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Featured Condo Rentals in Legacy Trail

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1087)
"Close to beach and pool ."
The price is NZ$400
includes taxes & fees
4 May - 5 May
Captiva Beach Resort

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (406)
"Loved it. The owner is so friendly and he keeps the place clean and respectful. He offers a lot of amenities. "
Venice Beach Villas

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (5)
"This was an excellent property to stay in. I will definitely rebook when I travel to Englewood, Fl. "
The price is NZ$992
includes taxes & fees
12 May - 13 May
Chadwick Cove Resort & Marina

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (374)
"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

9.2 out of 10, Wonderful, (220)
"Thank you, we had a great time"
The price is NZ$468
includes taxes & fees
6 May - 7 May
Anna Maria Sunsets - studio

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

9.0 out of 10, Wonderful, (7)
"Very nice beachfront and pool is nice as well"
The price is NZ$777
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

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 NZ$596
includes taxes & fees
11 May - 12 May
Anna Maria Island - 2/1

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

Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!

9.4 out of 10, Exceptional, (94)
"Excellent space"
Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (210)
"Great apartment for family getaway. Location is perfect, two wonderful pools and pleasant neighborhood"
The price is NZ$796
includes taxes & fees
22 May - 23 May
Anna Maria Beach Condo 1/1

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

9.6 out of 10, Exceptional, (149)
"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, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (80)
"Had a great trip! Clean, quiet & great location!"
Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach

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

10.0 out of 10, Exceptional, (235)
"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

9.8 out of 10, Exceptional, (7)
The price is NZ$723
includes taxes & fees
7 May - 8 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach

Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

9.6 out of 10, Exceptional, (55)
"Great!"
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway

Welcome to Siesta Dreams at Casa Mar!!

9.8 out of 10, Exceptional, (48)
"A good stay overall."
Welcome to Siesta Dreams at Casa Mar!!

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! ~

10.0 out of 10, Exceptional, (135)
"Beautiful rental and location. HOWEVER, our host failed to mention that multiple units directly below us were undergoing major reconstruction from 8 AM for 10-12 hours daily. To disclose this in a timely manner should have been an integral component of the deal. Not happy. "
~ WE ARE OPEN! ~ BEACHFRONT ~ YES! THAT'S YOUR VIEW! ~

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

9.8 out of 10, Exceptional, (144)
"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

9.4 out of 10, Exceptional, (16)
"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

3.5 star property
9.4 out of 10, Exceptional, (4642)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is NZ$362
includes taxes & fees
18 May - 19 May
Tropical Beach Resorts

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (201)
"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 NZ$1,162
includes taxes & fees
11 May - 12 May
Anna Maria Beach Resort

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2121)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is NZ$260
includes taxes & fees
4 May - 5 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.