Search Vacation Homes 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 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 1095 Vacation Homes in Legacy Trail with updated reviews, rates, and availability.

Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (224)
"Perfect location to walk to beach and town. The Villas and grounds were well maintained. I wouldnt hesitate staying hefe again."
Tropical Villas of Venice Beach
Anna Maria Beach Condo 1/1
Property grounds

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (168)
"This condominium was quite nice - plenty of room, clean, fully equipped kitchen, easy in-and-out, "
The price is SAR 938
SAR 1,826 total
includes taxes & fees
14 Apr - 15 Apr
Anna Maria Beach Condo 1/1
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Fridge, microwave, oven, stovetop

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

8.0 out of 10, Very Good, (67)
"Overall this worked great for us. About 2 blocks from the gulf coast. Fishing access on an inlet behind the house and pool was great for us and kids. Out of the way for major island traffic but close enough to the coast to walk and enjoy it"
The price is SAR 1,594
SAR 3,108 total
includes taxes & fees
9 Apr - 10 Apr
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Marina

New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette

10.0 out of 10, Exceptional, (4)
"The room which is privately owned is beautiful, exactly like the photos, very well appointed. The location is an older property and who ever redid this room did a great job. The check in and out process was seamless, onsight parking and restaurant/bar/pool/ work out room /boat rental was very convenient. That said, things out of this owner's control but worth noting is you are directly in a flight landing /take off pattern and the planes low and loud. Also the ice machine is right across from...
New Waterfront Unit, Sleeps 4, Heated Pool, Gym, Tiki Bar & Grill, Kitchenette
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun loungers, beach towels

SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.8 out of 10, Exceptional, (37)
"Superb location with views off back balconies of the ocean, the beach and the SUNSETS!! Well appointed kitchen with minor issues with coffee maker , garbage disposal."
The price is SAR 1,868
SAR 3,882 total
includes taxes & fees
3 Apr - 4 Apr
SIESTA KEY PRIVATE BEACH HOUSE-STEPS TO WORLD FAMOUS SIESTA KEY SAND
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite
Terrace/patio

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

9.2 out of 10, Wonderful, (49)
"our 1st VRBO experience and a resounding success! "
The price is SAR 375
SAR 626 total
includes taxes & fees
8 Apr - 9 Apr
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite
Close to Beach Access #7, Short Walk to the Village
Beach nearby, sun loungers, beach towels

Close to Beach Access #7, Short Walk to the Village

9.8 out of 10, Exceptional, (43)
"The property was very clean and the check in process was incredibly easy. Just a couple minor issues like some wall outlets not working and the shower/bathtub not draining very well. They provided us with beach towels, beach chairs and umbrellas. Close to the beach, shops and dining. Would recommend for couples and families. "
Close to Beach Access #7, Short Walk to the Village
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Beach nearby, beach towels

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

9.8 out of 10, Exceptional, (50)
"We stayed here for our annual Spring Training Boys Trip and had a great time. Was perfect for watching March Madness, poker games, KanJam, beach trips, and easy commutes to Spring Training Baseball games. The house is divided up nicely such that it basically affords for 3 different areas of the house that each have their own bathroom. Each person on the trip had their own room and shared a bathroom with one other person who was staying in the same part of the house. The house is REALLY...
The price is SAR 2,063
SAR 4,295 total
includes taxes & fees
11 Apr - 12 Apr
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Heavenly Sunset: Paradise on Anna Maria Island
On the beach

Heavenly Sunset: Paradise on Anna Maria Island

Heavenly Sunset: Paradise on Anna Maria Island
Private Oasis in Sarasota Florida
Indoor pool

Private Oasis in Sarasota Florida

10.0 out of 10, Exceptional, (26)
"My family and I came down for a weekend stay and the place was perfect for us (2 adults, 3 children ages 3, 9, 13.) We made great use of the backyard pool and lounge area. The location was great for our needs - allowed us to easily get to Siesta Key and up to Ed Smith Stadium for some O's spring training games. The house was exactly as pictured. Check in and out were very easy. "
Private Oasis in Sarasota Florida
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Smart TV, Netflix, streaming services

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

9.2 out of 10, Wonderful, (13)
"Great location! Clean, easy to find and perfect amount of room. "
The price is SAR 334
SAR 868 total
includes taxes & fees
2 May - 3 May
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Private pool House with Fountains & Beach Walkable
Beach nearby

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (170)
"Great place for our short visit for my dad’s 80th birthday! Everyone enjoyed the accommodations and the kids loved the pool. We would have loved to stay longer."
Private pool House with Fountains & Beach Walkable
Cozy Casa Azul: 12 Min to Anna Maria, Private Pool, Screened Lanai, Modern Kitchen, Family Friendly
Miscellaneous

Cozy Casa Azul: 12 Min to Anna Maria, Private Pool, Screened Lanai, Modern Kitchen, Family Friendly

2.0 star property
10.0 out of 10, Exceptional, (4)
"What a great find! House was freshly remodeled, had all the amenities we needed. The communication from the host was 1st class. If you are looking for a great vacation rental that has it all, close to town, in a nice neighborhood, this is it. Oh, one more thing which is so important to me, they have comfortable beds!!! "
Cozy Casa Azul: 12 Min to Anna Maria, Private Pool, Screened Lanai, Modern Kitchen, Family Friendly
Beachwalker Apartment: Duplex within 100 steps to the sand.
Outdoor dining

Beachwalker Apartment: Duplex within 100 steps to the sand.

9.2 out of 10, Wonderful, (24)
"Great location and great property, unit was as described, very clean and updated. Perfect location to everything the Island has to offer!"
Beachwalker Apartment: Duplex within 100 steps to the sand.
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
Terrace/patio

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

7.0 out of 10, Good, (4)
"The home was great, it had everything we needed for our stay. "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Interior

Siesta Beach Getaway - Minutes to Beach, Shops, Dining

9.6 out of 10, Exceptional, (10)
"The house was very clean and a perfect location to everything we wanted to do in Sarasota. Lots of shopping, restaurants and beaches nearby. "
Siesta Beach Getaway - Minutes to Beach, Shops, Dining
Private retreat walking distance to beautiful beaches and restaurants.
Beach nearby, sun loungers, beach towels

Private retreat walking distance to beautiful beaches and restaurants.

10.0 out of 10, Exceptional, (138)
"Quiet area, cute coffee shop close by easy parking. Tried to get ahold of owner for beeping smoke alarm and they didnt answer also kept hearing birds or something crawling on roof and dog barking other then that cute place for short stay. Clean, stocked and nicely located. "
Private retreat walking distance to beautiful beaches and restaurants.
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Outdoor pool, a heated pool

Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!

9.0 out of 10, Wonderful, (57)
"The pool was not very clean. No lights in the BBQ area and pool area. No gas for BBQ , we have to buy it. "
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13
Fridge, microwave, oven, stovetop

Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13

10.0 out of 10, Exceptional, (68)
"My wife, teenage daughter, and myself enjoyed our stay in March 2025 (4 days). The backyard was private and the pool was wonderful. We spent more time enjoying the pool than traveling to the beach--Siesta Key Beach is approximately 20 minutes away by car depending on the time of day. There are plenty of pool toys, bikes, and a well-stocked kitchen. "
Pineapples House- POOL private SOUTH facing-HOT TUB-close BEACHES- open Mar 6-13
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, (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.