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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

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 SAR 1,559
SAR 1,902 total
includes taxes & fees
5 Apr - 6 Apr
The Inn On Siesta Key
The "Grouper"
Beach

The "Grouper"

9.4 out of 10, Exceptional, (19)
"Property was very clean and just what we needed for a quick getaway to visit friends. Property owner was quick to respond and we had check in info a couple of days before. Very close to beaches, restaurants and the island."
The price is SAR 371
SAR 791 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 SAR 1,868
SAR 3,200 total
includes taxes & fees
7 Apr - 8 Apr
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
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 SAR 750
SAR 1,909 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 SAR 1,493
SAR 2,632 total
includes taxes & fees
3 Apr - 4 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, (263)
"This cottage is just as described. New appliances and a fully equipped kitchen. Lots of towels, two king beds with excellent mattresses, and a large back yard with lounge chairs, a grill and comfy screened porch. Contact with and instructions from the hostess were outstanding. Easy walk to the beach and several excellent restaurants. "
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, (319)
"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, (182)
"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, (18)
"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
Adorable Cottage with Covered Balconies and Private Pool
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (34)
"Great property in such a cute area and just a short walk to the beach. Love the pool area and all the rooms were perfect for my friends and family."
Adorable Cottage with Covered Balconies and Private Pool
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, (4603)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is SAR 698
SAR 874 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, (191)
"We had an amazing stay on Anna Maria island. The resort has the best amenities- heated pool and jacuzzi, outdoor games, a beautiful beach and chairs and umbrellas set up. The only downfall was they were doing construction and sandwiched us in between the two rooms they were redoing which was troublesome for us and our little ones as it was very noisy. It wouldn’t keep us from returning though!"
The price is SAR 2,209
SAR 2,795 total
includes taxes & fees
3 Apr - 4 Apr
Anna Maria Beach Resort
Tiny House Siesta
Cabin (Tiny House - Yellow Lifeguard Stand) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.2 out of 10, Very Good, (242)
"The tiny house was just what we needed. Only complaint was that the air conditioner spit water when turned down. Great location super cute. Quiet at night! "
The price is SAR 345
SAR 602 total
includes taxes & fees
7 Apr - 8 Apr
Tiny House Siesta
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.