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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 402 Condo Rentals in Legacy Trail with updated reviews, rates, and availability.

Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1085)
"The staff was friendly! Atmosphere was wonderful!"
The price is SAR 715
SAR 935 total
includes taxes & fees
1 May - 2 May
Captiva Beach Resort
Venice Beach Villas
Terrace/patio

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
Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave

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 SAR 636
SAR 2,401 total
includes taxes & fees
30 Apr - 1 May
Chadwick Cove Resort & Marina
Tradewinds Beach Resort
Exterior

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
Exterior

Anna Maria Sunsets - studio

9.4 out of 10, Exceptional, (218)
"Thank you, we had a great time"
The price is SAR 506
SAR 1,014 total
includes taxes & fees
30 Apr - 1 May
Anna Maria Sunsets - studio
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Microwave, oven, stovetop, dishwasher

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

8.8 out of 10, Excellent, (6)
The price is SAR 900
SAR 1,721 total
includes taxes & fees
27 Apr - 28 Apr
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Anna Maria Island - 2/1
Outdoor pool, a heated pool

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (153)
"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 SAR 600
SAR 1,392 total
includes taxes & fees
11 May - 12 May
Anna Maria Island - 2/1
Bay View Condo, Walking Distance to Beach
Property grounds

Bay View Condo, Walking Distance to Beach

9.4 out of 10, Exceptional, (36)
"The view from the condo is amazing The location is perfect We totally enjoyed sitting on the dock every evening watching the boats go by, the dolphin playing and the manatee Definitely going to stay there again!!!"
Bay View Condo, Walking Distance to Beach
Lower Pricing! Palm Bay Private Beach, 2 Heated Pools | Hot Tub | Bay Sunrises, Ready to Book!
A heated pool

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
Fridge, microwave, oven, stovetop

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (208)
"Great apartment for family getaway. Location is perfect, two wonderful pools and pleasant neighborhood"
The price is SAR 938
SAR 1,826 total
includes taxes & fees
26 May - 27 May
Anna Maria Beach Condo 1/1
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Pool

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

9.6 out of 10, Exceptional, (148)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
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
Exterior

Clean, ground floor tastefully decorated condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (78)
"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.
Outdoor dining

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

10.0 out of 10, Exceptional, (235)
"Location location location!"
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
Private kitchen

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

9.8 out of 10, Exceptional, (6)
The price is SAR 863
SAR 1,610 total
includes taxes & fees
1 May - 2 May
Charming 1-bedroom, Beachfront condo in fabulous Longboat Key steps to the beach
Dreamview Beachfront Condo - Romantic/Pet Friendly Beach Getaway
Fridge, microwave, oven, stovetop

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!!
Fridge, microwave, oven, stovetop

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
TV

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

9.2 out of 10, Wonderful, (60)
"The condo overall was ok. It is a dates unit. There were several things that didn’t work and was told they would be fixed but work was not completed during our stay. "
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
~ WE ARE OPEN! ~ BEACHFRONT ~ YES! THAT'S YOUR VIEW! ~
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (134)
"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
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (143)
"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

9.4 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
Family Suite, 2 Bedrooms (Preferred Suite) | Premium bedding, pillowtop beds, in-room safe, iron/ironing board

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4641)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is SAR 549
SAR 705 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts
Anna Maria Beach Resort
The Anna Maria Luxury Suite | View from room

Anna Maria Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (199)
"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 SAR 1,456
SAR 1,843 total
includes taxes & fees
27 Apr - 28 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, (2117)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
The price is SAR 564
SAR 638 total
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.