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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 45 Cottages in Legacy Trail with updated reviews, rates, and availability.

The Inn On Siesta Key
The Cabana, 2 Bedroom 2 Bath (1 King, 2 Twins) | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (173)
"It was special and unique and personal. It was quaint but modern, thoughtful about guest experiences and intentional in arrangements. Teakettle and encouragement to recycle were especially refreshing! We will definitely stay here again!"
The price is AED 1,331
AED 1,641 total
includes taxes & fees
8 Apr - 9 Apr
The Inn On Siesta Key
The "Grouper"
Beach

The "Grouper"

9.4 out of 10, Exceptional, (21)
"Very clean and nice place ."
The price is AED 364
AED 775 total
includes taxes & fees
17 Apr - 18 Apr
The "Grouper"
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (52)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is AED 1,829
AED 3,134 total
includes taxes & fees
7 Apr - 8 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"The location and cleanliness was top notch. I would recomend to stay there.The description needs to be updated. It says the place has a murphy Bed. It doesn't. It has a blow up.matress.for the 3rd bed. That was a problem since i need 3 actual beds. I had 1 couple and two friends that didnt share a bed. The description made that not be a problem but it was a problem.. Other then the bed situation in the description it was very good. The description of any place is super important. That needs to...
The price is AED 779
AED 2,139 total
includes taxes & fees
27 Apr - 28 Apr
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Sun loungers, beach towels

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

10.0 out of 10, Exceptional, (1)
"This was perfect for our family. It was a quick walk to the beach. We loved it!"
The price is AED 735
AED 1,870 total
includes taxes & fees
11 Apr - 12 Apr
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (82)
"Beautiful sunsets and loved walking out to the back patio and onto the beach. Great place for 2 people. "
The price is AED 1,646
AED 2,810 total
includes taxes & fees
11 Apr - 12 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Charming cottage in quiet area, close to beach & bay.
Sun loungers, beach towels

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (265)
"This house was perfect! Close to the beach and restaurants. It had everything we needed. The fenced in backyard was great for our dog. We would definitely stay here again. "
Charming cottage in quiet area, close to beach & bay.
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal
Sun loungers

ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (15)
"The house had just been completely renovated due to the recent hurricane damage. Jim did an excellent job with everything to make sure our stay was top-notch. All the furnishings and appliances were brand new. We took the bikes out every day to Siesta Key Beach, which was just down the street. Absolutely amazing, and it took under 5 minutes! The rental location is very close (less than 1 mile) to fun restaurants in Siesta Key Village, with lot's of great bars and shopping. This place has it...
ONLY 2 WKS LEFT IN MAY 5 Min walk to Beach & Village, Private Pool,On the Canal
Across The Street From #1 Beach
Beach nearby, sun loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (320)
"Great location and very clean. Cute little cottage for a little getaway!"
Across The Street From #1 Beach
Tropical Paradise On The Beach Permit VRC17-000168
Fridge, microwave, oven, stovetop

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (127)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
The Cottage by Anna Maria Island
Beach

The Cottage by Anna Maria Island

9.6 out of 10, Exceptional, (9)
"We had a soccer tournament in Lakewood Ranch. This was a perfect location between the fields and the beach. The house was nicely decorated and suited our needs perfectly. There were even beach chairs and beach towels for our use! It was a little cool for the screened in porch but that was a very nice area. The beds were comfortable and the kitchen had all the items. The host was easy to communicate with and very responsive in answering questions. I would definitely stay here again. "
The Cottage by Anna Maria Island
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Property grounds

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (183)
"At first we didn't know what to expect. Once inside there is a cozy cottage atmosphere. Great set up for a small family. Several amenities."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Beach nearby

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Mermaid Cottage
Beach

Mermaid Cottage

10.0 out of 10, Exceptional, (11)
"We loved the two living spaces and outdoor areas. It was perfect for our varied ages. Close to food, beaches, shops,and parks."
Mermaid Cottage
Charming cottage for 2 across warm mineral springs park
Fridge, microwave, stovetop, coffee/tea maker

Charming cottage for 2 across warm mineral springs park

10.0 out of 10, Exceptional, (4)
"I stayed for 3 days to visit my aunt; this was a perfect space for me. Close to her but also to restaurants, shopping and everything I needed. Alik is great, and I'll be making sure to check in here first when I come back for more visits. Super clean, comfy and perfect for 1-2 people. Can't go wrong!! "
Charming cottage for 2 across warm mineral springs park
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Terrace/patio

Beautiful Condo on Pine Ave, 2 Blocks to Beach

9.0 out of 10, Wonderful, (21)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (71)
"This house on Anna Maria Island was a perfect vacation. The island is obviously still recovering from hurricane damage, but in a way that probably made this stay better. It was super quiet - even with construction going on - which was expected. This house has an awesome backyard with the privacy fence and pool. The pool was heated, and although cold first couple days because I'm sure they had just finished filling it for us, the last several days with it were really nice! The beach is literally...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
On the beach

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (19)
"Clean, well equipped condo with the beach for the back yard. Great location, close to Publix and local shops, restaurants and beaches, Tammy was welcoming and responsive."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
On the beach, sun loungers, beach towels

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (114)
"The rental was outstanding and in a great location. It was close to the beaches and just a short walk to many shops and restaurants. We really enjoyed having the pool. We were glad the owner took the time to check on us which is not always the case. this was a five stars plus stay!!!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.0 out of 10, Very Good, (3)
"We rented the SeaShell Cottage for the weekend of our daughter's wedding for our son, daughter - in - law and their daughter. It was only 2 blocks from the Venue - The Sandbar which was very convenient for them with an infant. The cottage was super clean and just down right adorable! We would definitely recommend and would love to return soon. "
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Legacy Trail

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4613)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is AED 684
AED 856 total
includes taxes & fees
21 Apr - 22 Apr
Tropical Beach Resorts
Anna Maria Beach Resort
On the beach, white sand, beach towels

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (193)
"This was a beautiful property...understated elegance. Very clean, well maintained with great amenities. The reception staff was wonderful and I can't wait to go back. A beautiful gem! "
The price is AED 2,163
AED 2,737 total
includes taxes & fees
7 Apr - 8 Apr
Anna Maria Beach Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2110)
"The property is a little old, but it was clean and a great location. The pool area was great as well and the laundry tubs and driers are big, you fit lots of clothes in. The front desk was very helpful and friendly. Next time we visit Sarasota we will be staying at the Hibiscus again. "
The price is AED 606
AED 684 total
includes taxes & fees
1 May - 2 May
Hibiscus Suites - Gateway to Siesta Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.