Vacation Condo Rentals By Owner In Siesta Key, FL

$263.56

Midnight Cove II 923C - Coastal Condo with Views in Siesta Key

Siesta Key, Florida, United States

Welcome to Midnight Cove II 923C! Siesta Key is a laid-back destination filled with an array of shopping, dining, art, and culture. Experience the convenience of the free Siesta Key Breeze Trolley, allowing you to explore the area without worrying about parking. Enjoy a leisurely stroll to the beach via our dedicated access and indulge in the blissful sand-in-your-toes experience at Siesta Beach, renowned for its beautiful quartz-white sand and voted #1 in the US multiple times by Tripadvisor.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis beautiful 2-bedroom, 2-bathroom condo offers amazing views of the pool and boat lagoon. The primary bedroom features a comfortable king bed, while the second bedroom is equipped with two twin beds—perfect for families or friends looking to unwind together. brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II today and immerse yourself in Siesta Key's beauty! Your ideal getaway awaits!

2

Bed

2

Bath

4

Sleeps

$263.56

/ Nightly

Condo

Midnight Cove II 922C - Siesta Key Condo with Water Views with Pool and Tennis

Siesta Key, Florida, United States

Welcome to Midnight Cove II 922C! Siesta Key is a stunning island brimming with shopping, dining, art, and culture, making it the ideal vacation destination. Enjoy the convenience of the free Siesta Key Breeze Trolley, eliminating any parking hassles while you explore the village. Take a leisurely stroll to our dedicated beach access and treat yourself to the delightful sand-in-your-toes experience at Siesta Beach, celebrated for its sugar-fine quartz-white sand.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Waher and dyer in unitbr• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis beautifully decorated two-bedroom, two-bathroom condo boasts picturesque views of the lagoon, lush grounds, and the Intracoastal Waterway. The primary bedroom features a king bed, while the guest bedroom offers two twin beds, making it perfect for families. The living room includes a sleeper sofa for extra guests, accommodating up to six people comfortably. You'll also appreciate the convenience of an in-unit washer and dryer, enhancing your stay. brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrLocated just minutes from downtown Sarasota and attractions like the renowned Ringling Museum of Art, Midnight Cove II is the perfect setting for your getaway.brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II today and discover your dream beach retreat! Your slice of paradise awaits!

Bed

Bath

Sleeps

$263.56

/ Nightly

Condo

Midnight Cove II 912C - Beautiful Sunrise Views! Ground-level Siesta Key Condo

Siesta Key, Florida, United States

Welcome to Midnight Cove II 912C! Situated in the heart of Siesta Key, our community offers a delightful mix of shopping, dining, art, and culture that is sure to entertain you. Enjoy the complimentary Siesta Key Breeze Trolley, which takes the worry out of parking while you explore the picturesque village. Take a pleasant stroll to the beach via our dedicated access point, where you can sink your toes into the warm sand and rejuvenate by the sparkling Gulf waters.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis tastefully appointed first-floor unit features 2 bedrooms and 2 bathrooms, complete with a washer and dryer for your convenience. Step out onto your lanai to take in the beautiful views of the Intracoastal Waterway, where you’ll feel the tranquility surrounding you. The primary bedroom offers a comfortable queen bed, while the guest bedroom features two twin beds, perfect for family or friends. The inviting living room is equipped with a queen sleeper sofa, accommodating extra guests effortlessly.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrLocated just minutes from downtown Sarasota and attractions such as the renowned Ringling Museum of Art and Walt Disney World, Midnight Cove II is the perfect setting for your next getaway. brbrReady to experience the beauty of Siesta Key Book your stay today and discover why this is the ideal destination for relaxation and joyful memories!

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Bath

Sleeps

$245.17

/ Nightly

Condo

Midnight Cove II 611F: Ground-floor Bayside Condo with Access to Pool and Beach

Siesta Key, Florida, United States

Escape the northern chill and experience the ultimate Florida retreat at Midnight Cove II 611F! This first-floor condo is perfectly situated in the heart of Siesta Key, America’s #1 beach destination. Enjoy easy access with no stairs—just 60 feet from your parking spot and only 40 feet from the private heated pool, offering options for sunbathing or shade.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrThis freshly updated 1,010 sq ft condo features 2 bedrooms and 2 bathrooms, a spacious kitchen and dining area, plus a cozy family room complete with a pull-out couch. For added convenience, you’ll find a laundry room equipped with a washer and dryer. Relax and unwind while enjoying peaceful views through floor-to-ceiling sliding glass doors that open to a small grassy area overlooking the pool.brbrTake a leisurely walk to the docks along the serene Intracoastal Waterway or stroll to the famous Siesta Key Beach via private access. Known for its powder-soft quartz-white sand, Siesta Key Beach is consistently ranked as the best in America. Discover a private beach closet stocked with essentials like chairs, toys, and a wagon for a fun day by the shore.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrExploring Siesta Key is effortless! Hop on the FREE Siesta Key Breeze Trolley to visit The Village, filled with dining, shopping, and entertainment. We’re just minutes away from downtown Sarasota and the renowned Ringling Museum of Art, and conveniently located 10 miles from Sarasota Bradenton Airport, with easy access to Orlando’s theme parks and Tampa Bay’s sports venues.brbrBook your stay at Midnight Cove II today and immerse yourself in the sun-soaked charm of Siesta Key! Your perfect vacation awaits!

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Bath

Sleeps

$311.71

/ Nightly

Condo

Midnight Cove II 620D - Tropical Condo in Siesta Key

Siesta Key, Florida, United States

Welcome to Midnight Cove II 620D! Stroll to the beach via our dedicated access point and indulge in the sand-in-your-toes experience at the world-renowned Siesta Beach, famous for its sugar-fine, quartz-white sand.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrLocated minutes from downtown Sarasota and attractions like the Ringling Museum of Art, as well as driving distance to Walt Disney World and Busch Gardens Tampa Bay, Midnight Cove II is the perfect retreat for your vacation.brbrThis lovely three-bedroom condo boasts Tommy Bahama-style furnishings and stunning views overlooking the swimming pool and lush landscaping. The primary bedroom features a king bed, the guest bedroom includes a twin bed, and another guest bedroom is furnished with a queen bed, comfortably accommodating families or groups.brbrReady to pack your bathing suit and flip flops Book your stay at Midnight Cove II today and experience the unforgettable charm of Siesta Key!

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Bath

Sleeps

$311.71

/ Nightly

Condo

Midnight Cove II 520 D: 2-Bedroom Townhouse Steps from Crescent Beach!

Siesta Key, Florida, United States

Welcome to Midnight Cove II 520 D! This inviting townhouse features 2 bedrooms and 2 bathrooms, making it the ideal retreat for families or couples seeking a relaxing getaway on Siesta Key. Just steps from the beautiful white sand of Crescent Beach and close to local shops, dining, and cultural attractions, you’ll find everything you need for a memorable vacation.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Siesta Key Beach and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, the spacious living room is furnished with a comfortable sectional sofa and modern beach decor, perfect for unwinding after a day in the sun. The well-equipped kitchen features an island bar for casual dining. The primary bedroom boasts a queen bed and a private balcony, while the guest bedroom offers two twin beds, ideal for kids or friends. A bonus queen sofa in the living room provides additional sleeping space for larger groups.brbrReady to experience the ultimate beach retreat Book your stay at Midnight Cove II 520 D today and create lasting memories in this tropical oasis! Your dream vacation awaits!

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Bath

Sleeps

$439.4

/ Nightly

Condo

The Ocean View at Sandy Cove

Siesta Key, Florida, United States

Best sunsets in Florida at the pier. brbrPrivate beachfront grounds or easy walk to Siesta Key Village. brbrGround floor newly renovated condo with large private patio, lanai, pond with ocean and fountain view, heated pool, grill, private beachfront grounds, fishing pier, and clubhouse.brbrModern luxury 3 bedroom 2 bath condo with open floor plan, 4 sets of sliders, stainless appliances, quartz counters, bar, ice maker, drink fridge, High end drinking water filter and whole house water filtration.brbrPrivate access to the condo, lanai and large 60 foot patio with 8 person outdoor dining table, lounge areas, umbrella and Weber grill.brbrCommon grounds include heated pool area, pond, fishing pier, clubhouse, and private beachfront grounds for swimming, fishing, lounging, dining, kayaking, dolphin, manatee and bird watching.brbrI am available for whatever you want. Just call or message me for recommendations or anything you may need.brbrSandy Cove is a private beachfront oasis for residents of Sandy cove only. Right next to and easy walk to famous Siesta Key VillagebrbrFree taxi services, trolleys, private and guest parking. Easy walk to Siesta Key Village and private beachfront groundsbrbrSandy Cove is one of the most beautiful and serene waterfront properties on Siesta Key. Known to be the best fishing on the key. Access only for residents and guests of Sandy Cove.

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Bath

Sleeps

$270.66

/ Nightly

Condo

Pet-friendly condo a short walk from private beach & fishing dock on bay

Siesta Key, Florida, United States

Get your second wind at A Second Wind! Roomy, quiet and comfortable third-floor condo at beautiful Island Reef. Beach-to-bay complex on the peaceful side of Siesta Key with a pool view. Our private Gulf beach, pools and bay are not crowded at all. Two heated pools, tennis courts, pickleball and sauna. The private beach is just a five-minute walk across two-lane Midnight Pass Road with a crosswalk light. Boat dock and kayak put-in on bay side. Mature community and a calm, quiet atmosphere that makes it easy to relax in peace! The master bedroom has a king size bed with a spacious walk-in closet, flat screen TV and computer workstation with monitor and powerful wifi -- work from the pool! The guest bedroom has two twin beds, a wall-to-wall closet and a flat screen TV. There is a stackable washer and dryer in the utility room. Beach cabana, towels and chairs provided. Dedicated covered parking spot near the entrance. Walk to Ophelia's or Turtles Restaurant. Free public trolley to Siesta Key Village and its quaint shops and great restaurants. Sarasota's awesome museums & restaurants as well as upscale shopping at St. Armands are just a few miles away. Oh, and the sunsets are breathtaking! NOTE: Because of demand and HOA limitations, there is a 3-month minimum for high season (Jan-March).

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Sleeps

$1327.89

/ Nightly

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Gertrude's | 100% Private Resort-like home & pool, 500ft to private Siesta Key beach access!

Siesta Key, Florida, United States

Onyx Villa - Siesta Keybr100% Private! Resort-like home only 500ft to private beach and Siesta Key's whitest sand. Private amenities include - fully appointed pool area, alfresco dining and lounging, in-house elevator, open sun and covered balconies, and 4-hole putting green, and wraparound sunset view balcony! Includes two units on one private property. Perfect for families or couples wanting to experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway at this Siesta Key vacation rental now! brbrWhat Guests Lovebr∙ 100% Private – freestanding home and all its amenities are totally privatebr∙ Balconies – balconies off bedrooms, living, diningbr∙ The Beaches – 1-min walk to Siesta Key's whitest sand and calmest waterbr∙ Pool – heated with sun-shelves, chaises, dining, and grillbr∙ Views – westerly wraparound balcony with sunset viewsbr∙ Relaxing – Open floor plan, elevator, and balconies off every bedroombr∙ The Putting Green – 4-holes, no green fees, course record: 06br∙ Sunsets –walk 1-min to worlds best sunsets or just enjoy from balconies or poolbr∙ Free Trolley – 1-min walk to free trolley destined for island's top shopping, dining in Siesta Villagebr∙ Restaurants – walk bike or ride trolley to 30 dining options within 1-2 milesbr∙ Point of Rocks Reef – walk snorkel or paddle searching shells, dolphins, manateesbr∙ Memories and Fun - live music, daiquiris, oysters, stone crab, craft beer, ice creambr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrOur Siesta Key beach access is only a 500ft walk on a quiet lane and has the whitest sand and calmest water on the island. You can walk south 1-mile to explore Point of Rocks Reef or just swim or wade to any nearby sandbar. The water is shallow and clear with white quartz-sand tide-pools perfect for sleeping drinking or playing. You'll go from the water and sand, back your unit for lunch or dinner without putting on your shoes.brbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities this property will deliver what they are searching for. At the house you'll enjoy a private pool, poolside grilling and dining, 3200 ft.² of private balconies, and multiple alfresco lounging areas perfect for your bonding and relaxing enjoyment. Outside the house it's a 1-min walk left to the best beach on the island and 1-min walk right to the free trolley stop to all the top attractions on the island including two marinas, 30 bars and restaurants, shopping, live music, and countless eco-adventures.br brbrBedroom DetailsbrThis is a large property with two 3BR units for a total of 6BR. You can sleep up to 20 family style and every bedroom opens to a private balcony. The penthouse sleeping - The master suite has a king bed with bath en-suite. Bedrooms #2 and #3 have king beds and share a convenient guest bathroom. The living area features a full sized Murphy bed. The lower unit sleeping – The master suite has a king bed with bath en-suite. Bedroom #2 with a king bed and #3 with a twin over king bed and twin trundle share a convenient jack and jill bathroom. Two twin Tempur-pedic rollaway's are also available with advance notice. Twin Tempur-pedic rollaway's are also available with advance notice.brbrProperty TruthsbrThe unit is advertised as “100% private,” and you will never share the home with other guests. Occasionally—typically about once per week—the pool or landscaping service may stop by for routine maintenance. These visits are quick, limited to exterior or storage spaces, and always completed during daytime hours.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, 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 ProvidedbrThis vacation rental comes with 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.

Bed

Bath

Sleeps

$696.37

/ Nightly

Condo

NEW LISTING! Gertrude's | Resort-like home & pool, 500ft to Beach!

Siesta Key, Florida, United States

The Onyx Unit 1 - Siesta KeybrResort-like unit only 500ft to private beach access and Siesta Keys whitest sand. Amenities include - fully appointed pool area, alfresco dining and lounging, in-house elevator, open sun and covered private balconies, and 4-hole putting green, and wraparound sunset view balcony! Perfect for families or couples wanting to experience Siesta Key's top attractions without sacrificing space and comfort. Book a vacation now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ Private Balconies – private balconies off bedrooms, living, diningbr∙ The Beaches – 1-min walk to Siesta Key's whitest sand and calmest waterbr∙ Pool – heated with sun-shelves, chaises, dining, and grill (1-unit shares)br∙ Views – private westerly wraparound balcony with sunset viewsbr∙ Relaxing – Open floor plan, larger rooms, and balconies off every bedroombr∙ The Putting Green – 4-holes, no green fees, course record: 06 (1-unit shares)br∙ Sunsets –walk 1-min to worlds best sunsets or just enjoy from balconies or poolbr∙ Free Trolley – 1-min walk to free trolley destined for island's top shopping, diningbr∙ Restaurants – walk bike or ride trolley to 30 dining options within 1-2 milesbr∙ Point of Rocks Reef – walk snorkel or paddle searching shells, dolphins, manateesbr∙ Memories and Fun - live music, daiquiris, oysters, stone crab, craft beer, ice creambrbrThe BeachbrOur beach access is only a 500ft walk on a quiet lane and has the whitest sand and calmest water on the island. You can walk south 1-mile to explore Point of Rocks Reef or just swim or wade to any nearby sandbar. The water is shallow and clear with white quartz-sand tide-pools perfect for sleeping drinking or playing. You'll go from the water and sand, back your unit for lunch or dinner without putting on your shoes.brbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities this property will deliver what they are searching for. At the house you'll enjoy a semiprivate pool (1-unit shares), poolside grilling and dining, 1600 ft.² of private balconies, and multiple alfresco lounging areas perfect for your bonding and relaxing enjoyment. Outside the house it's a 1-min walk left to the best beach on the island and 1-min walk right to the free trolley stop to all the top attractions on the island including two marinas, 30 bars and restaurants, shopping, live music, and countless eco-adventures.br brbrBedroom DetailsbrThis is a large 3BR, you can sleep up to 10 family style, and every bedroom opens to a private balcony. The master suite has a king bed with bath en-suite. Bedroom #2 with a king bed and #3 with a twin over king bed and twin trundle share a convenient jack and jill bathroom. Two twin Tempur-pedic rollaway's are also available with advance notice.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, 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.

Bed

Bath

Sleeps

$582.73

/ Nightly

Condo

NEW LISTING! Gertrude's | Penthouse + Pool, 500ft to Private Beach

Siesta Key, Florida, United States

Onyx Penthouse - Siesta Key Vacation RentalbrResort-like penthouse only 500ft to private beach access and Siesta Keys whitest sand! Amenities include - fully appointed pool area, alfresco dining and lounging, in-house elevator, open sun and covered private balconies, and 4-hole putting green. This is a top floor unit with 14ft ceilings and wraparound ocean view balcony (partial view)! Perfect for families or couples wanting to experience Siesta Key's top attractions without sacrificing space and comfort. Book a vacation now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ Private Balconies – covered and open sun options off bedrooms, living, diningbr∙ The Beaches – 1-min walk to Siesta Key's whitest sand and calmest waterbr∙ Pool – heated with sun-shelves, chaises, dining, and grill (1-unit shares)br∙ Views – private westerly wraparound balcony with partial ocean and sunset viewsbr∙ Relaxing – Open floor plan, larger rooms, and balconies off every bedroombr∙ The Putting Green – 4-holes, no green fees, course record: 06 (1-unit shares)br∙ Sunsets –walk 1-min to worlds best sunsets or just enjoy from balconies or poolbr∙ Free Trolley – 1-min walk to free trolley destined for island's top shopping, diningbr∙ Restaurants – walk bike or ride trolley to 30 dining options within 1-2 milesbr∙ Point of Rocks Reef – walk snorkel or paddle searching shells, dolphins, manateesbr∙ Memories and Fun - live music, daiquiris, oysters, stone crab, craft beer, ice creambrbrThe BeachbrOur beach access is only a 500ft walk on a quiet lane and has the whitest sand and calmest water on the island. You can walk south 1-mile to explore Point of Rocks Reef or just swim or wade to any nearby sandbar. The water is shallow and clear with white quartz-sand tide-pools perfect for sleeping drinking or playing. You'll go from the water and sand, back your unit for lunch or dinner without putting on your shoes.brbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities this property will deliver what they are searching for. At the house you'll enjoy a semiprivate pool (1-unit shares), poolside grilling and dining, 1600 ft.² of private balconies, and multiple alfresco lounging areas perfect for your bonding and relaxing enjoyment. Outside the house it's a 1-min walk left to the best beach on the island and 1-min walk right to the free trolley stop to all the top attractions on the island including two marinas, 30 bars and restaurants, shopping, live music, and countless eco-adventures.brbrBedroom DetailsbrThis is a large 3BR, you can sleep up to 8 family style, and every bedroom opens to a private balcony. The master suite has a king bed with bath en-suite. Bedrooms #2 and #3 have king beds and share a convenient guest bathroom. The living area features a full sized Murphy bed and two twin Tempur-pedic rollaway's are available with advance notice.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, 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.

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Sleeps

$315.5

/ Nightly

Condo

Siesta Key Beach Escape

Siesta Key, Florida, United States

Siesta key beach is consistently one of the top three beaches in the USA. My condo is within view of the beach and short walk to the quaint little village. This roomy end unit has two large bedrooms, each with its own bath and walk-in closet. The living room has a queen sofa bed and there's a large lanai. Walk the beach, jump in the salt water pool at the condo, use the exercise room, or walk to the village for shopping and restaurants. No matter what you do you'll enjoy this magical place.

2

Bed

2

Bath

5

Sleeps

$334.54

/ Nightly

Condo

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key, Florida, United States

Come vacation in this first floor, quiet and recently remodeled unit. New bathroom, mattresses, bedding, paint, hardware, lighting, etc. Kitchen is fully equipped with all necessary cooking appliances. Unit is very clean and comfortable. brbrOnce you enter the community, it feels like a small neighborhood of it's own. It's one of the most family friendly and safe communities on the key with 2 NEW designated Pickleball Courts! We are a gated community, 5-10 minute walk across the street to private beach access and a full car garage.

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Bath

Sleeps

$289.87

/ Nightly

Condo

Charming Siesta Key Village Vacation Condo - Unbeatable Location, Free WiFi

Siesta Key, Florida, United States

Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed and professionally decorated with attention to detail and visitor comfort.The unit is fully furnished with most everything you will need for your stay on Siesta Key. There is even a washer/dryer inside the unit for your convenience! It is professionally managed by a local property management company that is available during your stay to make sure your visit is exceptional. You are just 200 steps to the powdery white sands that Siesta Key is famous for. You are also just 100 steps to the center of the Siesta Key Village, where you will find wonderful shops and restaurants to visit. The unit is a 1/1 with a queen sleeper sofa and sleeps 4 comfortably. Come stay at Siesta Key, where the beach was voted # 1 Beach in the USA by Dr. Beach in 2011.

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Bath

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$282.43

/ Nightly

Condo

Private Balcony, Community Amenities, Beach Access! Our House at the Beach W-203

Siesta Key, Florida, United States

Our House at the Beach W-203 by Tropical Sands Accommodations brCondo in Siesta Key, Florida brbrWelcome to Our House at the Beach W-203! This charming two-bedroom, two-bath condo offers all the comforts of home and community amenities! brbrHighlights br• Private beach access br• Screened-in balcony br• Washer and dryer br• Community pool br• Two Tennis Courts brbrInside, you'll find a beautifully decorated living space, complete with a coastal seating area, dining area, and a fully equipped kitchen featuring stainless steel appliances. Step onto the private balcony furnished with lounge chairs for soaking up the sun and enjoying drinks with loved ones. The primary bedroom boasts a King bed and an ensuite bathroom with a walk-in shower, while the second bedroom is perfect for kids with two twin beds and easy access to the hall bath with a shower and tub combination. Plus, guests have the convenience of a washer and dryer. brbrOur House at the Beach is located directly across the street from Siesta Key Beach, home to mesmerizing white sands and unforgettable Florida sunsets. This complex is set around a scenic lake and features a private community pool, a covered pavilion area with a BBQ, a picnic area, and two tennis courts for guests to enjoy.

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Bath

Sleeps

$297.88

/ Nightly

Condo

Midnight Cove II 733F - Updated Bayside Siesta Key Condo with Shared Amenities

Siesta Key, Florida, United States

Welcome to Your Private Oasis at Midnight Cove II 733F! This beautifully remodeled third-floor bayside condo offers exceptional privacy and a serene escape, featuring unobstructed views of the stunning lagoon and our family-friendly heated pool. Enjoy 1,000 square feet of living space that comfortably sleeps four guests, complete with 2 bedrooms and 1.5 bathrooms, spacious closets, and an amazing kitchen equipped for preparing family dinners or delightful appetizers before dining out at nearby restaurants.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrStep onto the private lanai to take in picturesque sunrises that greet you each morning. The cozy family room invites relaxation after a day of beach adventures. This home is fully stocked with fresh linens, beach towels, and even beach chairs and a buggy for easy transport to the world-renowned Siesta Key Beach, just a short stroll away via our dedicated access.brbrOur community boasts fantastic amenities, including two tennis courts (one for pickleball), a basketball court, a clubhouse, a barbecue area, and a beautiful observation deck along the intercostal waterway, perfect for watching dolphins and boats drift by. brbrExplore local attractions with ease! Use the free Siesta Key Breeze Trolley to reach The Village for dining, shopping, and entertainment, or take a day trip to Sarasota’s renowned Ringling Museum of Art. brbrBook your stay with us today and experience the ultimate getaway in paradise!

2

Bed

1

Bath

4

Sleeps

$344.49

/ Nightly

Condo

Our House at the Beach W-302 Warm and Inviting!

Siesta Key, Florida, United States

Just across the street from the acclaimed #1 Beach in the US. This beautiful 2 bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a heated pool, tennis courts and a covered pavilion with grilling area.

Bed

Bath

Sleeps

$316.54

/ Nightly

Condo

Our House at the Beach E-603 Phenomenal Views and Location

Siesta Key, Florida, United States

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities include a heated pool, tennis courts and a covered pavilion with grilling area.

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Bath

Sleeps

$233.62

/ Nightly

Condo

Midnight Cove II 510F - Siesta Key Beach Condo Rental with Community Amenities

Siesta Key, Florida, United States

Welcome to Midnight Cove II 510F! This charming first-floor condo offers 2 bedrooms and 2 bathrooms, making it the perfect retreat for families or friends seeking a beach getaway on Siesta Key. Located just a short walk from the beach and conveniently close to the heated pool, this inviting unit features fun beach decor and a comfortable living room, perfect for movie nights after a day of sun and sand.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrEach bedroom is furnished with a queen bed, ensuring a restful night's sleep. The two bathrooms include one with a shower-tub combo and the other featuring a walk-in shower. brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrPack your bags and book your stay at Midnight Cove II today! Experience the best of Siesta Key living and make unforgettable memories in this beachside haven!

2

Bed

2

Bath

4

Sleeps

$229.83

/ Nightly

Condo

Midnight Cove II 431F - Bay View!

Siesta Key, Florida, United States

Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming with shopping, dining, art and culture. Ride the Siesta Key Breeze Trolley â€œ it's FREE and find relief knowing you wonâ„¢t be driving around the village searching for a parking spot. Take a stroll to the beach via our dedicated beach access and enjoy a little sand-in-your-toes experience. Our Bayside property provides views of the Intracostal waterway while also being within walking distance to the Gulf of Mexico. Our property offers a heated swimming pool with a large pool deck complete with lounge chairs and seating with sunshade, 2 tennis courts with 1 of them having pickle ball lines, basketball court, club house, barbecue grilling area, a beautiful observation deck at the end of our property and even private docks available to rent for your boat. During season (February and March) we have popular events that include live music, Yoga classes and much more. We are located just minutes from beautiful downtown Sarasota, the world-renowned Ringling Museum of Art, as well driving distance to such attractions as Walt Disney World and Busch Gardens Tampa Bay. Sarasota is a top vacation destination in Florida and Midnight Cove II offers the perfect location and setting to enjoy it. We truly are the perfect location for your getaway. World acclaimed Siesta Beach is made famous by its sugar-fine, quartz-white sand, not to mention the thriving Siesta Village. Visit us and you will see why Siesta Key should be on your bucket list. Siesta Key beach has been ranked the best beach in America. Ready to pack up that bathing suit and a pair of flip flops If you're looking for a condominium rental, look no further! Our sprawling tropical oasis can accommodate a minimum 7-night rental to, well, forever if you like! So, welcome aboard and let us help you begin your accommodation planning! Maybe you want to stay forever and have found your happy place Check out our website for a listing of units for purchase. We have an agent on site that can assist you in the purchase of one of our fabulous Vacation Condominiums.brbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). br br This cute and cozy 3rd Floor, 2-bedroom, 1.5-bathroom condo sleeps four people. It has a great view of the canal and is a short walk to the pool, tennis courts and beach.

2

Bed

1

Bath

4

Sleeps

Vacation Condo Rentals By Owner In Siesta Key, FL

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$289.87

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$344.49

$316.54

$233.62

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