Search Villas in Legacy Trail

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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 48 Villas in Legacy Trail with updated reviews, rates, and availability.

Vacay in luxury! So close to the beach!
Beach nearby

Vacay in luxury! So close to the beach!

9.6 out of 10, Exceptional, (55)
"I loved my stay here! They had everything I needed and was clean inside and out. It was a short walk to the beach, Publix, and a strip of shops/restaurants. I would definitely recommend this place to anyone. Felt completely safe staying during my solo vacation!"
The price is AED 859
AED 2,173 total
includes taxes & fees
16 Apr - 17 Apr
Vacay in luxury! So close to the beach!
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill
Interior

Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill

9.8 out of 10, Exceptional, (127)
"Our 3rd stay at Anna Maria. LOvED the location. 5 minute walk to a very quiet beach. Close to trolley stops. Unit very clean and quiet. The shared pool was no issue. Had a family of 5 next door one week. A retired couple the 2nd week. With the beach so close and other things to do in the area, we were rarely at the pool at the same time. Only thing I can suggest is clear out some of the unneeded stuff in the BR closets and the king bed is rather firm and ‘creaky’. But we adjusted just fine....
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill
Now Booking for Summer! Sea Site Retreat Unit A! Great amenities nearby! Short walk to the beach!
Fridge, microwave, oven, stovetop

Now Booking for Summer! Sea Site Retreat Unit A! Great amenities nearby! Short walk to the beach!

9.6 out of 10, Exceptional, (20)
"We had an amazing stay! The house and location were great. We had a couple of hiccups the first day. The WiFi and the AC wasn’t working. When I called the property manager jumped on it and it was addressed the next day. Luckily it was cool enough to open windows for the evening. Plenty of space for our family of 4 with room to spare. We throughly enjoyed the balcony and being a few steps from the beach. Place was overall clean, only issue we had was we found carpet staples everywhere but I...
Now Booking for Summer! Sea Site Retreat Unit A! Great amenities nearby! Short walk to the beach!
⚓Now Booking for Summer! Sea Site Retreat Unit B! Short walk to the beach!⚓
Terrace/patio

⚓Now Booking for Summer! Sea Site Retreat Unit B! Short walk to the beach!⚓

9.2 out of 10, Wonderful, (30)
"It was fine for our work trip but the property could use a little TLC. Plenty of space overall, huge master bedroom. Overall the property is kind of plain, nothing bad, just not exciting."
⚓Now Booking for Summer! Sea Site Retreat Unit B! Short walk to the beach!⚓
Palma Sola Villa with Private Spa Pool & Sunset Cruises 🚤
Property grounds

Palma Sola Villa with Private Spa Pool & Sunset Cruises 🚤

10.0 out of 10, Exceptional, (47)
"This gem of a property is in a very quit neighborhood. This home is kept immaculate and is a perfect place to stay if you're looking to be close to the best beaches in the area. The owner, Mike, always responded back quickly if I had a question. Excellent 10/10"
Palma Sola Villa with Private Spa Pool & Sunset Cruises 🚤
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Lake

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

9.8 out of 10, Exceptional, (105)
"We had the greatest little getaway here! The place was clean and stocked with everything we needed, including beach supplies. It was awesome to walk directly onto the beach :) We can’t wait to come back! "
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Waterfront Villa Seaglass
A heated pool

Waterfront Villa Seaglass

9.8 out of 10, Exceptional, (78)
"20 minutes from the braves and plenty of fish to catch off the dock! Thoroughly enjoyed it!!"
Waterfront Villa Seaglass
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
Beach nearby, sun loungers, beach towels

MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street

10.0 out of 10, Exceptional, (113)
"Clean, comfortable, well-stocked home within walking distance to the beach, restaurants, bars, and shopping. Would definately stay again!"
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Beach nearby

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

9.6 out of 10, Exceptional, (90)
"The property is just as described! It was incredible. The beach and stores were all walking distance. Definitely would stay there again."
The price is AED 1,623
AED 3,684 total
includes taxes & fees
9 Apr - 10 Apr
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Beach nearby, sun loungers, beach towels

Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

9.8 out of 10, Exceptional, (93)
"Totally as advertised. Short distance from a wonderful beach and all of the stuff you would need - wagon, chairs, towels etc. The cottage is very nice. Comfy bed and plenty of towels with a hot shower. We loved being walking distance to the old village shopping area for groceries and restaurants and entertainment. We hardly moved our car the whole week. Would rent again. "
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
AMI Moana Villa 3-minute walk to the beach plus community heated pool
Beach nearby, sun loungers, beach towels

AMI Moana Villa 3-minute walk to the beach plus community heated pool

9.4 out of 10, Exceptional, (18)
"We loved staying here. Quiet, comfortable and clean. Would definitely recommend it."
AMI Moana Villa 3-minute walk to the beach plus community heated pool
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.0 out of 10, Very Good, (74)
"Most properties are still in bad shape from hurricanes. Paradise cove in lemon bay looks great , no signs of damage. Owner was great and seen him out doing improvements daily. Pool coming soon. Highly recommend Paradise Cove if you’re truly looking to relax in peace and comfort. Everything you need is also here as far as laundry room and stores that you can walk to. Also private beach and fishing which my dog and I used daily. Thanks Paradise Cove "
Paradise Cove at Lemon Bay
Sunswept Villa 4 - riverwalk & park front w/ pool, near beaches - pet friendly!
Sun loungers, beach towels

Sunswept Villa 4 - riverwalk & park front w/ pool, near beaches - pet friendly!

10.0 out of 10, Exceptional, (23)
"It was a great experience. Hosts were awesome. Property clean and well kept. Definitely would recommend to others "
Sunswept Villa 4 - riverwalk & park front w/ pool, near beaches - pet friendly!
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
Beach nearby, sun loungers, beach towels

Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level

10.0 out of 10, Exceptional, (91)
"Property was wonderful, loved the outside pool! Communication was incredible, every time I called she answered! Would totally recommend staying at this VRBO."
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
Venice Island / Venice Beach Luxury Villa
Beach

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (114)
"Would love to come back"
Venice Island / Venice Beach Luxury Villa
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
Beach nearby, sun loungers, beach towels

Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!

10.0 out of 10, Exceptional, (112)
"Nice and quiet stay on Anna Maria island. Very clean place and great location. Simple accommodations but worked for us well. "
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
6 BR Heated Pool, Mins from IMG and Anna Maria
Dining

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
The price is AED 806
AED 2,611 total
includes taxes & fees
6 Apr - 7 Apr
6 BR Heated Pool, Mins from IMG and Anna Maria
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Beach nearby, sun loungers, beach towels

Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!

10.0 out of 10, Exceptional, (12)
"We stayed in this rental for the month of Jan 2025. It was very comfortable and well equipped. We particularly enjoyed the large grill in the patio for cooking. The best feature was the convenient location - 12 minutes to Siesta Key Beach or downtown Sarasota, 15 minutes to St. Armands and Lido Beach, walking distance to grocery and drug stores, a few restaurants, and Barnes and Nobles. Our host Mark was very responsive and available for anything we needed throughout our visit. A very...
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Waterview Vacation Retreat Close To Ocean
Interior

Waterview Vacation Retreat Close To Ocean

10.0 out of 10, Exceptional, (5)
"We've stayed in another property nearby owned by this host. This was another great stay. Beautiful home with lots of space and light. Love the fire pit out back at night. Easy driving to Spring Training games we were in town to see. Will definitely stay again. The host answers all communication quickly and the house is very clean and well appointed. "
The price is AED 680
AED 1,536 total
includes taxes & fees
4 Apr - 5 Apr
Waterview Vacation Retreat Close To Ocean
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
Beach nearby, sun loungers, beach towels

Ideal Location, Stunning Villa! Close to beach, beach gear provided!

9.8 out of 10, Exceptional, (113)
"We had a snafu with checking in - incorrect door code given- but it was quickly resolved and the rest of the stay was flawless. This property is a gem - brand new finishes and a block and a half away from the beach makes it the perfect place to stay. Very well appointed for all of your needs. Thank you for a great vacation!"
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
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.
Don't see what you're looking for?
See all available properties in Legacy Trail
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Legacy Trail

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4609)
"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, (192)
"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 2,249
AED 2,847 total
includes taxes & fees
10 Apr - 11 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, (248)
"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 AED 338
AED 589 total
includes taxes & fees
10 Apr - 11 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.