10 Best Vrbo Vacation Rentals Near Crescent Beach, Siesta Key, Florida - Updated 2021

vrbo siesta key crescent beach

Sitting in the Gulf of Mexico, a short drive from Sarasota, Florida, Siesta Key is a barrier island with superb white-sand beaches and shallow, emerald waters. The small island is full of character and boasts a variety of shopping, dining options, nightlife, and beach resorts. What makes it stand out, however, are its beautiful beaches, with Crescent Beach top of the list. A region loved especially by outdoor and water sports enthusiasts Siesta Key is a fabulous place for boating, kayaking, parasailing, paddleboarding, and spotting dolphins. You can even bring your pets along and stay in one of the pet-friendly Vrbo rentals in the area. Whether you’re looking for complete relaxation in the sun, mastering new water sports, or exploring Florida’s spectacular outdoors, Siesta Key is an excellent choice. Read on to discover the best Vrbo accommodations near Crescent Beach, Siesta Key, Florida.

1. Coastal vacation rental with private beach access (from USD 319)

Imagine waking up in a comfortable king-size bed, stepping out on the balcony to watch the docked boats, enjoying the morning coffee on the patio, or starting the day on the fine-sand beach you have private access to. Sounds like a day in paradise? That’s exactly how you’ll feel staying here. To top it all off, guests also have air conditioning, a washer and dryer, cable television, Wi-Fi, a well-appointed kitchen, and access to a gym, tennis courts, and a shared pool.

Siesta Key Condo w/Private Beach Access, Wifi Included, Heated Pool, Tennis & Boat Docks
79 reviews
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
The only thing we noticed was that many of the outlets didnt seem to work
Kitchen was big and we loved sitting in the terrace
The condo had a fantastic view and we loved the private beach access Would definitely be back
We rode the trolley to downtown siesta key for dinner and walked the beach the next moring thur the access point accros the road from this condo
The condo was very clean and it provided so many things that made our stay that much better
It was updated and very clean
The condo was clean and tidy and the views of the cove were stunning
Owner was very responsive to any questions we may have had
Well when traveling to a new unfamiliar location can sometimes be difficult with directions
We had a wonderful time
well stocked and comfortable
This unit was very nice and clean and once again very detailed oriented on instructions about everything in unit and surrounding area
Not really a complaint just wanted to note
We loved the walk to the Beach
We LOVE Midnight Cove II - the location is just a quick walk to the beach and easy to hop on/off the trolly to visit the Village
but it was such a short walk across the street
The condo itself was just a SHORT SHORT walk to the Siesta Sand and
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2. Idyllic rental with private hot tub in tropical setting (from USD 160)

The most iconic feature of this vacation rental is without a doubt the charming outdoor area. Here, guests can find a lush patio with a stone path leading to the private hot tub, nestled between tropical plants. The indoors are full of character, with tropical furniture, arched ceilings, and a beach-themed kitchen. Some of the amenities available include a stereo system, free Wi-Fi, multiple televisions, air conditioning, and a washer and dryer. Guests also have access to a shared outdoor pool and a fishing pier.

“MOONMIST” Siesta Key villa with private hot tub in a 'jungle' setting
62 reviews  Wifi Available
villa 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5
Minimum Nights: 6
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Good place accessible to the beach
It has the potential to be great
(master bedroom not flushing fully)
very nice place somewhat dated and could use new pillows
It almost feels like a little oasis as you pull off the main road and into this little cluster of homes
The pool the beach and accommodations made for a delightful family holiday We would absolutely visit again
Jeannette takes pride in her villa and is responsive to any questions or concerns So go ahead
I only heard about the walkway to the bay later as we felt so insulated
Hot tub was a nice addition
etc was very accessible
Great property in a great location
This house is not a walk to the main downtown area
We recently stayed at this property and found it to be in a great location if you like the beach and being close to downtown Siesta Key
There is a pool in the middle of the development a very short walk from the house
The swimming pool in lovely also
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3. Family villa steps from the water (from USD 187)

Ideal for couples or families, this coastal-style villa is steps from the white-sand beach and turquoise waters of the Gulf of Mexico. It features two bedrooms, two bathrooms, a spacious living area, and a well-appointed kitchen. There’s free Wi-Fi throughout the property, flat-screen television, air conditioning, and covered parking. This vacation rental is part of a complex that features two beach cabanas, a game room, a large pool, and a beautiful courtyard. Restaurants, galleries, and shops are nearby.

Island House Beach Resort - Villa 35
21 reviews
villa 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
Beds were comfy with plenty of closet and drawer space
The kitchen was updated and nice
Bed pillows need replaced Awful
The kitchen was well stocked with an abundance of supplies
their own carport ala 1950's Very quiet and clean villas with updated amenities Beach and weather were perfect Getting around island with a car or eating out was a challenge due to crowds
The bungalow was clean spacious & quiet
Perfect amount of space clean and quiet
Needs towel racks in master bath
Doug answered questions in a timely matter before we arrived
beautiful Siesta Key Beach Staff was very professional polite and accommodating
The property was really nice
not even 1 blk from the beach and clean
It was great to have the ability to not have to eat out for every meal
It was spotless and in a great location
about 5 min drive to the village and a short walk to the beach
It was close to the beautiful white sandy beach
I would highly recommend this villa to anyone visiting Siesta Key Decor has a Florida-vibe which was welcomed after a day at the beach and exploring Siesta Key Village shops
Vacationed in Siesta Key during probably one of the busiest spring break weeks ever but staying at the Island House you just didn't feel the crowds Loved being able to park right outside of unit ...
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4. Remodeled coastal villa near the beach (from USD 259)

This spacious villa is full of coastal charm and modern amenities. Only steps from the beach, it is the perfect getaway for families with children. It features a newly remodeled kitchen, flat-screen television, free Wi-Fi, and a dining area for six. From the property, guests can quickly get to the private beach, the shared pool, or the clubhouse that has laundry facilities and pool and ping pong tables.

LARGE 2 BR VILLA on Siesta Key! -FALL Discount for October and November!
Siesta Key , FL, US
28 reviews
villa 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
And it felt like we had our own private beach
The property is situated directly by crescent beach
the pool heater was out
The only negative during our stay was
The children enjoyed the pool in the game room and the staff was very friendly and helpful
The villa was beautifully decorated clean and steps to the beach
Villa was very clean and well decorated Comfortable and invoked that vacation vibe
The villa was clean and very well kept and
The villa was clean and everything was in great working order
It was also very spacious
Every person associated with the property was helpful
Wonderful time had by all Staff extremely friendly and helpful
The owners and front office were helpful with any questions Highly recommended
Overall a nice vacation experience
The management was very helpful and the unit is impeccably furnished
It was located on a quiet section of Siesta Key but still near the village and local restaurants We are looking forward to returning next year
Beautiful house in a beautiful place
This villa is at the far end of the Cassablanca complex and very close to the beach
Our family had a wonderful time at this location Just steps away from the beautiful white sand beach
It really is only about 50 steps to the beach
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5. Tropical-style rental with pool and spa access (from USD 231)

Families traveling with children, and looking for a relaxing vacation should look no further. This vacation rental is part of a resort, so it offers guests access to an outdoor pool, a spa, picnic, and barbecue areas, and it is steps from the beach. Indoors, guests will find free Wi-Fi, flat-screen television, a DVD player, air conditioning, and a well-appointed kitchen with modern appliances, cookware, a coffeemaker, a toaster, and a blender.

Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large H
41 reviews  Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
No beach view or pool view
The master bed needs to be replaced
The linens and pillows need to be replaced with new better quality items
it was a comfortable unit
The pillows in particular were quite old
The condo was very clean and had everything we needed
The unit was clean and had everything that we needed
The unit itself was extremely adequate
spacious clean and well stocked
Condo is well appointed and very clean
Those two pieces of information would have been very helpful
Christina was Extremely responsive to any concerns we had
The only advice I have is we booked through Vacation Rental Pros and they didn't give us all the information that was needed
Everything was great Made wonderful memories with family
When we arrived the shower drain was clogged and the shower handle was loose -- both easily fixed but should have been noted and addressed before we arrived All this being said if the mattress w...
Loved the condo and reasonably priced
but we were also too close to the main street on the Key (I'd upgrade to a better unit in the complex next time)
Siesta Key Beach is short walk through complex Beautiful grounds
It is close to the pool and the beach not a bad walk at all
Never the less we enjoyed our time in this Condo
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6. Tropical townhouse with nearby sauna and pool (from USD 161)

This bright and spacious townhouse features charming tropical decor and lots of modern amenities, including multiple flat-screen televisions, DVD players, air conditioning, a washer and dryer, and free Wi-Fi. The recently renovated kitchen comes with a dishwasher, a coffeemaker, a microwave, a stove, an oven, a refrigerator, and a toaster. Outdoors, guests will find two patios, a waterfront picnic area with barbecue grill, a lanai, a shared pool, and tennis courts.

Tropical Townhouse at Bay Oaks - Fish from the Pier, Watch Dolphin in the Bay! Unit B62
Sarasota, FL, US
2 Bedrooms 2 Bathrooms

7. Luxury villa with outdoor pool

This family-friendly villa can comfortably sleep up to six guests between its two bedrooms and sunroom. It also features a fully equipped kitchen, flat-screen television in each bedroom and in the living room, an office area with a computer, a printer, and a copier, and two full bathrooms. The list of amenities and facilities also includes a washer and dryer, a private garage, and beach essentials – coolers, umbrellas, beach toys, fishing poles, and lounge chairs. Outdoors, guests will find two pools, two outdoor public grills, and a nearby golf course.

Luxury Villa Sleeps 6, Siesta Key Beach, Sarasota, FL - #1 Beach in the USA
58 reviews
villa 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The property provided beach loungers and chairs on the beach
The beach itself was gorgeous
Very comfortable setting for four people
We don't watch TV in the bedroom
Everything is exactly as described in the listing
Everything was nice and clean
very clean and well decorated
Owner is very accommodating and easy to work with
They even had an umbrella wagon coolers beach toys for the beach in the garage
we appreciated having all the beach/pool toys & wagon there already too
Home has everything we needed and was close to many things to see
The garage contains anything you could possibly need for an outing to the beach The owner checked into see if all our needs were met and quickly responded when we contacted him with a question
The Villa itself is in a great location if you enjoy great seafood and interesting shops plus a quick connect to neighboring Keys
Pool access is a few yards away and the beach is just a short walk
The villa location works very well - easy walk to the beach and restaurants and a short Uber ride to the village
the location right by the pool
Had a great time in Siesta Key
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8. Holiday villa steps from the white-sand beach

This spacious recently renovated villa is only steps from the beach and boasts two cozy bedrooms, two full bathrooms, a well-appointed kitchen and a living room with a dining area, recliners, flat-screen television, and a computer desk. Guests won’t know what boredom is, as the villa also features a game room with pool and ping pong tables, kids’ toys, books, and a video library. Outdoors they will find a barbecue grill, a gazebo, a patio, and a shared pool. There’s a golf course only 15 minutes away.

Sep. Holiday stil available, Large villa, 50 yds. to Siesta Beach #1
6154 Midnight Pass Road 17B
villa 2 Bedrooms 3 Bathrooms

9. Beachfront accommodation with gourmet kitchen

This stunning accommodation sits on the beach, only steps from the water. Guests will get to enjoy a luxurious interior, with a gourmet kitchen, three spacious bedrooms with flat-screen television each, two full bathrooms, and a cozy living area. Since the rental is part of a resort complex, guests also have access to the resort’s amenities, including an outdoor swimming pool, a hot tub, a tennis court, and a private clubhouse.

Siesta Key Beachfront Townhouse 3BR directly on Crescent Beach - Luxury
19 reviews
townhome 3 Bedrooms 2 Bathrooms

10. Bright and spacious villa overlooking the canal

This two-bedroom, two-bathroom villa boasts bright and cozy interiors that can accommodate up to six guests. The rental features a newly furnished living room with a sofa bed and smart television, a well-appointed kitchen, a powder room, free Wi-Fi, a washer and dryer, and air conditioning. Guests can start their days relaxing on the balcony while taking in the water views. Outside, they will find two tennis courts, several outdoor grill areas, and a gazebo. Boats are available for rental near the villa.

Midnight Cove townhouse! Private Beach with lounge chairs on beach!
33 reviews
townhome 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the private beach access with chairs/umbrellas was great
There was plenty of room for the four of us not to be on top of each other
The kitchen was spacious and well stocked with everything you need
The property itself was wonderful and the condo was AWESOME
It was great to have lounge chairs and umbrella at the beach already set up
It was very clean and comfortable
The condo was very clean and was furnished with everything we needed
The condo is absolutely gorgeous and clean very nicely decorated
the beach was absolutely awesome
and we really had no problems having vehicles stop for us
We recommend highly the resort the beach and the wonderful sun
We didn't use the pools tennis court or the clubhouse
but they also seemed well maintained
Beach is a few minutes walking distance
The unit was in a great location - an easy walk to the beautiful Siesta Key beach and area shops
This townhouse is in a perfect location for lots of fun
Townhouse was in a great location to restaurants beach and pool
Siesta Key is a wonderful vacation area and Midnight Cove is what we were looking for
Read more reviews

White sand and turquoise waters galore

Fine, white-sand beaches? Shallow turquoise waters? Luxury resorts with all sorts of amenities? Sounds pretty dreamy, right? You can find them all in our list of the best Vrbo accommodations near Crescent Beach, Siesta Key, Florida. Or if you’re looking for rentals with a private pool for a dip, Siesta Key has plenty of options for you, too. Check them out and pick the one for you.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Karina is a content creator based in Bucharest, Romania. A world traveler, obsessed over F.R.I.E.N.D.S, and a coffee addict, she dreams of one day calling Colorado home. Some of her favorite...Read more

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