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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 414 Condo Rentals in Legacy Trail with updated reviews, rates, and availability.

Captiva Beach Resort
Florida Family Single | Private kitchen | Fridge, microwave, coffee/tea maker, toaster

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1090)
"Close to beach and pool ."
The price is AED 659
AED 869 total
includes taxes & fees
12 May - 13 May
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (406)
"Clean, spacious unit, great amenities "
Venice Beach Villas
Chadwick Cove Resort & Marina
Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (6)
"Very nice and updated property with a great panoramic view of the bay and ocean. Easy check in and checkout. Close to everything in Montasota Key/Englewood. "
The price is AED 552
AED 2,271 total
includes taxes & fees
27 May - 28 May
Chadwick Cove Resort & Marina
Tradewinds Beach Resort
Private beach nearby, sun loungers, beach towels

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (375)
"Staff was friendly and welcoming. Location was amazing. Pool was very nice. Very pleasant stay. Will be back!"
Tradewinds Beach Resort
Anna Maria Sunsets - studio
Sun loungers, beach towels

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (220)
"Compact but functional and comfortable. Great for a getaway to get you "beach fix.""
The price is AED 551
AED 1,084 total
includes taxes & fees
14 May - 15 May
Anna Maria Sunsets - studio
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
On the beach

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

9.0 out of 10, Wonderful, (8)
"Very nice beachfront and pool is nice as well"
The price is AED 882
AED 1,706 total
includes taxes & fees
30 May - 31 May
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Anna Maria Island - 2/1
Property grounds

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (156)
"Perfect place to spend a lovely weekend on AMI. The condo was the right size, clean, fully stocked, and we were able to walk everywhere. "
The price is AED 441
AED 1,178 total
includes taxes & fees
18 May - 19 May
Anna Maria Island - 2/1
Bay View Condo, Walking Distance to Beach
Beach nearby

Bay View Condo, Walking Distance to Beach

9.4 out of 10, Exceptional, (36)
"We enjoy the main level condo with a nice view of the water. The dock is great for fishing. "
Bay View Condo, Walking Distance to Beach
Sun, Sand and Savings Sarasota Deals Up to 15% Off
A heated pool

Sun, Sand and Savings Sarasota Deals Up to 15% Off

9.4 out of 10, Exceptional, (94)
"Excellent location. Great weather. We especially enjoyed the hot tub and beach."
Sun, Sand and Savings Sarasota Deals Up to 15% Off
Anna Maria Beach Condo 1/1
Beach

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (212)
"Great location, very clean and well equipped. Host was great to communicate with. Highly recommended, and would definitely stay again."
The price is AED 826
AED 1,669 total
includes taxes & fees
21 May - 22 May
Anna Maria Beach Condo 1/1
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
On the beach, sun loungers

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (150)
"Excellent location right on the beach! Quiet and relaxing. The property provides beach loungers and you can bring your own umbrella or rent one for the day or your stay. Our unit was on the 2nd floor and liked that there were 2 Queen Beds in the one bedroom. Furnishings were a little worn around the edges, but was comfortable and had all we needed for cooking and even a cooler for the beach, "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Beach nearby, sun loungers, beach towels

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (80)
"Had a great trip! Clean, quiet & great location!"
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
Outdoor dining

Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.

10.0 out of 10, Exceptional, (238)
"Condo was very clean, conveniently located, and would definitely stay here again."
Sea Pirate Cottage By The Sea on Anna Maria Island, Smart TV in every room.
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
On the beach

Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

9.8 out of 10, Exceptional, (7)
The price is AED 845
AED 1,542 total
includes taxes & fees
12 May - 13 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
On the beach

Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

9.6 out of 10, Exceptional, (55)
"Will stay again!"
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
Welcome to Siesta Dreams at Casa Mar!!
On the beach

Welcome to Siesta Dreams at Casa Mar!!

9.6 out of 10, Exceptional, (50)
"we had a great time at this cute little condo.we liked that the beach was just a short walk away. everything was great!"
Welcome to Siesta Dreams at Casa Mar!!
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
Beach nearby, sun loungers, beach towels

Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key

9.2 out of 10, Wonderful, (61)
"This was a good condo style property on the key. Good location. Great owner with great communication. I did not have the opportunity to ask about the water heater regarding showers. The shower would get luke warm, but we did get ready at the same time. I would definitely rent this property again. "
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
~ WE ARE OPEN! ~ BEACHFRONT ~ YES! THAT'S YOUR VIEW! ~
On the beach, sun loungers, beach towels

~ WE ARE OPEN! ~ BEACHFRONT ~ YES! THAT'S YOUR VIEW! ~

10.0 out of 10, Exceptional, (135)
"We loved everything about this condo. Will definately be back"
~ WE ARE OPEN! ~ BEACHFRONT ~ YES! THAT'S YOUR VIEW! ~
See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool
Beach nearby, sun loungers, beach umbrellas, beach towels

See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool

9.8 out of 10, Exceptional, (145)
"2nd year in a row coming down to Siesta Key for Christmas and 2nd time staying at a property managed by Gail and H. They are attentive and thoughtful hosts and their properties are immaculate and exactly as advertised. We’re already booked to return in November!!"
See July 4 Fireworks across the street on #1 Siesta Beach Spacious 2+2Condo,pool
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Outdoor pool, a heated pool

Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

9.6 out of 10, Exceptional, (17)
"The condo was beautiful, clean and well stocked. We had everything we needed for a Christmas beach vacation. "
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
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, (4648)
"Amazing trip and stay!!!"
The price is AED 492
AED 639 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts
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, (2123)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is AED 553
AED 625 total
includes taxes & fees
12 May - 13 May
Hibiscus Suites - Gateway to Siesta Key
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, (202)
"This is a very good place to have relaxed days. The room was perfect, with all that we needed. The view was perfect. All the amenities help to have fun."
The price is AED 1,946
AED 2,463 total
includes taxes & fees
12 May - 13 May
Anna Maria Beach Resort
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.