Search Vacation Homes in Longboat Key

  • 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

Compare 142 Vacation Homes in Longboat Key with updated reviews, rates, and availability.

The Beach on Longboat Key #221S Resort by RVA
Living Room

The Beach on Longboat Key #221S Resort by RVA

9.2 out of 10, Wonderful, (35)
"Fantastic location with terrific view of the ocean. Well furnished with a well equipped kitchen. Too bad the kitchen sink garbage disposal didn’t work, there were no wardrobe closets, & the toilet in the first bedroom kept running if the handle wasn’t giggled a few times."
The Beach on Longboat Key #221S Resort by RVA
Waterfront home with private beach, a private pool, and water activities! Moku
Moku - AMI Locals

Waterfront home with private beach, a private pool, and water activities! Moku

10.0 out of 10, Exceptional, (2)
"We had a great stay! It was definitely an experience. It was a peaceful island getaway. If you are able to stay here I recommend it! Any issues we had the AMI team had a quick and efficient response-the only issues we had was our door code didn’t work for all the doors but they responded quickly and got us in in a blink of an eye, and the trash bins outside were almost full but they were out the next day to empty them so no complaints with that! Our only thing was the water in the house is VERY...
Waterfront home with private beach, a private pool, and water activities! Moku
2 BR Beach front villa with enclosed lanai overlooking the pool
Exterior

2 BR Beach front villa with enclosed lanai overlooking the pool

9.4 out of 10, Exceptional, (39)
"This was our family’s 1st stay and I can honestly say it won’t be our last!! Everything was perfect & we are so glad we found Hal’s hidden gem! Thank you for such a wonderful stay!"
2 BR Beach front villa with enclosed lanai overlooking the pool
Island Living on Longboat Key 3 minute walk to the beach!
Living area

Island Living on Longboat Key 3 minute walk to the beach!

10.0 out of 10, Exceptional, (13)
"Great location and very nice property! The host had everything we needed. Well equipped kitchen, and lots of little extras to make our stay special! Would highly recommend!"
Island Living on Longboat Key 3 minute walk to the beach!
Short walk to beach or take your boat from the canal / dock in your backyard!
Miscellaneous

Short walk to beach or take your boat from the canal / dock in your backyard!

10.0 out of 10, Exceptional, (6)
"Perfect place for me and my family. I brought my boat down and fished almost every day. Even shared fish with the neighbors across the street. Great people on either side. Beds were comfy, grill worked great. Highly recommend."
Short walk to beach or take your boat from the canal / dock in your backyard!
Piece of Paradise
Terrace/patio

Piece of Paradise

10.0 out of 10, Exceptional, (7)
"We loved our stay in Longboat for a week! The host was very attentive and responsive and the location was perfect for everywhere we wanted to go! Would come back! :) "
Piece of Paradise
Lyons Lane: Home on Longboat Key by RVA
Living room

Lyons Lane: Home on Longboat Key by RVA

9.0 out of 10, Wonderful, (2)
Lyons Lane: Home on Longboat Key by RVA
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Walking on the Sandbar

Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets

9.8 out of 10, Exceptional, (68)
"The house is full of charm; very clean and wonderfully equipped. Our kids had the best time fishing and playing in the water."
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Beach Cottage with a Private Hot Tub
Beach

Beach Cottage with a Private Hot Tub

10.0 out of 10, Exceptional, (61)
"This was a very clean property, everything you needed was in apartment. The location was beautiful, easy walk to the beach, quiet area. We absolutely loved our vacation, the owners had excellent communication and easy check in. I highly recommend this rental !"
Beach Cottage with a Private Hot Tub
Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5
Living area

Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5

10.0 out of 10, Exceptional, (17)
"This property was beautifully furnished with seashore motive. It was very clean, good lighting inside. In fact we loved it so, we kept wishing for a rainy so we could guiltlessly enjoy being inside. Relaxing in the pool after a day at the beach shelling is an extra plus. Ourhost was very responsive to our questions."
Cedars East #526 Beautiful 2 bed 2 1/2 bath town home on Longboat Key. Sleeps 5
Cedars East #507 Townhouse by RVA

Cedars East #507 Townhouse by RVA

10.0 out of 10, Exceptional, (1)
Cedars East #507 Townhouse by RVA
Silver Sands #243A Resort by RVA
Bedroom

Silver Sands #243A Resort by RVA

8.8 out of 10, Excellent, (47)
"Enjoyed it so much we will be coming back next month"
Silver Sands #243A Resort by RVA
Beautiful Beach Longboat Key Townhouse
Aerial view

Beautiful Beach Longboat Key Townhouse

10.0 out of 10, Exceptional, (14)
"Such a wonderful place! We had one of the best family stays ever. Viktor’s place was absolutely perfect for us (a family with two teenagers). We felt as we were at home. Not only was it extraordinarily equipped, but it was also comfortable, spacious, bright, and in an incredibly beautiful area. The beach is dreamy and 5 min walk. If we could, we would give you 6 stars! Thank you so much for making our stay unforgettable! Love from Argentina!"
Beautiful Beach Longboat Key Townhouse
Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach
Exterior

Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach

Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
Exterior

Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

10.0 out of 10, Exceptional, (7)
"Fabulous back area!"
Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
Starfish Bungalow A. Steps to the beach 2/1 Coastal paradise ! Large airy open layout, grill, wifi !

Starfish Bungalow A. Steps to the beach 2/1 Coastal paradise ! Large airy open layout, grill, wifi !

8.0 out of 10, Very Good, (2)
"Thanks for nice time Great location and right price."
Starfish Bungalow A. Steps to the beach 2/1 Coastal paradise ! Large airy open layout, grill, wifi !
Luxury Home with Private Beach Access and Heated Pool!
Casa Azul Beach Compound by AMI Locals

Luxury Home with Private Beach Access and Heated Pool!

9.8 out of 10, Exceptional, (8)
"The home was lovely & had everything we needed for the week. Pool area was beautiful & secluded. We enjoyed the short walk to the beach each day. The nature preserve was a delightful place to walk our dog each morning. We enjoyed our stay very much. "
Luxury Home with Private Beach Access and Heated Pool!
Private townhome steps from the beach and right next to the pool
Private kitchen

Private townhome steps from the beach and right next to the pool

10.0 out of 10, Exceptional, (8)
"We really enjoyed our stay at this super cute and well appointed condo! The decor is precious (I have several of their items in my own home!) and the proximity to the pool is unbeatable. Everything you could need is there, and the owner was available at all times to answers questions/help with anything needed. Don’t hesitate, bring your clothes and sunscreen and have fun."
Private townhome steps from the beach and right next to the pool
4 bedroom house with pool available 7th-14th June in Longboat Key. Sleeps 12
Beach

4 bedroom house with pool available 7th-14th June in Longboat Key. Sleeps 12

4 bedroom house with pool available 7th-14th June in Longboat Key. Sleeps 12
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH!
step out the back door onto your own private beach

LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH!

9.6 out of 10, Exceptional, (65)
"The location was great! The view awesome. The porch, even though the furniture was different than the picture, was perfect for sunsets. There are only two full baths and a half bath. The master bath was redone but the other two very dated with low counters but handicap accessible. Mattresses were very average. WiFi a challenge. There were only certain spots outside that you could use your cell phone. We had issues with the A/C. Furnishings below average.Overall the house is tired and needs some...
LUXURIOUS BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH!
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 Longboat Key
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 Longboat Key

Sea Club I Beach Resort
Beach

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (298)
"Great property! Great front desk people! Beautiful beach!"
Sea Club I Beach Resort
Breathtaking Beach Front Property Ground Floor Condo
Gulf of Mexico on Longboat Key

Breathtaking Beach Front Property Ground Floor Condo

9.6 out of 10, Exceptional, (128)
"Upscale, very well kept condo with all the necessary items for a pleasant vacation. Quality towels and linen. Very clean and tastefully decorated. No clutter. Highly recommend."
Breathtaking Beach Front Property Ground Floor Condo
Waterfront home with private beach, a private pool, and water activities! Moku
Moku - AMI Locals

Waterfront home with private beach, a private pool, and water activities! Moku

10.0 out of 10, Exceptional, (2)
"We had a great stay! It was definitely an experience. It was a peaceful island getaway. If you are able to stay here I recommend it! Any issues we had the AMI team had a quick and efficient response-the only issues we had was our door code didn’t work for all the doors but they responded quickly and got us in in a blink of an eye, and the trash bins outside were almost full but they were out the next day to empty them so no complaints with that! Our only thing was the water in the house is VERY...
Waterfront home with private beach, a private pool, and water activities! Moku
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.