Vacation Condo Rentals By Owner In Siesta Key, FL

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.brbrThis Siesta Key Dream’s vacation rental features a bright, welcoming 1 bedroom, 1 bath space. You’ll experience an open floor plan connecting a welcoming living room and kitchen with a stove, fridge, & microwave. In a separate room, you’ll see your comfortable king bed and a private bathroom. The living room has a queen size sofa-bed allowing for a capacity of four guests. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, an HD Television equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat.brbrOutside this unit, you’ll see a private, screened-in porch with lounge chairs and a ceiling fan that is perfect to relax in the shade, while enjoying the Florida Keys weather and a view of the surrounding neighborhood. brbrSiesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. brbrIf you’re looking to soak up the sun and clear waters, the beach access point is a mere 100 steps away from this property. Easily slip on your sandals and take a 2-minute stroll to experience the brilliant 99% white quartz sand. brbrIn addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and entertainment options from gourmet donuts, coffee, and seafood to award-winning steakhouses. brbrWe recognize that parking can be difficult at times to locate, which is why this rental comes with ONE private, reserved space at no additional cost to you. Alternatively, we offer an exclusive upgrade which includes a golf cart rental for easy travel and access to all the top tourist spots around town. The Siesta Key Breeze Trolley also operates on the main roads outside your rental, which is free for all riders and operates 8 AM - 10 PM, seven days a week!brbrSiesta Key Dreams wishes to provide you with `Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable.brbrIncluded within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! brbrShortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes.brbrWhen available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. brbrGuests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. Before you check-in, and just after booking, we require guest verification. You will receive information after booking and the process only takes a couple minutes. This allows us to provide a safe location for our guests, neighbors, and employees.brbrLooking for a larger space Siesta Key Dreams rents the entire complex, combining both 1-bedroom condos and the 3-bedroom home.

100 Steps to beach access - 5 minute walk to the Village - Private Porch

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$387.1

Please, Saturday - Saturday rentals only. brSATURDAY - SATURDAY RENTALS ONLYbrWelcome to Siesta Key! Come, relax and take in the top floor views of the #1 rated beach in the United States. The condo was professionally designed to accentuate your “beach time”. Enjoy the updated decor, furniture, king bed, and fully equipped kitchen complete with Keurig single serve/carafe combo coffee maker. All linens are provided including sheets, towels, beach towels, beach chairs and umbrella. There are two cable tv's, and WiFi for internet access. The patio offers top of the line Ratan lounge chairs and a love seat so you can relax and enjoy the 180 degree view of the beach.brbrEnjoy the wonderful full-size pool right outside your back door. Elevator Access to our top floor condo with the fabulous view. Coin operated laundry located on every floor of each building, Reserved parking spot; outdoor grills and shuffleboard fun are waiting. Walk through the Siesta Key Village where shopping and dining options are everywhere and only minutes from your home. If you are in the mood to explore, Sarasota has many fine art galleries, upscale shopping, dining, golf, theatre, sunset dinner cruises and sailing on the Gulf.brSaturday-Saturday rentals only please. 7-day minimum.

Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$292.96

This coastal, two bedroom, two bath condo offers everything you need for a relaxing stay. It is located on beautiful Siesta Key, with the number one voted beach in the USA. There is a fully equipped kitchen where you can prepare family meals. The comfortable living room is furnished with a large screen tv and free WiFi. Enjoy sitting on the lanai overlooking the resort-style swimming pool. Just a short walk to the beach, it’s perfect for couples, families, or friends looking to unwind in the sun. brbrThe spacebrOur condo is located on the second floor and overlooks the heated pool. You’ll have full access to the entire space during your stay. Please note that two interior closets are locked and reserved for the owners. The beach supplies closet is conveniently located on the lanai, with chairs, umbrella, and beach wagon. Also includes fishing gear for fishing in the Intercoastal waters off the pier.brbrGuest accessbrYou have access to the entire condo except for two small closets. Full access to clubhouse and swimming pool.brbrOther things to notebrFull streaming 4k TV's are available in 3 rooms but logins are not provided. You are welcome to login to your own accounts. A small dedicated workstation for those who need to conduct business.brbrWe are a 13 minute walk to the closest public beach access, which is #12, brCrescent Beach and a 5 minute drive to the Main Siesta Beach access with large parking lot and restrooms.brThe Breeze trolley picks up at our condo and takes you everywhere on Siesta Key, including restaurants, all beach access points, shopping, etc.brbrWe do require you to be 25 yrs. of age to reserve our condo.

Sunny Beach Retreat on Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$353.59

Walk out your door to enjoy all the Siesta Key white sands have to offer. This 1-bedroom, 1.5-bath unit is ready for your immediate enjoyment. Enjoy vaulted beamed ceilings throughout, and a fully equipped kitchen conveniently, open to the dining nook and living room areas. The living room features a new pull-out queen sofa bed and closed in lanai with a dining area. The master bedroom includes a king-size bed and plenty of closet space. Casa Mar's community amenities include 2 sparkling swimming pools, a tennis/pickleball court, beach volleyball, 4 picnic areas with gas BBQs, and 4 shuffleboard courts. Don't miss this opportunity to enjoy all that Siesta Key has to offer from the comfort of this beautiful beach condo!brbrBedroom- KingbrLiving room- Queen Sleeper Sofa and Twin Trundle BedbrbrAdded 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: 23 br*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

Beautiful Ground Floor 1bed/1.5 Bath Condo with Pool and Beach Access!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$287.54

Wow, it doesn't get any better than this. Stay the month or two on Siesta Key in Florida. Come home to this true beach condo with white Florida decor, ground floor location RIGHT across from the famous newly remodeled Siesta Key Pavilion! The beach is a short walk away. Siesta Key Beach, with its soft quartz sand and turquoise, was voted #1 Beach in the USA and #5 in the WORLD by TripAdvisor 2017. You can't get much closer than this prime location condo - 2 King Bedrooms, both with en-suite baths. Tiled floors, ground floor with dedicated parking space and guest parking. Walk to Siesta Key Village.

Ground-Floor Monthly Condo Facing Siesta Key Beach!

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$412.66

Welcome to one of the most beautifully renovated and professionally decorated condominiums on Siesta Key. This stunning two-bedroom, two-bath residence offers more than 1,200 square feet of upscale coastal living and delivers the perfect blend of luxury, comfort, and relaxation.brbrThoughtfully designed with elegant finishes and high-end furnishings throughout, this immaculate condo features a bright, open layout with sophisticated coastal décor and a true resort-style atmosphere. From the moment you walk in, you’ll feel right at home in paradise.brbrThe spacious living area opens to a private screened lanai, the perfect place to enjoy Gulf breezes, morning coffee, or spectacular sunset views. The fully equipped kitchen features modern appliances, quality cabinetry, and everything needed for dining and entertaining with ease.brbrThe primary suite offers a luxurious king bed, serene coastal styling, and a beautifully updated en-suite bathroom. The guest bedroom features two queen beds, ideal for children, friends, or additional guests, along with easy access to the second full bathroom.brbrAdditional amenities include high-speed Wi-Fi, flat-screen televisions, and premium furnishings throughout the residence.brbrLocated just steps from the world-famous white quartz sands of Siesta Key Beach, this exceptional condo places you in the heart of paradise. Guests enjoy resort-style amenities including a heated Gulf-front pool, fitness center, BBQ grilling area, and beautifully maintained tropical grounds. Nearby restaurants, boutique shopping, and the free village trolley make exploring Siesta Key effortless and enjoyable.brbrWhether you’re planning a relaxing beachfront getaway or a memorable family vacation, this exceptional residence offers the very best of luxury coastal living.brbrReserve your dates early—this is one of our most sought-after vacation homes.

Stunning 2BR 2 BA Gulf Views Luxury

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$378.0

Newly renovated and Decorated Penthouse with ocean views. This 5th floor unit is located Two blocks from the famous MTV “Siesta Key” Crescent Beach and 4 blocks from the #1 beach in the country Siesta Key Beach. If walking is not your thing you can take the free trolley anywhere on the Island. The master has a new King size bed and its own bath that was just redone with beautiful tile and granite work. The second Bedroom has a new Queen and single bed also with its own freshly redone bathroom. There is also a roll out bed if needed. The open kitchen with breakfast bar has granite tops and new stainless steel appliances all that one would need. The New Washer and Dryer are located in the kitchen area. Living room and Dining room combination were just refurnished and has a very comfortable feel to it. You can sit outside on the Lanai for your morning coffee or evening cocktails. You can also gain access to the storage closet that has the items needed for the beach. There are new smart Televisions in both bedrooms and a new 65 inch smart TV in the living room. Wi-Fi, covered parking, elevator and luggage cart all to make for an easier stay. Bay Oaks is located on the bay across the street from the beach. It has its own fishing pier, or a place to sit out and just watch the boats go by. It has BBQ area, picnic tables, Tennis courts, heated pool, club house with pool table and park like grounds. Just down the road you will find boat, jet ski, and bicycle rentals, Excellent restaurants, stores and entertainment in Siesta key Village.

Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$325.87

Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the island of Siesta Key off Sarasota, Florida, this vacation home has the best of both worlds - the beach in front and boat docks with access to the Intracoastal Waterway in back. Fisherman's Cove is practically surrounded by water!brbrThis unit is on the ground floor and you can walk right out the lanai onto the sand!! Flooring has been upgraded with modern plank tile throughout. The renovated kitchen has granite counter tops and modern appliances including refrigerator, glass top range/oven, dishwasher and microwave. The kitchen is fully equipped including a range of small appliances and Kuerig coffeemaker. The dining area has seating for six (including two bar stools) and is right off the kitchen. The living room has a new extra thick mattress in the queen sleeper, large flat panel HDTV and an amazing view out to the lanai and the Gulf. The air-conditioned lanai has sliders looking out to the Gulf of Mexico and the beach. This unit also has glass sliders between the living room and Lanai giving the option of closing it off so the inside is air-conditioned but sliders can be opened on the Lanai. It is furnished with chairs and table to let you get comfortable as close to the water as possible.brbrSleep at night with the ocean surf right outside your window! The master bedroom has a bay window overlooking the Gulf and beach below. It has a king-size bed, large HDTV, walk-in closet, and en suite bathroom with a tiled tub/shower combo.brbrThis unit has its own dedicated high-speed broadband WiFi. Coin-operated laundry washer/dryers are only steps down the walkway. Boat docks are available for guest use at no extra charge!! Bring your boat or rent one after you get here. Keep it right at the condo all week long. (Note; trailers cannot be stored on site)brbrFisherman's Cove is located less than 25 minutes from Sarasota airport, 90 minutes from Tampa, and two and a half hours from Orlando. Tons of great restaurants and golf courses are nearby.brbrSleeping Arrangements - Comfortable sleeping options make this unit ideal brPrimary Bedroom: King bed, private en-suite bath brLiving Room; Sleeper Sofa

Wake Up to the Gulf – Beachfront Living

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$477.24

Our spacious 2/2 unit is located on the beachside of Siesta Key. No need to cross the road to get to the beach - we have a private, guest-only gate entry right next to our building that leads directly to the beautiful Crescent Private Beach, just about 120 yards away. There are lounges and chairs available right off the path for you to enjoy. We also offer a temperature-controlled community pool for your enjoyment. We are located approximately 1 mile from Siesta Key Village, where you can enjoy dining and shopping.br*As of May 4th we will offer streaming only on our TV's. Please bring your sign-in's.

Siesta Key, Private Crescent Beach 2/2 Getaway

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$371.78

Located just north of the Stickney Point bridge, this beautiful 2 bedroom, 2 bath condo just steps from Siesta Key Beach! Located on ground level, this unit also puts you steps away from the pool! This unit is comes with 1 king bed and 1 queen bed, plus a full kitchen with refrigerator & dishwasher. Television with basic cable, wireless internet, and a private washer and dryer.

Siesta Key - Midnight Cove #211

Siesta Key, Florida, United States

Bed

Bath

4

Sleeps

$427.14

Brand new pool !brbrOur place on the #1 Siesta Key beach is near Siesta Key village, quiet turtle beach, downtown Sarasota, Lido Key, St Armand s circle and LongBoat Key. You’ll love our place because of the location, and the ambiance. The best feature - few steps to private Crescent beach (no hike across busy streets to get to the beautiful crystal sands!) brThe building is on a quiet street with no through traffic making it a pleasure to roam safely. brbrOur unit was not at all damaged by the 2 major hurricanes in 2024. Renovations to other units are wrapping up. brbrHappy to answer any questions any time!!

Stylish Retreat on Private Crescent Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

Select Dates for Price

Escape to this lovely condo in picturesque Siesta Key. This marvelous property features 2 cozy bedrooms, one with a queen bed and the other with 2 twin beds. With 2 bathrooms including a bathtub and hair dryer, guests will feel right at home. Our place is equipped for both long or short stays to make your holiday one to remember.

Our House at The Beach C222, 2-bedroom condo just steps from Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$420.75

Spend your island paradise vacation in this 2 bedroom, 2.5 bath condo on Siesta Key! This beautiful home offers an open floorplan with room for up to 5 guests. Enjoy beautiful views of the gulf from the open-air balcony, or relax on the beach and enjoy the peaceful tropic breeze. This complex also offers a small workout-room for your use. With 13 public beach access points, wonderful shops and restaurants, Siesta Key promises great experiences for everyone who visits. Take advantage of the tranquil waters, soft sand, and warm sun as you explore all the island has to offer and unwind at the end of a fantastic day in this beautiful home.brbrBedroom 1 - King,brBedroom 2 - Full and Twin,brbrAdded 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!brbrPlease Note: Golf-Carts are NOT allowed on property grounds.brbr*Minimum Age to Book: 27 br*Security Authorization Hold taken upon check-in. Amount: $1,000

Stunning 2 Bedroom Condo with Beach & Pool Access on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$318.11

Miles and miles of white sand from the gentle waves of the Gulf of MexicobrbrOur 1350 sq ft 2 bedroom 2 bathroom unit has an updated kitchen with plenty of space to cook while being open to entertain guests as well. Expect luxurious, queen-size beds in a master bedroom and in a guest bedroom, spacious sitting area, separate dining spaces, granite countertops bathrooms with soaking tub, and free Wi-Fi. Two big screen plasma TVs in the living room and bedroom. With direct access to the Crescent beach, guests can indulge in the best laid-back living in the country. Relax on your private balcony or sit on the beach voted #1 in the USA for 2024! This beautifully landscaped property has an excellent swimming pool, grilling stations, launch chairs on the beach, as well as one car parking, fitness center, and tennis courts.brbrFebruary and March rent is charge only for a full month.

Heaven of Siesta Key, one step to #1 beach in Sarasota

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$157.49

2 week rental minimum from April through December. January, February March, are monthly rentals please select the first day and last day of the month when booking. There is currently January 2026 still available.brbrSiesta Key Beach Vacation Rental: Location- location-location-BEACH, VILLAGE, HEATED POOL.brbr Walk across the street to the beach, walk or take the free trolley to the village, or decide to sit in a heated saltwater swimming pool!brbrSTAY AT THE CENTER OF IT ALL! Master Planned condominium to ensure your comfort and needs. brbr This condo has everything you need - just pack your suitcase. brbrIdeal location, This beach condo is located across the street from Siesta key Beach with direct access to Beach & just a few blocks to The charming Siesta Key Village. Stroll or hop a trolley ride anytime through the village where you'll find loads of restaurants, boutiques and more. brbrDog friendly one small dog under 25 pounds. brbrWhat's so special about this Beautiful beach The QUARTZ WHITE SAND feels like - baby powder. Your feet have never touched sand like this. No wonder why Siesta Key Beach gets voted the BEST WALKING BEACH in the USA by, USA Today International Edition; and the BEST OF THE BEST SAND by, Condé Nast Traveler Magazine. This beach is like a dream & hard to compare to any other. brbrPicture Miles of the finest white sand with NO pesky rocks to climb over, framed with mesmerizing crystal blue waters. Be free and relax on your beach chair and be amazed. You'll find it very hard to leave this place. You'll want to come back again and again.brbr Enter the condominium grounds through a tropical setting to your own covered private parking space designated just for you. brbrEnjoy the: Heated Salt water Pool, Sauna, Gas Barbecue Grills or just wander the beautiful seven acre landscaped tropical grounds. We have our own private Marina on the premises where you could see pretty fish and maybe spot manatees if they happen to be passing by. brbrStep into this elegant & spacious non-smoking 2nd floor condo that is well stocked with everything you'll possibly need. Beautifully decorated with your comfort in mind. brbrIn addition to it's Beachy garniture, and comfortable flooring that looks like driftwood. This condominium is immaculate and includes the modern comforts of home. Fully equipped just like home. brbrFeaturing a Completely stocked galley kitchen with granite counter tops and a shimmery glass tile backsplash. The latest and greatest hammered copper farm style sink gives the finishing touches. The high end maple cabinets are brand new. A great place to park your iPhone or iPad you will find a USB outlet, super convenient! Everything in the kitchen is like home so feel free to make a delicious meal.brbrInviting dining area - features: leather seating and a wall of Mirror to brighten up the space. brbrExquisite Living room that includes: pullout-Queen Sofa, with a plush shag carpet. flat screen Smart-TV with basic cable, Wi-Fi connection. Two cozy swivel chairs with Additional cocktail tables. brbrFreshen up in a Brand-new bathroom with easy walk-in tiled shower that has a handrail for your safety. A blow dryer stocked under the sink along with a first aide kit. brbrThe linen closet will provide you with fresh linens, towels, sheets, pillows, pillow cases, extra blankets, A safe for your precious valuables, A fire extinguisher, and iron and ironing board, complete Beach gear: caddy, Beach chairs, Beach umbrellas, Beach towels and more. brbrA gigantic bedroom tastefully decorated including: USB outlets at the night table. Alarm clock,. Two huge closets, plus plenty of room to store your clothes in the dressers and night tables. A spacious desk & chair is also provided for your convenience. brbrScreened in lanai, a great place to relax and have a cup of coffee with a Garden-view with Park like setting. This space is decorated with festive string lights for the evening, you just have to plug them in and enjoy the vacation excitement. Very comfortable seating and the decorations will keep you mesmerized.brbrNo keys! An easy PUNCH - PAD entry has been installed to make it even easier for your access. brbrLaundry Facility conveniently located directly below unit on the ground floor level. brbrCondominium is on the second floor with steps. brbrAll you need is to pack your suitcase you'll find everything you need to have an enjoyable comfortable stay at The world famous Siesta Key Island.brbrPrivately managed to assure everything goes smoothly. We care about our guests comfort and satisfaction. Attentive Manager will be there for you 24/7 if you have any questions. We're easy to reach and ready to serve you. brbrBOOK NOW WITH CONFIDENCE you're in good caring hands!brbr2 week or more rental minimum.brbrOnly four person occupancy – minimum renting age must be over 25 years old-must acknowledge condominium rules and regulations to keep our neighbors happy.brbrOne small dog allowed with permission only please inquire first before booking. Pet owner must sign a waiver policy before check-in date. Dog must weigh 25 pounds or under. Dog fee is $125 per stay. Please don’t show up with your dog without permission you will be asked to leave without a refund. No cats allowed.brbrStrict smoking rules: absolutely No smoking or Vaping in the building. A $300 fee will be charged if Cleaning Person smell cigarettes.brbrWe appreciate and expect responsible guests to ensure the well-being and safety of others.brbrSiesta Key Public Beach amenities include: br. Public restrooms, snack bar & gift shop br. Showers and handicap ramps br. Picnic areas with & without roofs br. Picnic shelters & tables (8 - family size shelters) br. Gazebos (holds up to 60 people) br. Large shelter (holds up to 120 people) br. Free lighted public tennis courts br. Volleyball courts (on the beach) br. 20 station fitness trail br. Playground equipment br. Lifeguards on duty year round br. Handicap beach chairs/wheel chairs available brbrTransportation: condominium located within 10.9 miles from Sarasota airport. Tampa airport is approximately an hour and a half ride. Punta Gorda is also a good choice, a small airport 52 miles away from this condo. brbrFree trolley rides on Siesta Key that run up and down the main road of the island. The trolley runs till midnight on weekends and during the weekend till 10 o'clock. The trolley also runs on all holidays. brbrSCAT buses run throughout the area.brbrYou can RENT BABY GEAR if needed here on Siesta Key. Several baby gear businesses will deliver & pick up all your baby gear with A large assortment of items to choose from. They also have a babysitting services. brbrDisney world is a little over a two hour drive.brbrSiesta Key and surrounding area has lots of things to see and do, A share book is located in the condo to browse through terrific suggestions on activities, restaurants, sightseeing and more. The possibilities are endless.brbrbrbrbrbrbrbrbrbr

Siesta Key Beach IDEAL LOCATION BEACH, VILLAGE, HEATED POOL

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$340.45

Enjoy your visit to TripAdvisor's #1 beach in the USA. This marvelous condo in Siesta Key offers 2 en-suite bedrooms, one with a king bed and the other with 2 full beds. The 2 bathrooms are equipped with a bathtub, shower, and hair dryer for your convenience. Relax in front of the fireplace and watch TV. Enjoy coffee on the lanaii overlooking the pool. With a free trolley stop right out front, you'll have access to downtown Sarasota, all the Siesta Key Beaches and shopping without needing a car. Our complex includes a heated pool, pickleball/tennis court, and a fishing dock on the intercoastal. The nearest beach access is a short 0.4 mile walk. Walk to dinner at Captain Curt's or Spearfish Grill then follow with live music or Karaoke at the SnikiTiki. This delightful retreat is the perfect spot for guests looking to unwind, and enjoy a fantastic getaway. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.

Perfectly located on Siesta Key. Our updated paradise is now yours to enjoy too!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$309.14

The Anchorage Resort on Siesta Key - includes resort amenity access!brbrOur 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.brbrAnchorage Resort Condo br* 2 bedrooms / 2 bathroomsbr* Seventh Floor Condo with balcony overlooks South-Eastern Siesta Keybr* Fully equipped Kitchen with seating for 6 at the dining tablebr* Beach Supplies include- 4 Chairs, Umbrella, Raft/Float Items, Beach Towelsbr* Community Pool- Largest pool on the Key!br* Gated Communitybr* Siesta Key Trolley- free pickup in front of the resort entrancebr* Private Beach access to Crescent Beach across the streetbr* 25-year minimum age to rent restrictionbrbrBEDROOMS (Seventh Floor Condo)brBedroom 1: One King Bedroom (Ensuite Bathroom) / Balcony Access / 50 TVbrBedroom 2: Two Double Bedroom / Balcony Access / 19 TVbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courts* Shuffleboardbr* Community BBQ areabr* Individual Picnic areas along the Canal/Intracoastal Waterwaybr* Exercise Roombr* Bike & Kayak Racks (subject to availability)br* Boat Dock/Seawallbr* Coin-Operated Washer/Dryer on Each FloorbrbrPool Information:br- Community Poolbr- HeatedbrbrResort Parking Rules:brThe resort allows a maximum of 2 cars.brVehicles must be registered with the front office during office hoursbrbrHOA Rules:brLead guest must be age 25 or older. ID is checked upon registration at the resort.brNo petsbrJanuary 1- April 16 Rentals are 7-nights beginning and ending on Saturday onlybrbr brDistances from Resort to Shopping & Attractions:br* Daiquiri Deck South Siesta Key- 5-minute walk across the streetbr* Crescent Beach Private Beach Access- 7-minute walk across the streetbr* Toasted Mango Cafe - 9-minute walkbr* Siesta Key Watersports - .6 milebr* Siesta Key Village- 2.7 (trolley stop)br* Publix at Sarasota Pavilion- 1.4 milesbr* Marie Selby Botanical Gardens - 6 milesbr* Sarasota Bradenton Airport (SRQ) - 11 milesbr brWhy Choose this Rental br- Professionally managed to serve all your needsbr- Management company has over 26 years of experience hosting well over 200,000 familiesbr- Go straight to your rental with online email check-inbr- 24/7 on-call maintenancebr- Free On-Site Parkingbr- Smoke-free and pet-free for your comfortbr- Towels and linens are providedbr- Complimentary WiFibr brOur Starter Welcome packet supplies:br- 2 rolls toilet paper per bathroombr- 1 hotel-size bar soap per bathroombr- 1 hotel-size shampoo/conditioner per full bathroombr- 1 roll paper towelbr- 2 packet dishwasher detergentbr- Size 13-gallon Trash bagsbrAny supplies beyond this are up to the guest to replenish, we do not restock these items. brNo salt/pepper or cleaning supplies are stocked due to safety issues. brThis is an industry-standard practice.br brFOR GUESTS WHO BOOK 30 NIGHTS OR LONGER STAYS: (this does not apply if you are staying less than 30 nights)brWe will collect a $1,500 deposit.brBalance is due 60 days prior to arrivalbrIf canceled 90 days or more before arrival, we keep with us $250.00. $1,250.00 will be refunded.brIf canceled between 61 and 89 days prior to arrival, we keep with us the $1,500.00 deposit.brNo cancellation or modification 60 days or less prior to arrival.

Anchorage Resort 7th Floor 2-Bedroom Condo w Private Balcony Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$335.81

Direct Gulf of America access · Jamaica Royale Condominiums · Siesta Key, Florida · Sleeps up to 6 · 3 heated pools · Free covered parkingbr brCompletely renovated in spring 2025, this beautifully updated condo sits on a private lane leading directly to the world-famous white sand beaches of Siesta Key — no roads to cross, no long walks. Just step outside and stroll to the Gulf. The kitchen features brand-new quartz countertops, every room has been refreshed, and the result is a bright, comfortable retreat steps from one of the top 10 beaches in the world.brbrTraveling with another family or group A second property is available just 5 doors away (VRBO #1879830). Search that number on VRBO to view the listing and keep your group close together. br brbrPRIMARY BEDROOM AND BATH: King pillow-top bed, 43 HD flat-screen TV, blackout curtains, and a desk perfect for a laptop or vanity. En suite bathroom with a walk-in shower.brbrGUEST BEDROOM AND BATH: Two queen pillow-top beds, 43 HD flat-screen TV, and blackout curtains. Full bathroom with tub/shower combination directly across the hall.brbrLIVING ROOM: 55 HD flat-screen TV with FIOS hi-definition service. Amazon Prime and Netflix available on all three TVs throughout the unit.brbrKITCHEN AND DINING: Fully remodeled with quartz countertops and all the essentials — coffee maker, toaster, microwave, and blender. Dining table seats 4, with additional outdoor seating for 6 on the private patio.brbrPRIVATE PATIO: Outdoor dining set with a 9' shade umbrella. Tucked away from the pool area for a quiet, peaceful setting.brbrLAUNDRY: In-unit washer/dryer. On-site laundry facility also available.br brPROPERTY AMENITIES:br3 heated freshwater pools · Private beach exclusively for Jamaica Royale guests · Beach chairs & towels provided · Beach buggy, coolers & beach toys · 2 BBQ areas with beach-side pavilions · Shuffleboard courts · Free assigned covered carport parking · Dedicated high-speed FIOS Wi-Fi · Digital keypad entry (unique code per stay) · Free Siesta Key Trolley stop at the entrance br brLOCATION:brJamaica Royale Condominiums is set directly on the Gulf of America along Siesta Key Beach — consistently ranked one of the top 10 beaches in the world. The property sits on a quiet private lane with no through traffic, making it especially safe and easy for families with children. The “free trolley” stop is right outside the entrance lets you explore the Key without a car. Tennis courts and a large playground are less than half a mile away at Siesta Key Public Beach, and the Stickney Point Road intersection is just 1.1 miles away.br brGOOD TO KNOW:brCheck-in is targeted for 3 PM. On request, an ozone generator can be run before your arrival to sanitize the unit — this extends prep time by about 2 hours. A brand-new digital entry code is created for each guest stay, so there are no keys to worry about. brbrThe owner is available throughout your stay and typically responds within hours.

GULF SIDE - Peaceful Private Condo, 2BR/2BA, Siesta Key Jamaica Royale #100

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$270.0

Sunset Royale – 314 by Tropical Sands Accommodations brbrWelcome to Sunset Royale – 314, a bright and inviting two-bedroom, two-bathroom Siesta Key vacation rental located directly across the street from the white sands of Siesta Key Beach. Situated on the third floor, this beachy condo features Gulf views, an open and airy floor plan, and a private enclosed lanai that creates the perfect setting for morning coffee and unforgettable sunset views. With beach amenities included, covered parking, and an easy walk to Siesta Key Village, this condo delivers relaxed island charm and everyday convenience. brbrHighlights br• Across the street from Siesta Key Beach br• 2-bedroom, 2-bathroom br• 2 Queen beds br• Gulf views br• Shared elevator br• Shared laundry facilities br• Private enclosed lanai br• Beach chairs and beach towels provided br• BBQ grills and picnic tables br• 1 Covered parking br• Walk to Siesta Key Village brbrSunset Royale – 314 shines with its private enclosed sunroom, offering Gulf views and a comfortable space to relax throughout the day. Whether enjoying a quiet breakfast or watching the sun dip below the horizon, this space quickly becomes a favorite. Guests also enjoy access to shared BBQ grills and picnic tables, ideal for casual outdoor meals. A private beach locker stocked with beach chairs, umbrellas, and beach toys makes trips to the beach effortless, just steps from your door. brbrThe open concept living and dining area is bright, beachy, and thoughtfully furnished to create a welcoming environment for relaxation. Comfortable seating and a TV make the living room perfect for unwinding after a day in the sun. The fully equipped kitchen features white Corian countertops, ample cabinetry, and essential appliances, making it easy to prepare everything from quick breakfasts to relaxed dinners. Dining options include a dedicated indoor dining table as well as additional seating in the enclosed lanai, allowing you to enjoy meals with scenic Gulf views. brbrThe primary bedroom offers a comfortable queen bed, a large window with beautiful Gulf views, a private ensuite bathroom with tub and shower, and a walk-in closet. The guest bedroom also features a queen bed and a walk-in closet, with a full hallway bathroom featuring a tub and shower conveniently located nearby. Each bedroom is designed to provide a peaceful and restful retreat. brbrRoom Details br-Primary Bedroom: Queen bed, ensuite bathroom, walk-in closet br-Guest Bedroom: Queen bed, hallway bathroom, walk-in closet brbrSunset Royale – 314 is ideally located for guests looking to experience the best of Siesta Key. Siesta Key Village is within walking distance and offers a variety of dining options, beachside cafes, ice cream shops, and unique island boutiques. Nearby activities include boating, fishing charters, jet skiing, parasailing, and golfing, making this an excellent choice for both relaxation and adventure. Private secured WiFi, provided linens and towels, and covered parking add extra comfort to your stay. brbrWith stunning Gulf views, a spacious sunroom, and an unbeatable location across from the beach, Sunset Royale – 314 by Tropical Sands Accommodations is a wonderful choice for a relaxed and affordable beachfront stay on Siesta Key. Book your getaway today and experience why the best place to be is at the beach! br br- br1 WEEK MINIMUM STAY REQUIRED brThis property does not allow pets of any kind. brbr1 car maximum is 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. brbrPlease see our Tropical Sands Accommodations Rental Policies for full details. brbrThis home is managed by Tropical Sands Accommodations. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Elegant condo with beach views - Sunset Royale 314

Siesta Key, Florida, United States

Bed