work from anywhere - why not work from sunny Florida and get some Vitamin D This raised first floor townhouse style condominium has a 6ft deep balcony with WIFI reaches out to the balcony so you can stay connected while you enjoy the warm Florida weather. There is also WIFI available at the condominium complex's community pool. brbrSIESTA KEY PUBLIC BEACH - Location, location, location -This townhome is located directly across from Siesta Key's beautiful public beach, making a walk on the sugar sand beach and a splash in the ocean a breeze. Siesta Key beach is world-renown for the 99% quartz sand – sand with the consistency and feel of powder sugar. Dr. Beach has again elected to promote Siesta Key beach as one of the best beaches in the USA for 2016 and 2017!! And the beach continues to be amazing right now! Siesta Key's public beach is the most expansive beach on the key with no properties beach-side along the public areas of this beach. Siesta Key Public beach is the only beach on Siesta Key with life guard stations, outdoor showers to rinse off the sand, picnic areas, playgrounds, sand volleyball courts, beach house with restaurant and restrooms and adjacent tennis courts. Siesta Key offers the world's most amazing sand along gentle Golf waters and this property puts you right there. brbrONSITE PROPERTY MANAGER & CONCIERGE SERVICES The property is professionally managed, so that your Siesta Key vacation is not one that you will soon forget. The onsite property manager offers guests services so you enjoy a vacation experience that is worth repeating.brbrThis rental includes RENTAL DAMAGE insurance from VRBO-HomeAwaybrbrTRANSPORTATION brSIESTA KEY BREEZE TROLLEY is free and operates Monday through Sunday 8am to Midnight on Siesta Key brSiesta Key has numerous shuttle services that provide island transport to visitors - these transport company personnel provide transport for cash tips

Luxury condo steps away from Siesta Key public beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1547.43

Experience the breathtaking views of this beachfront home! Located directly on Sunset Beach on Siesta Key, this 5-bedroom 4-bathroom home is a must. Inside, this home is beautifully decorated and can comfortably sleep up to 14 guests. 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. 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! With views like this, this vacation home 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 – King brBedroom 3 – King brBedroom 4 – King brBedroom 5 – Full Bunk BedbrLiving Room- 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: 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: $1,500

Beautiful 5 Bedroom Home Directly on Siesta Key Beach!!

Siesta Key, Florida, United States

5

Bed

Bath

14

Sleeps

$439.14

Summary:brThe Anchorage Resort on Siesta Key - includes resort amenity access Our 2 bedroom 2 bathroom private vacation condo is a great option for anyone wanting a home base to enjoy the best of all that Siesta Key has to offer Anchorage Resort Condo 2 bedrooms 2 bathrooms Sixth Floor Condo with balcony overlooks Southern Siesta Key Fully equipped Kitchen with seating for 4 at the dining table and 4 at kitchen island Beach Supplies include- Chairs Umbrella Cooler Raft Float Items Beach Towels Community Pool- Largest pool on the Key Gated Community Siesta Key Trolley- free pickup in front of the resort entrance Private Beach access to Crescent Beach across the street ElevatorBEDROOMS Sixth Floor Condo Bedroom 1 One King Bed Ensuite Bathroom Balcony Access 55 Smart TVBedroom 2 Two Queen Beds Balcony Access 50 Smart TVThe Anchorage Resort Amenity Access Included with Rental Olympic-Size Pool 3 Lighted Tennis Pickleball Courts Out of Order Shuffleboard Community BBQ area Individual Picnic areas along the Canal Intracoastal Waterway Exercise Room His and Hers Saunas Bike Kayak Racks subject to availability Boat Dock Seawall- Kayak Launch Closed Coin-Operated Washer Dryer on Each FloorPool Information - Community Pool- Heated Resort Parking Rules The resort allows a maximum of 2 cars Vehicles must be registered with the front office during office hoursHOA Rules Lead guest must be age 25 or older ID is checked upon registration at the resort No petsJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday only Distances from Resort to Shopping Attractions Daiquiri Deck South Siesta Key- 5-minute walk across the street Crescent Beach Private Beach Access- 7-minute walk across the street Toasted Mango Cafe - 9-minute walk Siesta Key Watersports - 6 mile Siesta Key Village- 2 7 trolley stop Publix at Sarasota Pavilion- 1 4 miles Marie Selby Botanical Gardens - 6 miles Sarasota Bradenton Airport SRQ - 11 miles Why Choose this Rental - Professionally managed to serve all your needs- Management company has over 26 years of experience hosting well over 200 000 families- Go straight to your rental with online email check-in- 24 7 on-call maintenance- Free On-Site Parking- Smoke-free and pet-free for your comfort- Towels and linens are provided- Complimentary WiFi Our Starter Welcome packet supplies - 2 rolls toilet paper per bathroom- 1 hotel-size bar soap per bathroom- 1 hotel-size shampoo conditioner per full bathroom- 1 roll paper towel- 2 packet dishwasher detergent- Size 13-gallon Trash bagsAny supplies beyond this are up to the guest to replenish we do not restock these items This is an industry-standard practice FOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS this does not apply if you are staying less than 30 nights We will collect a 1 500 deposit Balance is due 60 days prior to arrivalIf canceled 90 days or more before arrival we keep with us 250 00 1 250 00 will be refunded If canceled between 61 and 89 days prior to arrival we keep with us the 1 500 00 deposit No cancellation or modification 60 days or less prior to arrival

ANC605

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$426.1

Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath fully furnished Gulf Front vacation rentals on award winning Crescent Beach. Siesta Key is famous for beautiful turquoise water full of sea life and white powdery crystal sand beaches. Enjoy all our unique features with the convenience of being steps from our own private beach or relax in one of our two heated swimming pools.brbrEach room has lanai access and expansive beachfront views from the living room and both bedrooms. You can enjoy waking up to a fresh cup of coffee as you listen to waves roll in from offshore or unwind at the end of each day sipping your favorite glass of wine as the sun sets in the Gulf of Mexico. You will never miss a sunset! Indulge from the comfort of your own condo!brbrOur Accommodations are just 2 miles from the popular Siesta Key Village with shops, restaurants, bars, coffee shops and more or a short walk to nearby restaurants, convenience stores, and water sports rentals!brbrIf you are looking for a family vacation or a romantic getaway Crystal Sands is the perfect place for you. Come stay with us at the most exclusive resort on Siesta Key that offers the best beachfront views on the island!

Crystal Sands Tower Unit 1008 - Beachfront

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1433.04

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beachbrbr Why You'll Love This HomebrLet the laid-back rhythm of island life wash over you at Siesta Soul—just a 3-minute walk to both Siesta Key Beach and the lively Village. From the lush backyard retreat with a heated pool and fire table to the stylish coastal interiors, this home blends comfort, convenience, and charm. Whether you're chasing sunsets, exploring local eats, or lounging poolside, every moment here feels effortless.brbr ‍ ‍ Perfect ForbrFamilies or friend groups seeking walkability, privacy, and a true Siesta Key experience just steps from the action.brbr ️ Imagine ThisbrYou wake up to soft morning light and the sound of palms swaying outside your window. Coffee brews in the open kitchen as the house slowly comes to life. Later, you wander just minutes to the powdery sands of Siesta Key Beach or stroll into the Village for brunch and boutique shopping. By afternoon, you're back in your own private oasis—dipping into the heated pool, rinsing off in the outdoor shower, and unwinding beneath the screened balcony with a chilled drink in hand. As the sun sets, you gather around the fire table, the night warm and alive with laughter, stories, and the magic of island time.brbr Where You'll Sleepbr• Bedroom 1: Queen Bed, Shared Bath, Mid Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Mid Floor, TVbr• Bedroom 3: King Bed, Ensuite Bath, Upper Floor, TVbr• Bedroom 4: Full Bed, Shared Bath, Upper Floor, TVbrbr Explore the Areabr• 0.2 Miles (3-Minute Walk) to Siesta Key Village – Dining, Nightlife & Shopsbr• 0.2 Miles (3-Minute Walk) to Siesta Key Beach – White Quartz Sand & Turquoise Waterbr• Easy Access to Bike Rentals, Paddle Boards, and Local Excursionsbr• Surrounded by Local Cafés, Fresh Seafood, and Live Music Venuesbr• Sunset Views and Beach Walks Right at Your Doorstepbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need To Know: The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.. This home has stairs. If any member of your party has difficulty with stairs, please contact us to discuss alternative accommodations.

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

Siesta Key, Florida, United States

Bed

3

Bath

8

Sleeps

$389.71

Dos Casitas Retreat by Siesta Key Luxury Rental PropertiesbrbrWelcome to Dos Casitas Retreat, a charming four-bedroom, two-bath duplex tucked along beautiful Siesta Key. Ideal for families or friends traveling together, this coastal hideaway offers the perfect balance of comfort and convenience with two side by side homes. With Casita East and Casita West, each with its own private entrance, living area, and kitchen. Located just minutes from Siesta Key Beach and the vibrant Siesta Key Village, guests can enjoy sun-soaked days on the sand followed by evenings exploring local shops, restaurants, and live entertainment.brbrHighlightsbr• 4 Bedrooms / 2 Bathrooms (Each side = 2 bedrooms / 1 bath)br• 2 Queen beds and 4 Twin bedsbr• Private duplex rented togetherbr• Short walk or drive to Siesta Key Beachbr• Close to Siesta Key Village dining and shoppingbr• Outdoor patio and grill areabr• Beach chairs and essentials includedbr• Washer and dryer in each unitbr• Complimentary Wi-Fi and cable TVbr• Pet friendly with host approval br• On-site parking availablebrbrDos Casitas Retreat combines the comfort of home with the laid back charm of island living. Each side of this duplex features a cozy outdoor patio where you can sip morning coffee beneath swaying palms or unwind with evening cocktails after a day on the beach. The shared yard includes a grill and seating area perfect for casual meals in the coastal breeze. With two full kitchens and two living spaces, guests traveling together can enjoy time as a group while still having their own private retreats.brbrBoth Casita East and Casita West feature bright, open living rooms furnished with plush sofas and flat-screen TVs for relaxing movie nights. The fully equipped kitchens include everything you need for effortless meal prep. From modern appliances, cookware, and dining space for family meals or quick snacks before heading to the shore. The interiors are tastefully decorated with coastal accents that reflect Siesta Key’s relaxed, upscale atmosphere.brbrEach side of Dos Casitas Retreat offers two inviting bedrooms and one full bathroom. The primary bedrooms feature queen-sized beds, soft linens, and storage space for extended stays. The guest rooms include two twin beds, ideal for children or additional guests. Bathrooms are clean and well appointed with shower/tub combinations, plush towels, and bright, beachy decor.brbrIf you’re traveling with a larger group, renting both sides together provides added comfort and privacy, creating the perfect setup for extended families or two families vacationing together.brbrRoom DetailsbrCasita Eastbr• Primary Bedroom: Queen bedbr• Second Bedroom: Two Twin bedsbrCasita Westbr• Primary Bedroom: Queen bedbr• Second Bedroom: Two Twin bedsbrbrEach casita includes a shared washer and dryer, Wi-Fi, cable TV, air conditioning, and beach gear for guest use. Outdoor showers make rinsing off after beach days a breeze, and the home’s central Siesta Key location provides quick access to bike rentals, kayak tours, and the island’s free trolley.brbrDos Casitas Retreat offers the best of both worlds, two comfortable coastal homes in one convenient Siesta Key location. Whether you’re planning a family vacation or a couples’ getaway, you’ll love the easy access to Siesta Key Beach, local restaurants, and island adventures. brbrBook your stay with Siesta Key Luxury Rental Properties today and start planning your perfect island retreat.brbr-brThis home is managed by Siesta Key Luxury Rental Properties. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. Weight limit of 50lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. See our Siesta Key Luxury Rental Properties Policies for full details. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Super Unit- Dos Casitas Retreat!

Siesta Key, Florida, United States

Bed

Bath

8

Sleeps

$236.02

Harbor Towers Unit 603 by Tropical Sands AccommodationsbrbrHarbor Towers Unit 603 is a beautifully renovated two-bedroom, two-bath condominium located on the sixth floor of the Harbor Towers Yacht and Racquet Club. Offering southern-facing views of the pool and Intracoastal Waterway, this refined residence is ideal for families or two couples seeking a polished, turnkey retreat for an extended stay on Siesta Key.brbrHighlightsbr• 13-night minimum staybr• 2 Bedrooms / 2 Bathroomsbr• Sleeps up to 4 guestsbr• King bed and Queen bedbr• Sixth-floor residence with pool and Intracoastal viewsbr• Recently renovated and professionally decoratedbr• Fully equipped kitchen with new appliancesbr• Smart TVs with cable and fast WiFibr• Elevator accessbr• Assigned parking spacebr• Gated waterfront communitybr• Two heated pools and three Har-Tru tennis courtsbrbrGuests at Unit 603 enjoy Harbor Towers’ upscale, resort style amenities along the Intracoastal Waterway, including two heated swimming pools, three Har-Tru tennis courts, and a 40-slip marina. Additional shared features include a fitness center and sauna, party room, outdoor grilling areas, waterfront seating, and peaceful marina views that define the relaxed luxury of the community.brbrThe condo has been completely renovated and professionally styled with a classy coastal design. The living area is comfortable and inviting, enhanced by modern furnishings, smart TVs, and thoughtful touches throughout. This space flows seamlessly into a fully equipped kitchen with new appliances, making it easy to prepare meals and enjoy time together during your stay. High-speed WiFi, USB charging outlets, and modern conveniences support both relaxation and connectivity.brbrThe primary suite features a king bed and a private ensuite bathroom, offering a calm and comfortable retreat. The guest bedroom includes a queen bed and easy access to the second full bathroom, making it well suited for couples or family members. Both bathrooms have been fully updated as part of the recent renovation.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Guest Bedroom: Queen bedbrbrWith its elevated views, high end renovations, and access to Harbor Towers’ exceptional waterfront amenities, Harbor Towers Unit 603 by Tropical Sands Accommodations offers a refined and effortless Siesta Key escape. Enjoy poolside days, marina sunsets, and a short walk to the nation’s top-ranked beach. Book your extended stay and experience island living at its best.

Harbor Towers 603 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$257.24

Harbor Towers Unit 304 by Tropical Sands AccommodationsbrbrHarbor Towers Unit 304 is a welcoming two-bedroom, two-bath condo located in the gated waterfront Harbor Towers community on Midnight Pass Road in Siesta Key. Recently refreshed and thoughtfully furnished, this condo is ideal for couples, friends, or small families planning a relaxing extended stay near Siesta Key Beach, dining, and island attractions. With a comfortable layout, bright interiors, and a screened lanai overlooking the community grounds, this home offers easy island living in a prime location.brbrHighlightsbr• Two-bedroom, two-bath condobr• King bed, two twin bedsbr• Washer and dryer in unitbr• 13-night minimum stay communitybr• Screened lanai with seatingbr• Recently refreshed interiorbr• Gated waterfront Harbor Towers communitybr• Two heated pools and three Har-Tru tennis courtsbr• Marina, fitness center, and saunabr• Short distance to Siesta Key Beach and the VillagebrbrStep outside onto the screened lanai, where you can enjoy morning coffee or unwind in the evening while overlooking the lush tropical grounds and pool area below. As part of the Harbor Towers community, guests have access to a gated waterfront setting with two heated pools, three Har-Tru tennis courts, a marina, fitness center, and sauna, offering a resort-style experience throughout your stay.brbrThe open concept living and dining area is designed for comfort and relaxation, featuring plush seating, natural light, and a calm coastal palette. This inviting space is perfect for unwinding after a beach day or enjoying quiet evenings indoors. The kitchen is bright and functional, offering granite countertops, ample cabinetry, and essential appliances to make meal preparation easy and convenient during your stay. Whether you are preparing simple breakfasts or home cooked dinners, the space is well suited for extended stays.brbrThe primary bedroom serves as a peaceful retreat with a comfortable king bed, generous storage, and a private ensuite bathroom. The second bedroom is furnished with two twin beds and is conveniently located near the hallway bathroom, making it ideal for additional guests. The hallway bathroom is easily accessible from both the guest bedroom and the main living area, providing added comfort and convenience.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroombr• Second Bedroom: Two twin bedsbr• Second Bathroom: Hallway accessbrbrAdditional conveniences include an in-unit washer and dryer, elevator access within the building, and beautifully maintained community grounds throughout Harbor Towers.brbrWhether you are planning a seasonal escape or a longer Siesta Key stay, Harbor Towers Unit 304 by Tropical Sands Accommodations offers comfort, location, and access to top community amenities. Book your stay today and start enjoying relaxed island living in one of Siesta Key’s most desirable waterfront communities.

Harbor Towers 304 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$240.9

Harbor Towers Unit 410 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers Unit 410, a bright and inviting two-bedroom, two-bathroom condo in one of Siesta Key’s premier gated waterfront communities. Ideal for seasonal guests and extended stays with a 13-night minimum requirement, this beautifully maintained fourth-floor retreat offers peaceful views, resort-style amenities, and a prime location just minutes from world-famous Siesta Key Beach and Siesta Key Village.brbrHighlightsbr• 2 Bedroom / 2 Bathroom condobr• King, 2 Twin bedsbr• 13-night minimum stay communitybr• Short drive to Siesta Key Beachbr• Enclosed lanai with scenic viewsbr• Gated waterfront communitybr• 2 heated community poolsbr• 3 Har-Tru tennis courtsbr• 40-slip marinabr• Fitness center and saunabrbrHarbor Towers is a sought after Siesta Key community known for its exceptional amenities. Guests enjoy access to two heated pools, perfect for morning laps or relaxing afternoons in the Florida sunshine. Tennis players will appreciate the three Har-Tru tennis courts, while boating enthusiasts can take advantage of the 40-slip marina with direct access to the Intracoastal Waterway. The gated community also features a fitness center and sauna, amenities rarely found in many Siesta Key associations, making this property especially appealing for extended stay guests.brbrUnit 410’s enclosed lanai is a standout feature, offering panoramic views and a bright, glass-lined space perfect for morning coffee, reading, or simply enjoying the coastal breeze in comfort. This condo features a light filled open living and dining area designed for comfort and relaxation. The living room offers comfortable leather seating and a television, creating an inviting space to unwind after a beach day. The kitchen is fully equipped with stainless steel appliances, granite countertops, and ample cabinet space. Whether preparing a quick breakfast or a full dinner, you will have everything needed for a seamless extended stay experience. The adjacent dining area provides comfortable seating for shared meals and gatherings.brbrThe primary bedroom features a king bed, large windows with natural light, and direct access to the ensuite bathroom. The ensuite includes a spacious vanity and a walk-in shower, offering privacy and convenience. The second bedroom is furnished with two twin beds, making it ideal for visiting family or guests. A hallway bathroom with a shower and tub combination is easily accessible from both the guest bedroom and main living area. Each bedroom is thoughtfully designed to provide a restful and peaceful environment, perfect for longer stays on Siesta Key.brbrRoom Detailsbr• Primary Bedroom: King bed and ensuite bathroom with walk-in showerbr• Second Bedroom: Two twin bedsbr• Hallway Bathroom: Shower and tub combinationbrbrHarbor Towers Unit 410 includes beautifully maintained grounds, community grilling areas, elevator access, and assigned parking. The 13-night minimum stay requirement helps maintain a peaceful atmosphere, ideal for snowbirds, seasonal visitors, and guests seeking a longer Siesta Key retreat.brbrIf you are searching for a Siesta Key vacation rental with resort style amenities, scenic views, and the comfort of an extended stay community, Harbor Towers Unit 410 by Tropical Sands Accommodations is the perfect choice. Reserve your preferred dates today and experience the relaxed coastal lifestyle that makes Siesta Key a favorite year after year.

Harbor Towers 410 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$677.53

Coconut House | Siesta Key Retreat with Shared Heated Poolbrbr Why You'll Love This HomebrStep into a bright, spacious haven perfect for your Siesta Key getaway. Coconut House features three inviting bedrooms, a fully equipped kitchen for group meals, and access to a screened-in heated pool shared with Palm Shade Cottage. Just 0.1 miles from the white sands of Siesta Key Beach, this home blends indoor comfort with outdoor fun.brbr ‍ ‍ Perfect ForbrFamilies or small groups seeking a convenient home base with separate living space, shared outdoor amenities, and easy beach access.brbr ️ Imagine ThisbrWake up to the warm Florida sun and prepare breakfast in your fully equipped kitchen. Take a short 0.1-mile stroll to the world-famous Siesta Key Beach for morning swims and sandcastle building.brbrReturn home to fire up the grill for a family BBQ, then enjoy a refreshing dip in the screened-in heated pool. Share stories under the stars as the day winds down in this serene, shared outdoor space.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bathroom, Ground Floor, TVbr• Bedroom 2: King Bed, Shared Hall Bath, Ground Floor, TVbr• Bedroom 3: Two Twin Beds, Shared Hall Bath, Ground Floor, TVbrbr Explore the Areabr• 0.1 miles to Siesta Key Beach – White sand, turquoise waters, public beach accessbr• 0.3 miles to Siesta Key Village – Boutique shops, island eateries, and nightlifebr• 0.2 miles to Local Cafés and Bakeries – Fresh coffee, pastries, ocean viewsbr• 0.4 miles to Siesta Public Beach Park – Kayak rentals, picnic areas, family-friendly activitiesbr• Coastal energy with quiet residential streets for leisurely strollsbrbr⌛ Don't Wait - This home is part of our CottageClean™ Program: a 6-hour deep clean followed by a 35-point inspection for total peace of mind. Homes this close to the beach with a heated pool book fast!brbr Need to Know: Coconut House is part of a two-unit duplex and shares outdoor space and amenities with Palm Shade Cottage. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights.

Coconut House | Shared Heated Pool, Amazing Location Near Main Beach Access!

Siesta Key, Florida, United States

3

Bed