Key Amenities
About this property
Your dream vacation awaits! Your spacious and private single-level house is a perfect getaway for a peaceful and relaxing vacation. Enjoy all the comforts of home while being just a short walk away from bars, restaurants, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined ...
Property Type
Siesta Key House
Featured review
I've enjoyed three years in a row at Jonathan's wonderful Siesta Key house and hope to continue doing so for years to come. I've stayed at multiple rentals all over the country and nobody's home or hospitality ...
Key Amenities
About this property
This vacation rental condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. We are excited to announce that B108 has recently been ...
Property Type
Siesta Key Condo
Featured review
This is our third year in a row staying at Fishermans Cove. Our first year we were in a second floor condo these last two years we had ground floor and wouldn’t have it any other way. Everything is spotless, ...
Key Amenities
About this property
Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...
Property Type
Siesta Key Condo
Featured review
We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!
Key Amenities
About this property
Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6) If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...
Property Type
Siesta Key Condo
Featured review
Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean
Distance to beach: 20 yards to Crescent Beach, Siesta Key
Key Amenities
About this property
Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...
Property Type
Siesta Key Condo
Key Amenities
About this property
Escape to a tranquil oasis on Siesta Key! This charming studio unit boasts a queen-sized Murphy bed, perfect for a romantic getaway or relaxing retreat. Enjoy breathtaking pool views from the comfort of your own space, and step outside to find yourself mere steps away from the soft white sands and crystal-clear ...
Property Type
Siesta Key Condo
Key Amenities
About this property
CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...
Property Type
Siesta Key Condo
Featured review
The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...
Key Amenities
About this property
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 ...
Property Type
Siesta Key Condo
Featured review
We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...
Key Amenities
About this property
This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and new furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances including ...
Property Type
Siesta Key Condo
Featured review
We stayed on Turtle Bay and had a wonderful view of the Gulf from our second floor balcony. The condo was clean and the decor was fun to look at. They had so many extras available: laundry detergent, ...
Key Amenities
About this property
If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...
Property Type
Siesta Key Condo
Featured review
My husband and I intended to stay here in early February. On several occasions we reached out to customer service regarding damage from the hurricane. A letter was sent that only said “some amenities ...
Key Amenities
About this property
SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...
Property Type
Siesta Key Condo
Featured review
Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate
Key Amenities
About this property
This colorful custom2rd floor unit has a commanding view of the Gulf of mexico. This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit. From the modern kitchen, you will enjoy Siesta ...
Property Type
Siesta Key Condo
Featured review
Fisherman's cove is the ultimate spot for a peaceful getaway. Your host Carrie is a wonderful, warm and thoughtful person. You won't find anyone better. Her condo Is perfectly located on the corner of the ...
Key Amenities
About this property
A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...
Property Type
Siesta Key Condo
Featured review
I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...
Key Amenities
About this property
We lucked out! Hurricane Helene did not flood our beach house except for the carport. (But the Aloha Kai area is closed for the at least one month.) Hurricane Milton damaged some soffits. A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, ...
Property Type
Siesta Key House
Featured review
We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...
Distance to beach: 950 feet to Crescent Beach
Key Amenities
About this property
Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...
Property Type
Siesta Key Condo
Featured review
Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The ...
Key Amenities
About this property
CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...
Property Type
Siesta Key Condo
Distance to beach: 150 yards to Crescent Beach
Key Amenities
About this property
1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...
Property Type
Siesta Key Condo
Featured review
Due to Helena, our condo was cancelled. Would have loved to be there but understand why we couldn't. Best to the owners as they recover. I am giving 5 stars because this was not the fault of the owner.
Key Amenities
About this property
Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of ...
Property Type
Siesta Key Condo
Key Amenities
About this property
VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated Pool Located right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent Beach VILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...
Property Type
Siesta Key Condo
Featured review
The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.
Distance to beach: 100 feet to Crescent Beach
Key Amenities
About this property
Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA. This luxury 2 bedroom 2 bath apartment, has been kept up to date ...
Property Type
Siesta Key Condo
Featured review
Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.
Key Amenities
About this property
The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...
Property Type
Siesta Key Condo
Featured review
Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.
Key Amenities
About this property
CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...
Property Type
Siesta Key Condo
Distance to beach: 0.1 miles to Siesta Key Beach
Key Amenities
About this property
NEWLY UPGRADED - BEAUTIFUL CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South Village - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley. Sit on the balcony for a quiet and ...
Property Type
Siesta Key Condo
Featured review
The property has two rooms with their own bathrooms and it was perfect for what we needed. Choosing whether to spend time at the pool, beach across the street or playing pickleball, also across the street ...
Key Amenities
About this property
Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...
Property Type
Siesta Key House
Featured review
A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...
Distance to beach: 0.0 miles to Siesta Key
Key Amenities
About this property
Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak. Unwind in comfort ...
Property Type
Siesta Key Villa
Key Amenities
About this property
Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated 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 ...
Property Type
Siesta Key Condo
Distance to beach: 850 feet to Crescent Beach
Key Amenities
About this property
Direct-with-Owner Rental Discounts: Midnight Cove #532 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed ...
Property Type
Siesta Key Condo
Featured review
This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and ...
Key Amenities
About this property
NEWLY RENOVATED IN 2023!! VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS, VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...
Property Type
Siesta Key Villa
Featured review
I cannot tell you how amazing the property is! Half a mile walk to a gorgeous beach, a 5 minute drive to the #1 beach in the US, shopping close by, great restaurants, an amazing pool, wonderful outdoor ...
Key Amenities
About this property
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 ...
Property Type
Siesta Key Condo
Featured review
The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.
Key Amenities
About this property
My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets! The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...
Property Type
Siesta Key Condo
Featured review
This unit offers an amazing view of the ocean and sunsets. Perfect get away spot, great location, clean and has everything you need to enjoy your stay. We will be back in 2014!
Key Amenities
About this property
Welcome to Hemingway House, a charming retreat located on the northern end of Siesta Key. This delightful home offers a perfect blend of comfort and convenience, ensuring an unforgettable vacation experience. Just a short 5-minute walk will lead you to the serene shores of Shell Beach, where you can soak ...
Property Type
Siesta Key House
Distance to beach: 0.1 miles to Crescent Beach Siesta Key
$265
avg/night
Key Amenities
About this property
Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...
Property Type
Siesta Key Condo
Featured review
The place is absolutely beautiful. Great views and amenities! Close to walking distance to most things. Would definitely stay here again!
Key Amenities
About this property
Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with ...
Property Type
Siesta Key House
Featured review
The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience ...
Key Amenities
About this property
This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing ...
Property Type
Siesta Key Condo
Featured review
This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting ...
Distance to beach: 0.3 miles to Siesta Beach
Key Amenities
About this property
This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space with dining table and lounging area, living room, dining area, ...
Property Type
Siesta Key Condo
Key Amenities
About this property
You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...
Property Type
Siesta Key Condo
Featured review
Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...
Key Amenities
About this property
Comfortable and peaceful home with private saltwater pool and hot tub, 1.4 miles from the beach; 1 mile to the village. I have beach gear. Plenty of chairs, an umbrella, towels and coolers. Beautiful private back yard with grill and smoker in quiet neighborhood. Very comfortable and peaceful retreat. ...
Property Type
Siesta Key House
Key Amenities
About this property
Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.
Property Type
Siesta Key Condo
Featured review
We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.
Distance to beach: 0.2 miles to Siesta Key Beach
Key Amenities
About this property
Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...
Property Type
Siesta Key Condo
Featured review
Lovely 2B/2B ground floor condo with fabulous sunroom getting morning sunshine. Sunroom faces a shell path that winds throughout the development and views lush landscape with blooming hibiscus bushes. Quiet ...
Key Amenities
About this property
Updated 2 bedroom unit in charming Casarina complex is located directly on the crystal white sands of Siesta Key Beach. Amenities galore! Magnificent gulf views. Enjoy the serenity of this casual, comfortable and tastefully decorated home away from home. You will enjoy having the In unit laundry, ...
Property Type
Siesta Key Condo
Featured review
I absolutely loved my stay. The condo was impeccable and the sunsets were gorgeous. I highly recommend this unit. The master suite was so lovely. We really enjoyed the pool, spa, and trips to the Village.
Key Amenities
About this property
THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai. *Decorated in a "beachy motif" with granite counter tips in the kitchen ...
Property Type
Siesta Key Condo
Featured review
I highly recommend condo 601 South/ Beauty at the Beach! Elaine was very accommodating and her condo was the most coziest, beautiful, and relaxing place that I have stayed in a very long time. It had everything ...
Distance to beach: 200 yards to Crescent Siesta Key Beach
$244
avg/night
Key Amenities
About this property
Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...
Property Type
Siesta Key Condo
Featured review
Great place to stay! Has everything you need for a great beach stay. The condo was clean, decorated nicely, and offered beach supplies. It was only a short walk to the beach as well. The host was great ...
Key Amenities
About this property
This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...
Property Type
Siesta Key Condo
Featured review
I can't say enough about this property absolutely heaven out your front door is a beautiful Bay with manatees playing in it pretty much every day we were able to be there!! out the back door you're about ...
Distance to beach: 0.0 miles to Siesta Key Public Beach
Key Amenities
About this property
This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated updated condo, with newly tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...
Property Type
Siesta Key Condo
Featured review
We loved the beautiful condo. It was our first trip to Siesta Key and we enjoyed it thoroughly. The condo was well kept, fully furnished for the most part and the Mgmt team was there to help us when we ...
Distance to beach: 20 yards to Crescent Beach, Siesta Key
Key Amenities
About this property
Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...
Property Type
Siesta Key Condo
Featured review
Recently, we stayed at a Fisherman’s Cove for Spring Break. What a wonderful place to stay! Close to the ocean/beach and the condo had everything we needed!
Key Amenities
About this property
This charming Siesta Key vacation rental home offers a beautiful kitchen, dining area, living room, and outdoor patio. The property includes access to a heated pool shared between the two units in the house. Located in the heart of Siesta Key Village, it's just a 3-minute walk to the #1 beach in ...
Property Type
Siesta Key Apartment
Key Amenities
About this property
RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...
Property Type
Siesta Key Condo
Featured review
This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...
Distance to beach: 0.4 miles to Siesta Key Beach
Key Amenities
About this property
Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too! Canal home in heart of the Siesta Key Village, no need for a car! Steps away ...
Property Type
Siesta Key House
Featured review
The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar ...
Key Amenities
About this property
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 ...
Property Type
Siesta Key Condo
Featured review
These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.
Key Amenities
About this property
This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout. ...
Property Type
Siesta Key Condo
Featured review
Location was amazing - views spectacular, nothing separating us from the beautiful gulf. Condo - was missing nothing and needed nothing additional. Clean. Stocked. Convenient. Comfortable. Owners - ...
FAQ
