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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. ...
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
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. ...
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 - ...
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Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. A306 is on the third floor and the views are stunning! Our community ...
Featured review
We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...
Key Amenities
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VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...
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.
Key Amenities
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Welcome to your slice of paradise in Siesta Key! Our updated 2-bedroom, 1-bath villa is just two villas away from the private, powdery white sands of Crescent Beach, ranked the #1 beach in the U.S. by both Dr. Beach and TripAdvisor. Enjoy complimentary cabanas and lounge chairs while soaking up the Florida ...
Featured review
The Villa was perfect for my December trip to Siesta Key! Very clean, appreciated lots of towels (which I find a plus staying other places they skimp on them), kitchen well equipped. Access to the beach ...
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Key Amenities
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Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may ...
Key Amenities
About this property
Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level ...
Featured review
This place is one of a kind. It has everything you need. Our family rents out the entire place every couple years. The location is amazing...right by the village and beach. The rooms are clean and bug free!!! ...
Distance to beach: 5 feet to Crescent Beach
Key Amenities
About this property
FULL GULF FRONT- Cathy's Crescent Condo-Beautiful turnkey 2nd floor condominium located on the pristine beaches of Siesta Key, FL. Voted the finest sand in the world. It doesn't get any better than this! This condominium is Full Gulf Front. You can view the water/beach while lying in bed from ...
Key Amenities
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This stunning, fully remodeled 2-bedroom, 2-bathroom Siesta Key condo offers the ultimate beachfront escape. Located on the serene south end of Siesta Key in Fisherman’s Cove, the condo faces the Gulf of Mexico and is just 100 feet from the water. Enjoy beautiful new tile flooring, a gourmet kitchen ...
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 ...
Featured review
Nice to deal with the rent of the property , I will book again .Very easy and simple self explanation
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, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may ...
Distance to beach: 0.1 miles to Crescent Beach Siesta Key
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, new state of the art pickleball and tennis ...
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
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may be some ongoing construction ...
Featured review
These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.
Key Amenities
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Gorgeous totally remodeled 2 bed (both brand new kings) 2 full bath condo in the highly desirable gated Gulf and Bay Club on the world-renowned Siesta Key Beach, a luxury community sitting on 32 acres and offering 3 pools, a fitness center, pickleball, tennis, saunas, hot tub, and its own 800 ft of private ...
Key Amenities
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Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!
Key Amenities
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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 ...
Key Amenities
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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 LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the world ...
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
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may be some ongoing construction ...
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
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 ...
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 ...
Distance to beach: 0.0 miles to Siesta Key beach also know as "Crescent Beach"
Key Amenities
About this property
Best beachfront view on Siesta Key from remodeled two bedroom and two bathroom beachfront condo. Stay for the unbelievably beautiful beachfront balcony views. Enjoy the modern open floor plan with beach views from most rooms. Beautifully furnished apartment you will be proud of.Upgraded, secure WiFi.Spectacular ...
Featured review
Hello I was looking to see if you had any last minute availability for February ? Sorry to contact through the review I could not find an email address to send a request. Thank you for your time best Joann
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 ...
Featured review
We had a great time and our rental was as described. Had everything we needed and communication was excellent throughout our stay.We will rent here again in the future and highly recommend!
Distance to beach: 0.1 miles to Crescent Beach on Siesta Key
Key Amenities
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This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling ...
Featured review
We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...
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This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart ...
Featured review
Midnight Cove is a great location and a beautiful property. The townhouse is beautiful and centrally located. The beach has the softest sand and an umbrella and two chairs are provided for each condo ...
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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)! ...
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!
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. New hurricane windows and door installed in 2024. Updated Kitchen fully remodeled with premium appliances. ...
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
Welcome to the gorgeous 2BR 3Bath beachfront townhouse nestled in the tranquil complex on Siesta Key, FL. Escape the big-city crowds and enjoy the lovely ambiance from the patio while being just a few steps from the pristine sandy beach, swimming pool, local restaurants, shops, and attractions. 2 Comfortable ...
Distance to beach: 0.1 miles to Siesta Key
Key Amenities
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Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky ...
Featured review
I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps ...
Distance to beach: 0.5 miles to Siesta Beach access 7
Key Amenities
About this property
*Calendar month rentals only*May-November (three-month lease) - $2900 per month plus utilities December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior for monthly ...
Featured review
I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...
Distance to beach: 400 feet to Siesta Beach
Key Amenities
About this property
Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor ...
Featured review
Our recent stay at the Siesta Key Beach Vacation Home was nothing short of incredible! The 3-bedroom home is ideally located from the world-renowned Siesta Key Beach, making it easy to enjoy the soft white ...
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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, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...
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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 ...
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. ...
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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 ...
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, ...
Distance to beach: 200 yards to Crescent Siesta Key Beach
Key Amenities
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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 ...
Featured review
Sandy, the owner was excellent with communication! I appreciated how immaculate and comfortable the condo was. The condo lacked nothing! Home away from home! The location of the condo provided a peaceful ...
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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 ...
Featured review
I could not have been more pleased with my stay and the communication with the owner. The apartment was spotless upon arrival and well stocked. Our family had an amazing time and will be returning for sure! ...
Distance to beach: 0.3 miles to Crescent Beach
Key Amenities
About this property
Discover the ultimate Siesta Key getaway with this beautifully appointed 3-bedroom Townhouse, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation and adventure ...
Featured review
I spent two nights at this place and I really enjoyed it! Everything was clean, washed and neat. All appliances were in working order and clean. It’s located very close to the beach and there is a common ...
Distance to beach: 0.3 miles to Siesta Key Beach access 10
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About this property
*Calendar month rentals only*******SPECIAL - April 2025 - $150 per night plus utilities - 10-night minimum****May - November (three-month lease) - $2000 per month plus utilities December - $3900 per month plus utilities January, February, & March- $6500 per month plus utilities April - ...
Featured review
I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...
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 ...
Featured review
The place was very clean. The location was perfect for beach trips and trolleys for visiting the village.
Key Amenities
About this property
Newly fully luxuriously decorated beach Townhouse is just a few steps from the private white sandy US #1 rated Siesta Key Beach. This 2 bedroom 2.5 bath is everything you want and more! It will exceed your expectations. Look no further Check-in time: 15:00 Check-out time: 11:00
Key Amenities
About this property
Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may be some ongoing construction ...
Featured review
Clean update lite filled condo close to everything All appliances work baths were clean and beds comfortable Would definitely return.
Key Amenities
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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 ...
Featured review
Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean
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 ...
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
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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, ...
Featured review
This villa had great space for our family. Room for everyone. Loved having beach towels provided—Saved on suitcase space. Pool not available due to recent hurricanes. Quiet community. Good, quick ...
Distance to beach: 0.3 miles to Crescent Beach
Key Amenities
About this property
Live steps from the sand in this beautifully renovated three-level townhouse-style condo, located in a quiet 12-unit community with deeded private beach access to Crescent Beach. This spacious, fully furnished home features 4 bedrooms and 3.5 baths, including a brand new first-floor guest suite—perfect ...
Featured review
Our stay at this Siesta Key townhouse was absolutely perfect! The location couldn’t be better — just a short stroll to shops, restaurants, and all the local conveniences. The beach rights were a fantastic ...
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
Key Amenities
About this property
*Calendar month rentals only*May-October (six-month lease) - $3900 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...
Featured review
It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...
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 ...
Featured review
The area: The general area of the condo was a fun place to visit. Plenty of stores within walking distance (just across the street). More than ample restaurants from which to choose. If you are heading ...
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 ...
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
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 ...
Featured review
Property was as described and exactly what we were looking for as a base for our week on Siesta Key and surrounding area! Beautiful condo, beach was perfect, and location was ideal for activities and restaurants. ...
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 ...
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
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 ...
Featured review
This is a beautiful condo in Bayside Club resort. A gated community. Well cared for. This condo is just 30 feet from one of the pools, tennis courts and pickle ball courts. It’s a short walk to ...
Key Amenities
About this property
Stunning Oceanfront Condo on Siesta KeyStep into your private paradise! This condo offers breathtaking ocean views from the living room, master bedroom, kitchen, and lanai. Imagine waking up to the sound of waves and ending your day with the sun dipping into the Gulf—this is coastal living at ...
Featured review
I had not realized the condo I picked was not in Siesta Keys, but that is my fault. The condo was very clean on a private beach in Turtle Beach. Very spacious and newly renovated. Everything we needed
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