Vacation Rentals By Owner In Siesta Key, FL

Get ready to relax in this 2-bedroom condo in Siesta Key. This welcoming property offers all the essentials for a comfortable stay, including heating, WiFi, and a washing machine. With a brilliant location and cozy atmosphere, guests will feel right at home during their vacation. It's easy to see why you'll be able to unwind at our place.

Charming 2-bedroom condo walking distance to Siesta Key’s beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$391.28

House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds and a sofa bed in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!brIsland

Villa

Island House Beach Resort Villa 39

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$293.58

Gulf and Bay Club Unit B408 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit B408, a comfortable two-bedroom, two-bath condominium located within the highly sought after Gulf and Bay Club community on Siesta Key. This well appointed retreat is ideal for extended stays, offering a relaxed coastal setting just a short walk from the beach and access to an impressive collection of resort style amenities.brbrSituated along Midnight Pass Road, this condo places you minutes from the world famous sands of Crescent Beach and close to Siesta Key’s dining, shopping, and outdoor recreation. Whether you are planning a seasonal escape or a long-term coastal stay, Gulf and Bay Club B408 provides comfort, convenience, and a prime island location.brbrHighlightsbr• 5-minute walk to the beachbr• 2 Bedrooms / 2 Bathroomsbr• King bed, Queen bed, Twin bedbr• Washer and dryer in unitbr• One assigned parking spacebr• Gated communitybr• Shared pool and hot tubbr• Shared fitness centerbr• Tennis and pickleball courtsbrbrGuests of Gulf and Bay Club enjoy access to an outstanding lineup of shared community amenities. Spend your days lounging by the expansive shared pool, unwinding in the hot tub, or staying active at the on site fitness center. Tennis and pickleball courts, shuffleboard, cornhole, and a clubhouse provide plenty of opportunities for recreation and socializing throughout your stay. These well maintained amenities make Gulf and Bay Club a favorite choice for longer Siesta Key vacations.brbrThe interior of Unit B408 is thoughtfully designed for comfort and everyday living. The living area offers cozy seating and a welcoming space to relax after a day at the beach. The fully equipped kitchen includes a refrigerator, stove, oven, dishwasher, microwave, toaster, and a regular drip coffeemaker, making it easy to prepare meals during your stay. A dining area nearby provides a comfortable spot for enjoying home cooked meals or casual breakfasts before heading out for the day.brbrThe primary bedroom features a king bed and a private ensuite bathroom, creating a peaceful retreat for restful nights. The second bedroom offers a queen bed and a twin bed, making it ideal for guests or visiting family. A shared hallway bathroom serves the second bedroom and common areas, providing convenience and privacy for everyone in the condo.brbrRoom Detailsbr• Primary Bedroom: King bed with ensuite bathroombr• Second Bedroom: Queen bed and Twin bedbr• Hall Bathroom: Full bathroom with hallway accessbrbrAdditional conveniences include in unit washer and dryer access and one assigned parking space. Please note this property is not pet friendly.brbrExperience relaxed island living at Gulf and Bay Club Unit B408 by Tropical Sands Accommodations. With resort style amenities, a short walk to the beach, and a location perfect for extended stays on Siesta Key, this inviting condo is an excellent choice for your next long term getaway. Reserve your dates today and settle into the coastal lifestyle you have been dreaming of.

Gulf and Bay Club - B408

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1192.97

Kaia's Sara Sea 4BRbrNewly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Listing includes two 2BR units in nearby buildings (total 4BR). Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Separate Units – 2 units deliver space and privacybr∙ Front Porch – southwesterly porch on the palms (shared)br∙ Beaches – 1-min walk to award winning beaches, white sand, calm waterbr∙ Relaxing – private balcony and patio with dining and loungingbr∙ Pool – beautiful heated pool with tropical plants just 1-minute walkbr∙ Reef Snorkeling – 70-yard walk to Point of Rocks, free snorkel gear providedbr∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets –1-minute walk to best sunsets and whatever comes nextbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for allbrbrThe BeachbrAccess to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrListing includes two 2BR units in nearby buildings (total 4BR) and units are two flights up with no one above them. One unit has a king bedroom, a bunkroom with full over full bunk, and a sofa. A second unit has two queen bedrooms and a sofa. You can sleep up to 13 family style. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels, and the resort supplies chairs and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Private Vacation Home

Gertrude's Siesta | Pool, Jacuzzi! 1-minute to Beach! 4-min Dining & Music!

Siesta Key, Florida, United States

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Bath

Sleeps

$437.76

BEAUTIFUL apartment located directly on the No. 1 beach in the USA - Siesta Key! The apartment offers 2 bedrooms, living room with sofa bed and TV, fully equipped kitchen, two bathrooms with bath and shower, toilet, washing machine, tumble dryer. The dominant of the whole apartment is a balcony with a beautiful seaview. Crystal Sands also offers a private pool. Sarasota is 9 km from CRYSTAL SANDS. The nearest airport is Sarasota Bradenton International Airport, 16 km from the property.

Siesta Beach The BEST seaview from apartment

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$289.61

A beautiful 2-bedroom/2-bath fully appointed condo nestled into a the only true resort on Siesta Key. Enjoy being on the ground floor of the In-Demand F building with direct beach access! This condo affords you the ability to walk out your lanai door and be on the beautiful Siesta Beach within steps. This unit has a king size bed in the master bedroom with the master bath having a vanity and walk in shower as well as a walk-in closet. There are 2 twin beds in the guest bedroom, and the guest bathroom has a tub/shower combo. With its fully equipped kitchen and dining room that sits 6, you will have plenty of room for entertaining if you wish. It also has a laundry room with a washer and dryer. Take advantage of the properties state of the art fitness center, saunas/spas, 3 heated swimming pools, 8 tennis courts (2 converted for pickleball), shuffleboard, basketball/racquetball, tiki huts, grilling areas, 2 clubhouses, and if you like, Americas #1 beach is waiting just outside your door with some of the most spectacular sunsets on the planet. Welcome to Gulf and Bay Club!

Gulf and Bay Club- F105 Beautiful unit and great location!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$182.39

Drop your bags and start your vacation! This comfortable 2 bedroom/1 bathroom condo is an idyllic spot to relax. With a breathtaking view of the Bay, a community pool to enjoy, and a short distance to the beach, you'll truly have your own slice of paradise. This condo is just steps away from the grilling area, picnic tables and fishing pier. brMore amenities include tennis courts, billiard room, and clubhouse.brbrTop rated Siesta Key Beach is just minutes away--bike, walk (0.7 mile) or take the free shuttle!

Bay View Condo, Minutes to Top Beach in the US

Siesta Key, Florida, United States

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Bath

Sleeps

$485.03

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, a guest bedroom offering two twin beds as well as a sofa bed in the living area. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Apartment

Island House Beach Resort 9N

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$293.58

Gulf and Bay Club B309 by Tropical Sands Accommodations brCondo in Sarasota, Florida br brWelcome to Gulf and Bay Club B309! This stunning two-bedroom, two-bath condo is the perfect retreat for those seeking a home-away-from-home experience. You'll appreciate the comfortable accommodations, fantastic community amenities, and the close proximity to Siesta Key attractions. br brHighlights br• Gorgeous condo br• Washer and dryer in unit br• 2-minute walk to the beach br• Private Beach Access br• 3 Shared heated pools br• Shared Tennis, pickleball, Racquetball, basketball, and shuffleboard courts br• Shared Fitness Center br• Community electric vehicle chargers br• 5-minute walk to trolley stop br• 1.8 miles to Siesta Key Village br brGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the lakes. br brGulf and Bay Club B309 has been beautifully updated to feel like home from the moment you walk in. Large windows fill the bright, open living space with natural light. The spacious seating area features ample sofa seating and a flat-screen TV, while the modern kitchen is fully equipped with all the cookware you need. A dining table for four is ready for enjoyable meals. brbrThe primary bedroom boasts a King bed and an elegant ensuite bathroom with a double vanity, spacious closet, and walk-in shower. The second bedroom offers two comfortable queen beds. A full bath is located in the hallway, along with a washer and dryer for your convenience. Book your stay at Gulf and Bay Club B309 today and start your annual getaway tradition in paradise.

Recently Updated Condo Short Walk to Private Beach - Gulf & Bay Club B309

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$324.07

Gulf and Bay Club C701 by Tropical Sands Accommodations brCondo in Sarasota, Florida brbrWelcome to Gulf and Bay Club C701! This perfect two-bedroom and two-bath Siesta Key condo boasts stunning views of the community pools, a serene freshwater lake, and the breathtaking Gulf of Mexico in the backdrop.brbrHighlights br• Newly Renovated Beach Condo br• Screened-in lanai with stunning beach views br• Washer and dryer in unit br• Less than a 1-minute walk to the beach br• Private Beach Access br• 3 Shared heated pools br• Designated Reserved covered parking spotbr• Hi-Speed wifi and Xfinity Cablebr• Shared Tennis, pickleball, Racquetball, basketball, and shuffleboard courts br• Shared Fitness Center br• Community electric vehicle chargers brbrThis gorgeous corner unit on the top (7th) floor of the C Building is beautifully illuminated by natural light and stunning beach views. And by having an end unit, you also get to enjoy extra views out of your kitchen and living room windows to the side. It features a gorgeous seating area with a plush sectional sofa and a TV, along with a dining table set for six and ample seating at the kitchen island. The upgraded kitchen is equipped with stainless steel appliances and essential cookware, and the screened-in lanai’s outdoor table is the perfect spot for enjoying family favorites. brbrThe primary bedroom is beautifully decorated with nautical themes, featuring a comfortable King bed and beach views, along with an ensuite bathroom that includes a double vanity and a walk-in shower. The second bedroom offers two full beds and convenient access to the hall bath, which includes a shower and tub combo. For added convenience, a washer and dryer are available for guest use, making mid-vacation laundry a breeze.brbrGulf and Bay is a fabulous beachfront condominium complex with private beach access to Siesta Key Beach and its world-famous white sands and warm waters. This complex features three heated pools, saunas, a hot tub, activity courts for tennis, pickleball, racquetball, and shuffleboard, a fitness center, and numerous tiki-themed BBQ areas surrounding the lakes. Your dream vacation starts here - book now!

Beach Views! - Gulf and Bay Club C701

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$309.26

Welcome to this newly renovated and immaculate condo in Siesta Key is 1500 sq ft and can accommodate 6 guests. This perfect two-bedroom retreat features a king bed and two queen beds plus a cozy living room with a sofa bed for extra guests. With two full bathrooms, including a refreshing shower and a second bathroom with a tub, getting ready is a breeze. Our condo is located on the bay across the street from the beach. The community has 2 pools, tennis courts, pickleball, BBQ’s, and a gym. Our condo has a ping pong table in the garage. We also have a whole house filtration system for drinkable water.brIn the living room we have board games for the whole family.brIn the garage we have a beach cart, beach chairs, beach toys, boogie boards and umbrellas. We also have tennis rackets, pickleball rackets and balls to be used for our multiple courts during your stay.

Newly renovated and beautifully decorated 2 bedroom 2 bath condo

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$409.08

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin size beds, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Villa

Island House Beach Resort V18

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$303.84

Get ready to feel like royalty in this beautifully updated condo with expansive, unobstructed views of Siesta Key Beach and the Gulf of Mexico. Imagine waking up to the sound of waves, sipping your morning coffee while gazing at endless blue water, and ending each day with a sunset you’ll never forget. This is beach vacationing at its finest.brbrWith 2 bedrooms, 2 full baths, and 1,220 sq. ft. of living space, there’s plenty of room for everyone to relax.brbrMaster bedroom: two plush queen bedsbrbrGuest bedroom: two twin beds (can be joined to create a king)brbrWe’ve thought of everything: beach towels, linens, chairs, and an umbrella—all ready and waiting so you can travel light.brbrThe fully equipped kitchen makes family meals and impromptu dinners a breeze, while the screened-in lanai offers the perfect place to dine with panoramic Gulf views. After spending the day on the #1 beach in the U.S.—just 100 steps from your door, come home and unwind by the Olympic-size heated pool, or head to the grilling area for a relaxed cookout.brbrIf you want to stay active, our on-site fitness center has you covered. And when you’re ready to venture out, Siesta Key Village—with its restaurants, shops, and nightlife—is just moments away.brbrOur on-site management team is here to ensure your stay is effortless from start to finish.brbrPack your swimsuit and flip-flops—your perfect Siesta Key escape awaits.

Amazing Gulf Views 2 Bed 2 Bath at Siesta Key Beach Steps to Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$692.01

Blu Sky Cottage | Waterfront Pool Home, Resort-Style Backyard, Near Siesta Key Villagebrbr Why You'll Love This HomebrBlu Sky Cottage stands out for its rare combination of waterfront access and a resort-style backyard, offering a one of a kind setting on Siesta Key. The outdoor space is the true highlight, with a private saltwater pool and spa overlooking the canal, creating a seamless connection between relaxation and activity. The backyard is designed for both lounging and play, with space for outdoor dining, grilling, and games, all set against the water. With direct canal access, guests can utilize the complimentary kayaks and paddleboards, or bring a small boat and head out right from the property. Inside, the home features an open-concept layout with comfortable living and dining areas, along with a dedicated workspace complete with a printer for added convenience during longer stays.brbr ‍ ‍ Perfect ForbrFamilies or small groups looking for a waterfront stay with standout outdoor space, easy access to Siesta Key Village, and room to unwind between beach days.brbr ️ Imagine ThisbrSpend the morning out on the water, launching a paddleboard or kayak directly from the backyard. Return home to cool off in the pool or relax in the spa while overlooking the canal. Afternoons are easy here, grill lunch outside, gather around the shaded dining area, or play a casual game of cornhole in the yard. As the day winds down, head into Siesta Key Village for dinner or stay in and enjoy the quiet waterfront setting.brbr Where You'll Sleepbr• Bedroom 1: King Bedbr• Bedroom 2: King Bedbr• Bedroom 3: Queen Bed + Twin Bunk BedbrbrAccommodates up to 8 guests.brbr Explore the Areabr• 1.0 Mile to Siesta Key Beach – Powdery white sand and Gulf watersbr• 0.5 Miles to Siesta Key Village – Restaurants, shops, and nightlifebr• Canal Access – Paddleboarding, kayaking, and boating from the propertybrbr⌛ Don't WaitbrA rare Siesta Key find due to its waterfront setting and standout outdoor space, Blu Sky Cottage offers a resort-style backyard experience paired with a prime Siesta Key location. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to KnowbrPer Sarasota County regulations, this property allows one rental per 30-day period. Please contact us for more information. The pool is heated between November 15th and April 15th. Cooler temperatures may impact heating performance. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome 1 small dog (up to 25 lbs) with a $250 fee per pet—breed guidelines apply to ensure a safe and comfortable stay for everyone.

Private Vacation Home

Blu Sky Cottage | Waterfront Pool Home, Resort-Style Backyard, Near Siesta Key Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$223.11

Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 2nd Floor condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to the public beach access with provided beach chairs, towels, and cooler... everything you need to enjoy the pristine beach across the street. Located 1/2 mile from Siesta Key South-end Village with shopping, restaurants, and bars. If you are looking for even more selection, Siesta Key Village is also just 2 miles north. brbrStep inside and you will enter the main living area furnished with dining table with seating for 4 and the living room area furnished with comfortable lounge seating couches with a flat screen TV. The kitchen is fully equipped with fridge, stove, oven, dishwasher, and microwave. You will find that the home has all the cookware and dish-ware you need to make your stay comfortable. You can do your own laundry in this home, as there is a washer and dryer inside for your convenience! Around the corner you will find the guest bedroom and bathroom. The guest bedroom is furnished with queen-size bedroom set along with a twin to sleep your guests and family. The guest bathroom is equipped with tub/shower combo. Moving down the hall you find the master suite. The master bedroom is furnished with a king-size bedroom set and access to walk-in closet as well as the en-suite bathroom which is equipped with stall shower and double sink vanity. brbrThere is a handy free island trolley that runs the length of the island when you don't want to drive. You can also give a call to one of the free rides.brbrWhether it be a family vacation or just a romantic couple getting away on holiday or a much-needed vacation, you can't go wrong.brbrNo pets allowed at this community. No smoking permitted in the condo. One carport is provided with additional guest parking if needed.brbrBay Oaks has a minimum stay restriction of 7 days

Updated Siesta Key Vacation Rental at Bay Oaks

Siesta Key, Florida, United States

Bed

Bath

5

Sleeps

$387.15

Jamaica Royale Unit PH2 Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale Unit PH2, a beautifully updated two-bedroom, two-bathroom townhouse located just steps from the world-renowned Siesta Beach on Sarasota’s Gulf Coast. Recently refreshed with a coastal modern look, this spacious two-story retreat features flexible sleeping arrangements with trundle beds, bright open living areas, and private beach access. Ideal for families or small groups seeking the perfect Siesta Key getaway close to Siesta Beach, local dining, and the Siesta Key Village trolley.brbrHighlightsbr• 2 Bedrooms / 2 Bathroomsbr• 1 King bed with Twin trundlebr• 2 Twin beds plus Twin trundle in guest bedroombr• Washer and dryer in unitbr• 3 shared heated poolsbr• Private balconybr• Private beach accessbr• Community shuffleboard courtbr• Two community BBQ areasbr• Assigned parkingbrbrJamaica Royale offers guests a classic Siesta Key resort experience with direct private beach access to the soft quartz sand of Siesta Beach, consistently ranked among the top beaches in the United States. Spend your days lounging at one of the three heated swimming pools, grilling at the community BBQ areas, or enjoying a casual round of shuffleboard. Outdoor showers, tropical landscaping, and peaceful walking paths enhance the relaxed coastal setting.brbrPH2 features a bright and welcoming open concept layout with new furnishings, a comfortable living area, and sliding doors that invite natural light throughout the space. The fully equipped kitchen includes essential appliances, ample counter space, cookware, and everything needed for easy vacation meal prep. A cozy dining space offers seating for shared meals after a day on the sand, while the living room provides plush seating and a flat screen TV for unwinding in the evenings.brbrThe primary bedroom offers a restful retreat with a king bed and a twin trundle, plus closet storage and calming coastal decor. The guest bedroom is ideal for children or friends traveling together, featuring two twin beds and an additional twin trundle for flexible sleeping arrangements. One bathroom is conveniently located upstairs near the bedrooms, while a second bathroom downstairs provides added comfort for larger groups. Both bathrooms feature walk in showers and single vanity sinks.brbrRoom Detailsbr• Primary Bedroom (Upstairs): King bed + twin trundlebr• Guest Bedroom (Upstairs): Two twin beds + twin trundle (nearest the bedroom door)br• Bathroom 1 (Upstairs): Shared hallway bath, walk in shower, one vanity sinkbr• Bathroom 2 (Downstairs): Shared hallway bath, walk in shower, one vanity sinkbrbrUnit PH2 includes a washer and dryer, private balcony, Wi-Fi, cable TV, assigned parking, and access to all Jamaica Royale community amenities. Guests are within minutes of Siesta Key Village, local restaurants, beachfront cafes, outdoor recreation, bike rentals, and the free Siesta Key Breeze Trolley.brbrWith its refreshed interiors, flexible bedroom layout, outstanding community amenities, and premier location just steps from Siesta Beach, Jamaica Royale Unit PH2 offers an incredible opportunity to experience the best of Siesta Key. Book your stay with Tropical Sands Accommodations today and immerse yourself in the relaxed, sun-soaked lifestyle that makes this destination unforgettable.

Jamaica Royale Penthouse 2 Beachfront with Pool, Tennis, & Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$295.86

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.brAnchorage Resort Condo br2 bedrooms / 2 bathroomsbrSpacious Balcony overlooking Northern Siesta KeybrSixth Floor Condo overlooks Northern Siesta KeybrFully equipped Kitchen with seating for 4 at the dining tablebrBeach Supplies include- Beach Cart, Chairs, Umbrella, Cooler, Raft/Float Items, Beach TowelsbrCommunity Pool- Largest pool on the Key!brGated CommunitybrSiesta Key Trolley- free pickup in front of the resort entrancebrPrivate Beach access to Crescent Beach across the streetbrElevator br25-year minimum age to rent restrictionbrbrBEDROOMS (Sixth Floor Condo)brBedroom 1: One King Bed (Ensuite Bathroom) / Balcony Access / 42 TVbrBedroom 2: Two Queen Beds / Balcony Access / 19 TVbrbrThe Anchorage Resort Amenity Access Included with Rental:br* Olympic-Size poolbr* 3 Lighted Tennis/Pickleball Courtsbr* 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- Heated brbrResort 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 onlybrbrDistances 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. 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 6th Floor 2 bedroom Condo on Siesta Key

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$2486.0

Discover your dream retreat in this stunning Siesta Key beach house! With 6 bedrooms & 6.5 baths, this home is perfect for families or groups. Dive into the heated pool featuring a thrilling water slide, or unwind in the serene spa. Centrally located in vibrant Siesta Key Village, you’re just a short stroll from pristine beaches, delightful restaurants, and charming shops. Enjoy coastal lifestyle with modern amenities and an inviting atmosphere, making it an ideal getaway for relaxation and fun!brbrEnjoy your beach days with ease. We supply beach towels, beach chairs, and a wagon to make your trips to the shore effortless.brbrPool Heating DisclaimerbrbrPlease note that pool heaters are weather-dependent. When outdoor air temperatures drop below 55°F, electric pool heaters will not operate, and pool water will remain cold. Even when temperatures rise slightly above 55°F but stay in the low 60s, the heater may produce minimal heat and may not significantly warm the pool.brbrThe only way to guarantee a consistently warm pool during colder months is with a gas pool heater, which can operate in very low temperatures but requires substantial gas usage to maintain warmth.brbrBy booking during cooler months, guests acknowledge that pool temperature and heater performance are directly affected by weather conditions, which are beyond the control of the property owner or management. We strongly recommend reviewing and acknowledging this information prior to booking to ensure clear expectations regarding pool heating during your stay.brbrImportant Note:brWhen you stay at our vacation rental homes, we want to ensure your experience is comfortable and convenient right from the start. Each home comes with a thoughtfully prepared starter pack to help you settle in seamlessly. This pack includes:brbr- *Laundry Detergent*: Enough for your initial laundry needs.br- *Dish Soap*: For easy clean-up after meals.br- *Dish Sponge*: Essential for washing dishes.br- *Dishwasher Pods*: A few pods to kickstart your dishwashing.br- *Toilet Paper*: Two rolls per bathroom to get you started.br- *Paper Towels*: One roll for quick clean-ups.br- *Extra Trash Bags*: To accommodate your waste disposal needs.brbrPlease note that we do not provide used kitchen items like oil, spices, or butter, ensuring a fresh start for your cooking adventures. Additionally, all homes are equipped with drip coffee makers, but remember to bring your own coffee filters to enjoy your morning brew.brbrWith these amenities, you can focus on enjoying your vacation without the worry of running out of essential supplies.brbrEarly Check In & Late Check Out:brFrom February through August, we regret to inform our guests that early check-ins and late check-outs will not be available. This decision is due to a high volume of reservations during these peak months, which unfortunately limits our ability to accommodate flexible check-in and check-out requests. We appreciate your understanding and encourage you to plan your arrival and departure times accordingly. Thank you for your cooperation!

Private Vacation Home

New! Beach House with heated pool/spa water slide!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$480.93

NEW PHOTOS OF UPGRADES COMING SOON!!!brbrThis beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, a guest bedroom offering two twin size beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Apartment

Island House Beach Resort 17S

Siesta Key, Florida, United States

Bed