Holiday Rentals in Longboat Key
Revenue impacts this sort order. Learn more
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
931 rentals in Longboat Key.
***Bermuda-esque Island Cottage! Steps to Sand!***
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Take a Peek fabulous unit
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Breathtaking Beach Front Property Ground Floor Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beach Front One Bedroom Condo Paradise. Fully Renovated. Ground Floor.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
1 bedroom single story ocean view
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
1 bedroom single story condo near pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Gorgeous condo on the beautiful Longboat Key beach
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beautiful Updated Beachfront Condo on the Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Gulf Condo with Heated Pool - Open Thursday, Friday, $185/nt!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Unit #309 great rates, 2 Bed/2 Bath, view of ocean, steps to the sandy beach.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Direct Beachfront Gulf with Amazing Views
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Georgeous Condo Directly On The Beautiful Longboat Key!!!!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
As seen on
Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Just had cancel July 29-Aug 5 Rare 5th floor Penthouse160 + 5 star reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beach view. Year around Balcony Sunsets.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Updated Beach Style Condo at Sand Cay with Great Ocean Views.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Direct walk out 50 feet from the sand private island
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Panoramic beach View and amazing Sunset.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Incredible Panoramic Gulf View and The Most Beautiful Sunset.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Beach on Longboat Key #106: STUDIO / 1 BA Resort by RVA, Sleeps 2
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beachfront Villa on Serene Gulf of Mexico
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
2/2 GULF SIDE UPDATED APARTMENT (look for seasonal specials on select dates)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Wonderful Canal Front Condo! Bring Your Boat!UNIT 11
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Silver Sands #257A Resort by RVA
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Client texted me said View Crazy
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Silver Sands #242 Resort by RVA
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Direct Oceanview Condo on Peaceful Longboat Key!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
THE BEACH, condo #107, PRIVATE BEACH
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
LaPlaya 101E-Relax on your private lanai under the palms!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Silver Sands #255A Resort by RVA
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Beach on Longboat Key #226: STUDIO / 1 BA Resort by RVA, Sleeps 4
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beach Front Condo Paradise. Ground Floor. Fully Renovated with a full Kitchen.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Silver Sands #232 Resort by RVA
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
As seen on
Silver Sands #243A: HOTEL / 1 BA on Longboat Key by RVA, Sleeps 2
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beachfront Condo at Prestigious Long Boat Key Club
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Wonderful Bay Front Condo! See Manatees Right From Your Doorstep!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
The Beach on Longboat Key #225 Resort by RVA
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beach Castle Resort 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
LaPlaya 202E-Catch the gentle Gulf breezes on your private balcony beneath the s
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Beautiful canal front unit!See manatees playing from your living room.Cabana #12
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
One-of-a-kind home right on the gulf of Mexi
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Spacious 2Bdrm Longboat Key Condo
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
As seen on
Silver Sands #254: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
Cabana Beach Club #7 Resort by RVA
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
As seen on
Showing results 1-50 of 931
Frequently Asked Questions about Longboat Key
- Yes, here are some popular holiday rentals in Longboat Key that have a pool:
- 1 bedroom single story ocean view
- 1 bedroom single story condo near pool
- Incredible Panoramic Gulf View and The Most Beautiful Sunset.
- Yes, here are some popular holiday rentals in Longboat Key that have internet access:
- ***Bermuda-esque Island Cottage! Steps to Sand!***
- Take a Peek fabulous unit
- Breathtaking Beach Front Property Ground Floor Condo
- The best pet friendly rentals in Longboat Key are:
- Spacious 2Bdrm Longboat Key Condo
- A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.
- Beach Cottage with a Private Hot Tub
- Some of the most popular kid friendly rentals in Longboat Key are:
- Take a Peek fabulous unit
- Breathtaking Beach Front Property Ground Floor Condo
- Luxury Beach Condo with Breathtaking Views PROMO SUPER PROMO 106 August 2023