Home Vacation Condo Rentals By Owner In Sarasota, FL

Showing 1060 Of 1190 Vacation Rentals
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Exceptional(3)

$323.94

/ Nightly
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Siesta Key beach 3rd floor best location, walk to beach, shopping and dinning

Sarasota, Florida, United States

Come and make this private and secluded condo JUST STEPS from siesta key your home away from home! With BRAND NEW furniture throughout your guaranteed a clean and peaceful stay! Located on the second floor WITH an elevator, this condo is equipped with large cathedral ceilings and waterfront views of lake Sabal. This location is great for explorers looking to enjoy shopping and dining all within a walking distance including Captain Curts, Daiquiri Deck, CB’s saltwater outfitters and boat rentals, orange octopus ice cream, Claytons Siesta Grille and TONS more! Enjoy quick convenient access on and off the key as this condo is located only .4 driving miles from the south bridge off of a private and secluded dead end road (meaning no traffic!)brbrI have lived in 4 locations on Siesta key and this is by far the best area of them all. Nestled between the intracostal waterway and the gulf I love the privacy and seclusion this location offers and I know you will too. I enjoy being able to walk to many different dining and shopping option walking out to the beach. Also if you plan on making a trip off the island this is the best location on the key with the shortest time to the bridge.brbrIf you have any questions about our house or neighborhood feel free to ask we are here to help you! To see an in depth tour of our home CLICK HERE:”
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Exceptional(1)

$275.83

/ Nightly
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Siesta Key 2BR Condo • Pool - Intercoastal

Sarasota, Florida, United States

Feel the smooth warm sand between your toes as you enjoy a cold tropical daiquiri at our beautifully remodeled 2-bedroom Sandy Toes Condo, Siesta Key. 10- minute walk to Siesta Key Beach. Located just across the south bridge from Siesta Key, Sandy Toes Condo is in the highly desirable Castel Del Mare, welcoming guests to the best of both Siesta Key and mainland Sarasota. The Sandy Toes Condo is a 2 bedroom, 1.5 bath, 2 story walk-up which has been fully remodeled in 2022, featuring new furnishings and an in-house washer and dryer. Enjoy evening drinks on the private screened in Lanai or the open patio located directly off the master bedroom.brbrSandy Toes Condo is in the Castel Del Mare Condominium complex located directly across the south bridge from Siesta Key. Castel Del Mare features 2 swimming pools, one of which is directly on the Inter-Coastal Waterway, tennis and pickle ball courts, and shuffleboard. Castel Del Mare has beautiful views of the inter-coastal waterway including from a mangrove walk and gazebo. A quick 5-minute walk brings you to restaurants and shops. You can hear the steal drums playing from the Boatyard Waterfront Grill from your patio.brbrSiesta Key Beach access is located a quick 10 minute 1/2 mile down Stickney Point Rd to Crescent Beach at beach access #12.brbrThe location of Sandy Toes Condo is ideal for those traveling during peak season. The off island location allows for quick in and out access of the condo, avoiding the traffic of crossing Stickney Point Bridge onto Siesta Key.brbrKey Featuresbr10-minute walk to the beachbrIn-House Washer and Dryerbr2 Large community swimming poolsbrScreened in LanaibrFully Stocked KitchenbrbrPet Policy:brSandy Toes Condo is pet friendly for 1 Dog up to 25lbs. An Additional $250 pet fee will be applied to reservations with a pet. brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbrCome to enjoy Siesta Key in true luxury, and find out why Sarasota is one of the world's top travel destinations.brbr**Minimum Age 25: All Reservations must be booked by and accompanied by an adult who is 25 years of age or older. Valid photo I.D. may be required at the time of booking.
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Exceptional(3)

$267.15

/ Nightly
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Book Me Baby! Wildflower Inn Siesta Key #8 Coconut

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #8 CoconutbrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(5)

$267.62

/ Nightly
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Book Me Baby! Wildflower Inn Siesta Key #6 Bird of Paradise

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #6 Bird of ParadisebrMax of 1 Pet with $150 Pet Fee Added After BookingbrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(2)

$268.3

/ Nightly
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Book Me Baby! Wildflower Inn Siesta Key #7 Split Leaf

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #7 Split LeafbrMax of 1 Pet with $150 Pet Fee brbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(2)

$275.9

/ Nightly
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Book Me Baby! Wildflower Inn Siesta Key #5 Pineapple

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #5 PineapplebrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brLet's Head to the Beach!brConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(2)

$282.74

/ Nightly
Condo

Book Me Baby! Wildflower Inn Siesta Key #3 Orchid

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #3 OrchidbrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(2)

$282.74

/ Nightly
Condo

Book Me Baby! Wildflower Inn Siesta Key #4 Frangipani

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #4 FrangipanibrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brLet's Head to the Beach!brConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(4)

$282.75

/ Nightly
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Book Me Baby! Wildflower Inn Siesta Key #2 Hibiscus

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #2 HibiscusbrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brResort HighlightsbrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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Exceptional(2)

$139.51

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Resort living at Siesta Key

Sarasota, Florida, United States

Come relax and enjoy the serene setting with three water views. From the living room, bedroom, and lanai there are water views of the pool, intercoastal, and the Gulf of Mexico. Large, screened lanai with glass doors if air conditioning preferred. Open, full-sky views of the sunset. Enjoy the charm of this upscale one bedroom, one full bathroom condominium. Furnished with all required for a relaxing visit by the water and at the beach. Bedroom includes one King size bed with plush memory foam mattress topper, water views, and walk-in closet. There's also a queen-size Murphy bed in the living room. Features a large, screened lanai with glass doors, so if prefer you can choose air conditioning to watch the boaters, kayakers, wildlife, and sunsets. Located at the quiet end of Siesta Key it is a great place to relax and absorb the sunrays. Swim in the large, heated pool and enjoy the company of very nice people or cherish your privacy. Short walking distance to Turtle Beach, top quality restaurants, cycle (2 adult bikes included), or take the free trolley to famous Siesta Key Beach and Village for local festivities and entertainment. Head out over the bridge to the mainland for even more restaurants and entertainment with top name performers at the theater or live music. Enjoy local golf, sports activities and attractions. Two-person kayak available for use on site with nearby parks and private beaches.
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$281.44

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Book Me Baby! Wildflower Inn Siesta Key #1 Bromeliad

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You to The Wildflower Inn Siesta Key!brSuite #1 BromeliadbrMax of 1 Pet with $150 Pet FeebrbrYou have found the best kept secret on Siesta Key! Tucked among the lush, tropical foliage on picturesque Canal Road, this charming collection of 8 one-bedroom units stands waiting to serve as the memorable backdrop on which to paint your next vacation memories. As a curator of fine vacation rentals along Florida's Gulf Coast, it was Pinkie Flamingo's sworn duty to seek out the best “guest nests” she could find and serve them up to those who could truly appreciate the finer things in life….like unforgettable vacations, top-rated beaches and sunshine.brbrYou have found your own little slice of paradise.br“Shhhh… It's a secret!”brbr“I heard the owner has been making a lot of updates here” said Pinkie as she literally hopped from The Village in the heart of Siesta Key “I can't wait to see!” Completely renovated 2025 with all new everything…be among the first to enjoy the fresh new furnishings and décor. Adorned with vibrant tropical flora, each of the 8 guest suites surround a common courtyard that features a sparkling, seasonally heated pool. Ambiance abounds with the sights and sounds of the bubbling waterfall as guests relax after a day at the beach. Resort access includes 2 screened common areas with amenities galore! “I have never seen such a nice set-up!” Pinkie exclaimed.brbrLet's Look Around!brbrResort HighlightsbrSteps to the Beach (3 Min Walk to Access #10)brWalking Distance to The VillagebrSeasonally Heated PoolbrHot TubbrWaterfallbrOutdoor ShowerbrGame RoombrWide Screen TVbrPool TablebrPing Pong TablebrMs. Pac Man Arcade GamebrPopular GamesbrFire PitbrPool RestroombrPropane GrillbrBeach Carts Loaded with Backpack ChairsbrBeach UmbrellasbrPool/Beach ToysbrFloats/NoodlesbrCommon Area Laundry RoombrDock Access to Siesta Key Grand Canal with Kayak LaunchbrbrLet's Check Out The Rooms!brbrEach of the 8 guest suites features tropical décor and is named for a different wildflower. Finding your favorite will be a labor of love. Suites 1-4 are on the ground floor and suites 5-8 are on the upper level requiring steps.brQueen Size Master Bedroom with Smart TVbrComfy Living Area with Smart TVbrQueen Size Fold Out Sleeper SofabrModern Full Bathroom with Walk-In ShowerbrFully-Stocked KitchenbrBoth Keurig & Reg Drip Coffee-MakerbrDining Table Seats 4brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops….all within walking distance.brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…Plus 2 Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More
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$568.5

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Unit 31- 2 Bedroom 2 Bathroom Condominium With Gulf Front Views

Sarasota, Florida, United States

Unit 31- 2 Bedroom 2 Bathroom Gulf Front Condominium. ***This unit is a strict 7 night minimum*** This absolutely stunning completely renovated two bedroom two bathroom condo is located on the third floor of our Grande Tower Building. The amazing direct gulf front views from this unit allow you to enjoy our beautiful sunsets! Possibly sighting a manatee, or the dolphins playing in the surf. Because of its location, it is a short stroll to our white quartz beach and the azure waters of the Gulf of Mexico. This beautifully decorated condominium is perfect for a Siesta Key vacation. The spacious master bedroom has a king size bed with a 40 flat screen TV, and the guest bedroom has two queen size beds with a 40 flat screen TV. To comply with the Sarasota County fire code, the maximum number of guests permitted to sleep in this unit is six. The large living room is equipped with a 65 flat screen TV with Direct TV service for your enjoyment. The master bathroom has a walk-in shower and the guest bathroom has a shower/tub combination. The open plan kitchen has granite counter tops, all stainless steel appliances and an abundance of cabinets. It is fully equipped with all the items you need for cooking - pots/pans, dishes, utensils, toaster, coffee maker. The condo is completely tiled throughout. The furnished enclosed patio with sliding windows, allows you to enjoy our warm tropical breezes.
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$277.11

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Luxe Waterfront Resort Style Living at its Best!

Sarasota, Florida, United States

Summary:brWith only 5 minutes to Downtown Sarasota and 10 minutes to the beach you can easily spend the day poolside at the condo, take a waterfront stroll on the property's boardwalk and be off to dinner on St Amands and sunset at the beach all in one day!brThis property even offers 2 EV chargers, a full fitness gym, and fire pit lounge area!brbrThe Space:brInside the condo you have the convenience of working at the comfortable desk that affords you the space you need to work remotely. brWith extra guests the large queen sleeper sofa even has electronic shades for sleeping bliss and privacy.brOpen the veranda doors to the outdoors and enjoy the scenic waterway and all the abundant water and aquatic life Sarasota waterways have to offer! Take a sip of Sarasota Waterfront paradise!brbrGuest Access:brYou and your guests will have access to a gated resort community on the water. The pool and spa tub offer ample lounge chairs and seating beside the fitness center with bathrooms for guests as well. The unit also has a private covered garage parking space with extra parking in visitors parking. Bring your kayak and paddle board! The community offers a private ramp and private community walking boardwalk on the waterfront! The firepit area is set up lounge like and there is a grill area as well or you can use the private grill on the condos balcony. brNo need to rent beach chairs or a beach umbrella they are all provided with your stay!brbrThe Neighborhood:brDowntown Sarasota, Lido Key, Longboat Key, Siesta Key all a short distance to your tropical adventures!brbrOther Things to Note:brTravel with confidence. The #PMIPurify program is implemented in every rental, providing a pristine clean for all guests.brbrPlease note once you book you will be directed through to our pre arrival check-in process. Travel Protection Insurance is offered, but optional.brbrThis vacation property is part of a Community Association and requires a separate application submission, at no cost to you.  PMI Sarasota will process the application for you.brbrThis unit has a Ring Doorbell.brbrCANCELLATIONS, CHANGES, AND REFUNDS. brAll bookings are subject to the following cancellation policy:brbr1. PMI Sarasota Permitted Cancellation Periods:bra. 30 days or more prior to your check-in date for rental periods of 7 days or lessbrb. 60 days or more prior to your check-in date for rental periods of 8 days or more brbrYou may cancel your booking according to either a. OR b. above, given by written notice (email accepted with time-stamp) to PMI Sarasota. If the cancellation meets the criteria of either a. or b. the full amount of your reservation deposit will be refunded, less a $200 cancellation fee and any non-refundable charges including booking fees and management/admin fees.brbr2. All refunds, whether in whole or pro-rated, will be subject to the deduction of third party non-refundable charges.brbrFor cancellations made after the Permitted Cancellation Periods above, Guest is responsible for the full amount of the total booking charges. Guest’s only recourse for refund after the Cancellation Period is a claim on a previously purchased vacation travel insurance policy. To protect against loss of your advance deposit or booking payment resulting from cancellations caused by certain unforeseen events, such as illness, death, natural disasters, etc., we recommend that guests purchase Vacation Travel Protection Insurance.brbrbrSTARTER SUPPLIES: We offer a starter supply of toiletries and cleaning/laundry supplies.
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$346.3

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Unit 148 - 2 Bedroom 2 Bathroom Gulf Side Interior Club Condominium

Sarasota, Florida, United States

This completely renovated third/top floor 2-bedroom 2-bathroom condominium is located on the Gulf side of our property, in the Club building closest to our white sand beach. Because of its central location, #148 is also a short walk to the tennis courts, fitness center, pool and charcoal grills. This condo has everything you need to enjoy your Siesta Key vacation. The master bedroom has a king-size bed with a 65 TV, and the guest bedroom has two full-size beds and a 43 TV. The beautiful master bathroom has a walk-in shower, and the guest bathroom has a shower/tub combination, both with grab bars. The living room is equipped with a large 65 wall mounted, flat screen HDTV and a Bluetooth Bose speaker so you can listen to your favorite tunes. The newly renovated kitchen has granite counter tops and stainless-steel appliances and is fully equipped with all the items you need for cooking - pots/pans, dishes, utensils, toaster, coffee maker, Keurig machine, and even a wine refrigerator. The owner has provided a beach cart for ease in transporting your beach gear, as well as a rolling cooler that will keep your beverages ice cold. The condo is completely tiled throughout. The screened-in patio allows you to enjoy our beautiful tropical breezes while you sip your morning coffee, and the washers/dryers are located just downstairs in this building. The free, public trolley on Siesta Key, which travels back and forth between Siesta Village and Turtle Beach, has a stop near Palm Bay Club's front entrance. To comply with the Sarasota County Fire Code, our two-bedroom units sleep a maximum of six people.
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