Book Direct & Save - No Service Fees
Distance to beach: 0.3 miles to Siesta Key Beach access 10
Key Amenities
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: 0.5 miles to Siesta Key Beach
Key Amenities
About this property
*Calendar month rentals only*May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, February, and March - $6900 per month plus utilities April - $4900 per month plus ...
Featured review
This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...
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 ...
Key Amenities
About this property
Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 week min. CLEANING ...
Key Amenities
About this property
COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 4TH FLOOR AND IS A 1 BEDROOM / 1 BATH CORNER UNIT. WASHER/DRYER IN UNIT. COMPLEX OFFERS POOL, TENNIS, 1 ASSIGNED COVERED PARKING SPACE. UNIT HAS 2 TV'S, DVD. HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT ...
Why Choose FloridaRentals.com?
No Booking or Service Fees
Save up to 20% compared to other websites - no hidden costs.
Connect Directly with Hosts
Book with confidence and get the best rates.
Florida's #1 Vacation Rental Site
Trusted by millions - your go-to for the perfect Florida getaway.
Distance to beach: 0.7 miles to Turtle Beach
Key Amenities
About this property
Welcome to Bayside Haven at the Pointe, your perfect getaway nestled along the serene shores of Sarasota Bay. This charming vacation rental features two spacious bedrooms and two full bathrooms, ensuring ample comfort and privacy for you and your guests.The fully equipped kitchen is perfect for preparing ...
Key Amenities
About this property
You will love the grounds with 7 acres of lush tropical landscaping. Our unit is complete with coastal décor, newer appliances and washer/dryer. Walk to Siesta Key Beach or swim in the heated pool. We have several grills, a clubhouse with library, and a peaceful lagoon. Siesta Key Village is filled ...
Distance to beach: 0.5 miles to Siesta Key Main Beach
Key Amenities
About this property
Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...
Featured review
Thank you Barbara and Angelo for providing a beautiful "home away from home" for our spring vacation. We have rented on Siesta Key several times and this was definitely our favorite location. Your renovations ...
Key Amenities
About this property
Quaint 1 bedroom bungalow with Murphy Bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, french doors opening to a private brick patio. 2 Smart TV's. 43 inch in living room and 32 inch in bedroom. Kitchen offers a mini convection oven ...
Key Amenities
About this property
Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...
Key Amenities
About this property
2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...
Key Amenities
About this property
COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 3RD FLOOR AND IS A 2 BEDROOM / 2 BATH UNIT. COMPLEX OFFERS HEATED POOL, TENNIS, FULL LAUNDRY FACILITY AT COMPLEX, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS WOOD FLOORS THROUGHOUT , LEATHER FURNISHINGS AND ...
Key Amenities
About this property
2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...
Key Amenities
About this property
Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks Community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits ...
Key Amenities
About this property
COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 2ND FLOOR AND IS A 2 BEDROOM / 2 BATH REMODELED UNIT. COMPLEX OFFERS A NEWLY RENOVATED POOL AND POOL DECK, TENNIS, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS TILE IN THE MAIN TRAFFIC AREAS WITH CARPET IN ...
Distance to beach: 0.1 miles to Crescent Beach on Siesta Key
Key Amenities
About this property
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 ...
Distance to beach: 0.5 miles to Siesta Key Main Beach
Key Amenities
About this property
Sweet Siesta Key Condo walking distance to #1 Beach in America! Spacious and Quiet One Bedroom with King Bed, Screened Lanai, Wireless Internet, Flat screen TV’s, full kitchen with amazing water filtration system. Easy Walk right over to Siesta Key Main Beach, and their 6 new lighted Pickleball ...
Featured review
Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...
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. ...
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.
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: 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 ...
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 ...
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 ...
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
Harbor Towers 2nd floor unit located a few blocks south of the Siesta Public beach. Beautiful property located on the intercoastal. Pool and tennis, propane grills and coin laundry on each floor and elevator. NO smoking in unit and NO pets. Units sleeps 4, 1 King and 2 twins. 2 Week min. CLEANING FEE ...
Key Amenities
About this property
Renovated 1/1 condo with everything you need to relax or work from home! Bedroom offers a king size bed, large closet, dresser, two nightstands with storage, desk equipped with keyboard, mouse, printer and laptop stand, and large TV with WiFi connection to watch all your favorite apps. There’s also ...
Featured review
We really enjoyed your beautiful condo and we’re so comfortable there and had a great time. We loved the beach-themed decorating so much And the king sized bed was so cold for table that we want to buy ...
Key Amenities
About this property
This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...
Featured review
The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...
Key Amenities
About this property
Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.*** It seems like a miracle that Midnight Cove II again was extremely ...
Featured review
We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.
Key Amenities
About this property
Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...
Key Amenities
About this property
2ND FLOOR UNIT, COMPLEX OFFERS, POOL, WIFI AT THE POOL AREA ONLY. ( SIESTA 4 RENT DOES NOT OFFER TECH SUPPORT), NEAR SHOPPING, 2 BLOCKS TO THE PUBLIC BEACH ACCESS, END UNIT OFFERS A LITTLE MORE SPACE. 2 WEEK MIN. LAUNDRY FACILITY ON 1ST FLOOR. 1 King, 2Twin, 1SOFA BED. CLEANING FEE $205
Key Amenities
About this property
COME RELAX IN THIS 3RD FLOOR, FIRETHORN UNIT LOCATED IN MIDNIGHT COVE I, BAYSIDE. COMPLEX OFFERS 2 POOLS, BEACH CHAIRS PROVIDED BY ASSOCIATION, 2 TENNIS COURTS AND BEACH ACCESS THROUGH THE GULF SIDE. (NO BEACH CHAIRS OR EQUIPMENT PROVIDED) 3RD FLOOR UNIT, (NO ELEVATOR) HAS OPEN BALCONY WITH VIEW OF CANAL, ...
Key Amenities
About this property
GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...
Key Amenities
About this property
This 1 bedroom , 2nd Floor unit in Siesta Village offers, great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 2 TV's. Complex offers community pool and laundry facilities located off common ...
Featured review
We had a great vacation here! Condo was very nice, clean and well supplied. Close to Siesta Village, Beach and within walking distance of almost everything. A definite hidden treasure!
Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach
Key Amenities
About this property
*Calendar month rentals only*May-October (3-7 month lease) - $3900 per month plus utilities and tax. November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance ...
Featured review
I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors ...
Distance to beach: 0.3 miles to Siesta Key Beach
Key Amenities
About this property
*Calendar month rentals only*July- December (six-month lease) - $3900 per month plus utilities July- October (four-month lease) - $3500 per month plus utilities December - $6900 per month plus utilities January, February, and March- $9800 per month plus utilities April and May - $7900 per month ...
Featured review
Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for ...
Key Amenities
About this property
4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...
Featured review
We were due to stay for 2 weeks from 26th sep unfortunately due to hurricane helene we weren't able to stay .siesta rentals returned all our sad but we will come ahain
Distance to beach: 0.0 miles to Siesta Key Main Beach
Key Amenities
About this property
Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. King bed in bedroom and a Queen bed in living room. Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness Gym, locker rooms, Marina, ...
Featured review
what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina, ...
Distance to beach: 0.3 miles to Crescent Beach on Siesta Key
Key Amenities
About this property
Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal ...
Featured review
Absolutely loved our stay at Siesta Key. The condo is clean, well equipped with everything you need, easy access to food and the beach. Would definitely stay here again
Key Amenities
About this property
Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...
Featured review
We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for ...
Key Amenities
About this property
This is a Gem, 2nd/3rd floor Bayfront townhome, Living area on second floor and interior stairs lead to bedrooms on 3rd floor. Top of the line unit, offering travertine floors, new kitchen and baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet ...
Distance to beach: 0.3 miles to Siesta Key Beach
Key Amenities
About this property
Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable ...
Featured review
We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this ...
Distance to beach: 800 feet to Siesta Key Beach
Key Amenities
About this property
Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...
Key Amenities
About this property
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.
Distance to beach: 250 feet to Siesta Key
Key Amenities
About this property
On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...
Distance to beach: 1 miles to Crescent Beach
Key Amenities
About this property
AFTER 2 HURRICANES E91 IS READY FOR GUESTS!! We thank God that our condo was spared! E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen ...
Featured review
Arrived late at night,found the instruction's from Ana very helpful .Delighted with the layout and condition.Not a thing out of place. It was a pleasure to stay there.Would recommend this condo to everyone.
Key Amenities
About this property
Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chef's dream, ...
Distance to beach: 200 yards to Crescent Siesta Key Beach
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 ...
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 ...
Key Amenities
About this property
Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour ...
Featured review
We cannot say enough about how great our stay was, Roy was a great host and super nice guy. Very easy to work with. We loved the pool and hot tub and location of the property. We preferred this private ...
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 ...
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 ...
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.
Featured review
We enjoyed our stay at Our House at the Beach. It was in a great location. You can walk across the street to siesta key Beach. You can’t see the ocean from the Balcony however because it’s on a lower ...
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 ...
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: 200 yards to Siesta Key Crescent Beach
Key Amenities
About this property
SIESTA SUMMER SAVINGS! UP TO 20% OFF YOUR SUMMER STAY BETWEEN 5/31/25 AND 9/1/25 WHEN BOOKING DIRECTLY ONLINE Online booking: Click link in Host information section of this listing and use promo code Anchor6415 at checkoutWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', ...
Featured review
We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location ...
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!
View on map
List view