Siesta Beach Vacation Rentals, Condos & Apartment Rentals.
Vacation Rentals by Owner in Siesta Key Beach, Florida.
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Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale
Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL
Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the island of Siesta Key off Sarasota, Flori.......
Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
Villa Siesta sits poetically in a walled, gated garden on deep, azure-colored Hansen Bayou with views of Sarasota Bay & City skyline. This architecturally unique 5400 sf villa is built around a spacious tower with winding 3 story staircase opening to each living level.
The romantic residence is located just a few blocks from Shell Beach, less than 3 mi from award-winning Siesta Beach & short distance (less than 4 mi) to downtown Sarasota where restaurants, shops & cultural activities abou.......
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Located steps from the Gulf of Mexico, on the best part of the famous Crescent Beach. Our home offers beautiful full gulf views.
Welcome to our spacious, fully equipped condominium, minutes from great shopping, restaurants, and more! Recently remodeled kitchen. Many recent updates. Enjoy this beautiful, well-maintained condo in a peaceful setting. Our unit is on the fourth floor of a 4-story building with spacious vaulted ceilings offering spectacular Gulf views. Enjoy all the amenities Sies.......
Firethorn 611- 2-bedroom, 2-bath ground floor unit on Bay Side
Welcome to this newly remodeled 6 person, 2-bedroom, 2-bath ground floor unit on Bay Side with a lovely canal view! Enjoy a roomy kitchen which provides plenty of countertop and cooking space, along with all new cabinets and dining ware. Full second bathroom with a walk-in tile shower. New vinyl flooring and bright walls along with an extended living area makes this space airy and fresh. Full-size washer and dryer in unit, located in the hallway. A king size bed in the master bedroom and 2 twins.......
Luxury on Crescent Beach - Great Location!
Luxury condominium directly on world-famous Crescent Beach! Located at Siesta Breakers - one of the premier properties on Siesta Key. Enjoy this designer furnished unit - with quality flooring, cabinets, granite counter tops, kitchen appliances, two televisions, free wi-fi, and classic island-inspired furnishings. The property features a beautiful pool, two lighted tennis courts, and a community gas grill. It is conveniently located just across the street from bars & restaurants, a food market,.......
BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta Key
Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL
Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the island of Sies.......
Ground Floor at Bay Oaks in Siesta Key - Watch Dolphin in the Bay - Fish from the Pier. Unit E81
Nicely furnished ground floor condo located in the popular Bay Oaks resort on Siesta Key. Covered parking just steps from the unit. Living room has comfortable leather seating, with a queen sleeper sofa for additional sleeping. Both bedrooms have en-suite bathrooms, master comes with walk-in closet.Well stocked kitchen with dishwasher. Full size washer & dryer in the unit. Fully air conditioned, plus ceiling fans in every room. Free WiFi is provided in the unit as well as at the clubhouse. TV's .......
Newly Refurnished Tropical Townhouse - Watch Dolphin in the Bay, Fish from the Docks! Unit B62
Newly Refurnished Tropical Townhouse at Bay Oaks - Enjoy the large waterfront BBQ/Picnic area and fishing piers on the bay as you watch for dolphin in the bay waters!
Newly refurnished unit offers 2 floors of living space featuring 2 patios and a screened in lanai for plenty of outside space. New flooring, no carpet. Downstairs is the spacious living room with comfortable new furnishings including a queen sleeper sofa & views of tropical landscaping and mature trees. Adjoining the living .......
Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205
Welcome to our condo 8/205. Featuring beautiful wood floors, Siesta Dunes 8-205 is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing evenings and memorable chats under the stars. Our condo has two bedrooms, two bathrooms, and can sleep six. It is in the garden area, and is one of the largest end units, with .......
Firethorn 322-Beachfront 2BR/1.5BA condo on gorgeous Siesta key
2nd floor, (stairs) Beachfront 2BR/1.5BA. King bed in master, 2 twins in guest bedroom. Washer and Dryer in the unit. Cable TV, phone, complimentary wi-fi and a Keurig coffee maker. AMAZING full view of the beach! Extended living area goes all the way out to the glass sliders, (unit does not have an outdoor sitting area.) Only a short walk to the pool or beach where there are beach loungers and an umbrella waiting for you! Tennis court on property, grilling/picnic areas, fitness room across the .......
Stunning 3 Bedroom Home with Roof-Top Pool on Siesta Key!
This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 1nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and enjoy the breathtaking views from the incredible rooftop pool!
The Space:
Bedroom 1: King
Bedroom 2: King
Bedroom 3: Queen bunk
L.......
9.2 Star Review
3 Bedrooms
- Sleeps 10
Siesta Key Vacation Rental
Pet Friendly 
Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key!
This must-see home on Siesta Key offers a much sought after modern and contemporary design. With plenty of space for the entire family. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. Complete with a full kitchen, living, and dining space, make this place your home away from home and enjoy the breathtaking views from the incredible rooftop pool!
The Space:
Bedroom 1: King
Bedroom 2: King
Bedroom 3: Queen bunk
L.......
8.8 Star Review
3 Bedrooms
- Sleeps 10
Siesta Key Vacation Rental
Pet Friendly
Modern 3 Bed/2.5 bath Gulf Side Condo Steps from Siesta Key Village and Beach!
Newly renovated in 2025, this modern beachfront condo offers breath-taking beach views and a straight walk to the sugary white sand and crystal-clear water! With 3 bedrooms, 2.5 bathrooms, this home comfortably sleeps 6. Wake in the master bedroom’s king size bed to enjoy the Gulf views from your own private balcony. In the second bedroom, is a queen size bed with another balcony and in the third bedroom is another queen size bed, featuring a large walk-in closet. Only a 5-minute walk to Siest.......
Screened Balcony Living | Bayfront Siesta Key | Sunrise Views & Easy Beach Access at Bay Oaks
Welcome to the Bay Oaks on the Bay!
Enjoy your Siesta Key getaway in this 3rd-floor Bay Oaks condo with 2 bedrooms, 2 baths, and great amenities in a relaxing bayfront setting. Stroll to beach access #12 or hop on the free Siesta Key Breeze Trolley, then return to sunsets on the Gulf or sunrises over the bay. Perfect for a comfortable stay near it all!
LOCATION HIGHTLIGHTS:
- 7-minute bike ride to Siesta Key Beach
- 14-minute walk to Crescent Bea.......
New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104
This ground floor 2 bedroom, 2 bathroom unit is nicely updated and comfortably furnished with easy access to the pool and the beach. Our Property is managed by the Siesta Dunes Rental Office and the staff is available to assist you during your stay.
Amenities include:
Gulf View, from 1st Floor
King in Master Bedroom
Shower in Master Bathroom
2 Twins in Guest Bedroom
Shower/Tub in Guest Bathroom
Tile Flooring Throughout
DVD, Stereo and CD Pl.......
Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale
Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL
Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the island of Siesta Key off Sarasota, F.......
Siesta Key Home, Heated Pool, Spa, near the beach! - Talk To The Sand
Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!
Talk To The Sand by Siesta Key Luxury Rental Properties
Home in Siesta Key, Florida
Your dream vacation awaits at Talk To The Sand, a spectacular home with a fabulous backyard, a hot tub, pool, a waterslide, and a rooftop deck where you can have private sunset Gulf viewings! With seven bedrooms and seven and a half bathrooms, this pet-friendly rental is the ultimate getaway for.......
9.6 Star Review
7 Bedrooms
- Sleeps 14
Siesta Key Vacation Rental
Pet Friendly
Stunning Sunset Views-Steps to Siesta Key Beach-A Couples' Romantic Beach Condo
WAKE UP TO FULL PANORAMIC GULF VIEWS. FALL IN LOVE WITH SIESTA KEY.
A Beach Condo With Over 125 5-Star Reviews
Imagine waking up each morning to breathtaking panoramic views of the sparkling Gulf waters, stepping into your private enclosed lanai with a fresh cup of coffee, and watching the gentle waves roll onto the world-famous white sands of Siesta Key Beach.
Now imagine ending every day with a front-row seat to breathtaking spectacular sunsets, as the sky transforms into brillia.......
3 BR house+ heated pool in huge private yard. 12min walk to beach. Pet friendly.
Enjoy this private pet friendly house with your own swimming pool, in beautiful Siesta Key. Oversized private lot. Renovated main bathroom and master bathroom. Custom designed high end rain showers. ** HEATED POOL ** (up to 84 degrees December to April). Walk to Crescent Beach or beach access 10 - Walk to the North Village or ride bikes. This well maintained vacation home comes fully equipped with all the amenities you could want and possibly some you did not think about. Master Bedroom has Ki.......
10.0 Star Review
3 Bedrooms
- Sleeps 6
Siesta Key Vacation Rental
Pet Friendly
NEWLY REMODELED! On World Famous Crescent Beach
Condo was fully remodeled in the summer of 2020 complete with beautiful new flooring. Kitchen was completely redone with new cabinets, quartz countertops, and all Stainless Steel appliances.
TV's in both bedrooms
Two new Recliners in Living Room
55" HD LED TV with DVR and Blu-ray Player in LR
King bed in Master Bedroom
Futon in Master Bedroom
Two single beds in Guest room
Queen pull out in Living Room
Shower in Master Bath
Tub an.......
Stunning Siesta Key Beach Views from 2 Bedroom Condo!
Experience panoramic views of the Gulf, Siesta Key Beach, and stunning sunsets, from this beautifully updated 6th-floor corner condo. Enjoy 12 foot floor-to-ceiling sliding doors that open to two spacious balconies, creating the perfect island retreat. Just a 1–2 minute walk to world-famous Siesta Beach, with access to a heated pool, tennis and pickleball courts, and a covered pavilion with grilling area. Siesta Key Village is just minutes away for shopping, dining, and entertainment.
T.......
Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key!
Wake up to ocean breezes at Coastal Surfside, a stunning three-bedroom island escape on Siesta Key. With a full private kitchen, large dining space, and cozy living room, this multi-level home is perfect for families or friends looking for their perfect vacation home! Step onto your private balcony, grab a beach wagon and complimentary gear, then explore the pristine shoreline just steps away, or venture out to discover the charming Siesta Key Village.
The Space:
Bedroom 1- King
Be.......
Buttonwood 447- 3 bedroom 2 bath condo with fantastic view of gulf
Fabulous 3 bedroom 2 full bath, full gulf view unit! The unit is on the 4th floor in a 7 story building. Approximately 1600 Sq. ft. of living space. Master bedroom features King bed, large walk-in closet, with view of beach and glass sliders out to the screened lanai. Master bath has dual sinks and large, gorgeous stone walk-in shower. The first guest bedroom features 2 twin beds, 5 drawer dresser and big closet, plenty of room and flat screen TV. The second guest bedroom features a full size be.......
Firethorn 330- Fabulous direct beachfront 2br condo
FABULOUS DIRECT BEACHFRONT 2BR CONDO...180 DEGREE PANORAMIC VIEW! Updated and modern/beachy condo with granite counter tops, custom cabinetry, new furniture and porcelain tile throughout. All NEW Stainless Kitchen Appliances. 2BR/1.5BA with new washer/dryer, open balcony with stunning gulf views for the perfect sunset...Tommy Bahama decor, and so much more! The view is among the best at Midnight Cove! Living room features Large Flat Screen TV and DVD. Master bedroom includes new Queen Bed & flat.......
Chinaberry 473-2 bedroom/2 bath with fantastic Gulf of Mexico and Crescent Beach views
Full and fantastic Gulf of Mexico and Crescent Beach views from this seventh floor 2 bedroom/2 bath 1400+ sq. ft. unit! Enjoy the Siesta sunsets from the spacious screened lanai and listen to the sleepy sounds of the surf from the master bedroom! Living room offers a sleeper sofa, flat screen TV/DVD. Master bedroom has king size bed with TV. Master bath features walk in shower. Guest bedroom has twin beds, TV. Guest bath includes a tub/shower combination. Washer & Dryer. Phone/Wifi. Unit accommo.......
Buttonwood 462 -Magnificent 6th floor, quiet, end/corner unit w/over 1600 sq. ft. of spacious living
Magnificent 6th floor, quiet, end/corner unit with over 1600 sq. ft. of spacious living space. The unit is a 3 bedroom 2 full baths. Master bath has large walk in shower with dual sinks. Guest bath is tub/shower combo. Tile flooring through the entire unit except the larger guest bedroom with queen bed which is carpet. Light and bright tasteful d?cor. The 3 bedrooms have wall mounted TVs and a large 50" TV in the living room. Fabulous view of Crescent Beach and the sparkling aqua blue water of t.......
Beautiful 4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Beach Front Home on Siesta Key's Sunset Beach! This Beautiful home comes equipped with a full kitchen, a dining area, and a spacious living room for you to spend time with your family and friends. Enjoy spectacular sunsets and the white sand beach right outside the front door! It’s only a short stroll into Siesta Key Village for all of the wonderful shops and restaurants the island has to offer and with views like this, this vacation home is sure to be your choice returning year after year!
8.4 Star Review
4 Bedrooms
- Sleeps 12
Siesta Key Vacation Rental
Pet Friendly
Chinaberry 415-Great ground floor, gulf side 2 bed/2 bath unit.
Great ground floor, gulf side 2 bed/2 bath unit. The screened lanai opens right out just a few steps from the pool and beach featuring the famous, award-winning, soft, sugary-white sands of Crescent Beach on Siesta Key! Relax on the furnished lanai while enjoying views of the Gulf of Mexico and beautiful tropical grounds of Midnight Cove! New leather sofa features two recliners facing large tv and a love seat with full size sleeper sofa bed and TV/VCR/DVD. Large kitchen and dining area. Master b.......
Doveplum 121- 2 bedroom 2.5 bath Beachfront condo
NEWLY REMODELED BEACHFRONT CONDO!!! This 2 story (2nd/3rd level unit, enter stairs to 2nd floor main living/kitchen area)- 2 bedroom, 2.5 bath unit has 2 full master suites upstairs with their own bathrooms and walk in closets. Downstairs has a large and spacious fully remodeled living room, remodeled dining room, remodeled half bath and a brand new all remodeled, fully equipped eat-in kitchen! All new stainless steel appliances, all new wood laminate flooring throughout, all new furnishings and.......
Chinaberry 413-Ground floor 2/2 with slider glass enclosed lanai for a little more privacy.
Ground floor 2/2 1400+ sq. ft. with slider glass enclosed lanai for a little more privacy. Open the sliders and still get the screened lanai effect and experience the cool tropical breeze from the Gulf of Mexico. Kitchen (featuring a Keurig coffee maker) and baths have granite counter tops and all flooring is covered in ceramic tile. Walk to pool and the white sands of Crescent Beach right from your back door! Living room offers a 42" HD TV. Master bedroom has king bed with TV and the master bat.......
Firethorn 311- Beachfront, ground floor 2BR/1.5BA unit
Beachfront, ground floor 2BR/1.5BA unit. Sit and watch the gorgeous sunset from your ceramic tiled screened-in lanai, just steps to the beach! Fully carpeted living & bedrooms. Kitchen features custom cabinets and meganite countertops. Master bedroom has a King bed and T.V. Master bath features a walk-in shower with a built in seat and glass doors. Guest bedroom has 2 twins and T.V. Unit has Washer & Dryer and Wi-Fi. Heated Pool, Private Tennis Court, Fitness Center, Clubhouse with Computer, Pri.......
Chinaberry 455-Beautiful 5th floor 2 bed/2 bath unit with spectacular view of the Gulf
Beautiful 5th floor 2 bed/2 bath unit with spectacular view of the Gulf of Mexico and Crescent Beach! Spacious lanai is glass/screen enclosed. Master bedroom features a king bed with TV and master bathroom has a walk-in shower and dual sink vanity. Guest bedroom includes two sets of bunk beds: Twin over Queen and Twin over Twin. Guest bath has a step in shower. Washer & Dryer in unit. Phone/Wifi. Unit accommodates up to a maximum total of 6 people........
Firethorn 111- Gorgeous, fully remodeled 2BR/2BA beachfront
Gorgeous, fully remodeled 2BR/2BA! Step right out your back door to the soft, white, sugary sand of world famous Crescent Beach! You are so close to the Gulf of Mexico in this gulf front unit! Tastefully decorated and you can watch the sunset right from your screened lanai! Fully remodeled kitchen with ALL NEW appliances! The master bedroom is furnished with a queen size bed and TV. The master bath has a tub/shower combo. The guest bedroom is furnished with a brand new queen size bed and a full .......
Buttonwood 432-3BR condo with partial Gulf view, pool, private beach access, and 2 baths.
Over 1600 sq. ft. of spacious living space and ceramic tile throughout; beautifully decorated. The living area features a large flat screen TV and DVD player, the kitchen is adorned with granite counter tops, stainless steel appliances and a Keurig coffee maker. The master bedroom features a king bed a flat screen TV; master bath has dual sink vanity and a large step in shower with tiled seating. The first guest bedroom offers a queen bed and a flat screen TV; guest bathroom has a shower. The th.......
Doveplum 621- Newly remodeled and refurnished 2BR/2.5BA townhome
Fantastic, newly remodeled and refurnished 2BR/2.5BA townhome, multi-level (stairs) 2nd & 3rd floor unit overlooking a canal. Entire condo recently re-painted, new blinds, new living room furniture including a new sleeper sofa couch. Newly Updated Kitchen with all new stainless steel appliances. New Blue Ray DVD player/Flat Screen TV in living room! Dining room seats 6. Keurig Coffeemaker. Glass/Screen Enclosed Lanai off of the living room has all new furniture and is newly carpeted. Both bedroo.......
Firethorn 310- 2bedroom 2 bath beachfront condo short walking distance to restaurants
TOTALLY RENOVATED 2024! Step outside the spacious screened lanai of this ground floor unit to the soft sugary sands of Crescent Beach. It's like having the beach in your own back yard! Ceramic tile floors throughout. Beautifully decorated living room has Flat screen TV & DVD. Kitchen features custom cabinetry, granite counter tops and stainless steel appliances. Master bedroom features a king size bed with Flat screen TV and the master bath offers a tub and shower combo. Guest bedroom has Flat s.......
Find the Top Vacation Rentals in Siesta Key, Sarasota Florida.
We have 2,3 or 4 Bedroom beachfront Condo Rentals with ocean view or a Beach House for the entire family. Book Direct Here!
Siesta Key Beach consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. Located close to Sarasota, an eight-mile barrier island with stunning natural beauty, this award-winning beach is known for its pristine sugary white sand that is often described as the finest in the world. Vacation Rentals near Siesta Beach, Turtle Beach and Crescent Beach area are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.