Longboat Key Vacation Rentals

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Vacation Rentals in Longboat Key

Sea Club I Beach Resort

Sea Club I Beach Resort

3 out of 5
4141 Gulf of Mexico Drive, Longboat Key, FL
This Longboat Key apartment building is on the beach, 2.8 mi (4.4 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez ...
4.5/5 Wonderful! (174 reviews)
"Clean and reasonably priced, albeit a bit outdated and in need of a few repairs. Nice pool and beach, but nothing except other resorts within walking distance (no stores, restaurants, bars, etc.)"

Reviewed on Dec 1, 2021

Sea Club I Beach Resort
Casa Del Mar Longboat Key

Casa Del Mar Longboat Key

4 out of 5
4621 Gulf of Mexico Dr, Longboat Key, FL
This Longboat Key aparthotel is on the beach, 6.4 mi (10.4 km) from Mote Marine Laboratory & Aquarium, and within 16 mi (25 km) of St. Armands Circle and John ...
4.6/5 Exceptional! (137 reviews)
"Everyone was so friendly and the private beach was great"

Reviewed on Oct 9, 2021

Casa Del Mar Longboat Key
Turtle Crawl Inn

Turtle Crawl Inn

3 out of 5
4235 Gulf Of Mexico Drive, Longboat Key, FL
The price is $400 per night from Dec 23 to Dec 23
This Longboat Key condo building is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...
4.1/5 Very Good! (74 reviews)
"Good price, next to the beach, easy parking... will come back!"

Reviewed on Jul 21, 2021

Turtle Crawl Inn
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November Dates Available!

November Dates Available!

Longboat Key, FL
The price is $149 per night from Dec 15 to Dec 15
Nestled on the beach, this Longboat Key apartment building is within 6 mi (10 km) of Cannons Marina, Lido Beach, and Beer Can Island. Sarasota BayWalk and Jewfish ...
5/5 Exceptional! (35 reviews)
Long Weekend Getaway
"Had a lovely experience. Check in was effortless, room was spotless and thoughtfully put together. Well equipped with all that is needed. Functioning kitchen, clean sheets, comfortable bed, ample space, well maintained/clean bathroom with all the towels you would need. Facilities were great. Common ..."

Reviewed on Nov 30, 2021

November Dates Available!
THE BEACH, condo #107, PRIVATE BEACH OPEN

THE BEACH, condo #107, PRIVATE BEACH OPEN

Longboat Key, FL
Situated in Longboat Key, this apartment building is within 6 mi (10 km) of Cannons Marina, Lido Beach, and St. Armands Circle. Mote Marine Laboratory & Aquarium ...
4.9/5 Exceptional! (23 reviews)
Beach getaway
"Just what we needed"

Reviewed on Aug 22, 2021

THE BEACH, condo #107, PRIVATE BEACH OPEN
Penthouse 5th floor Drop Dead gorgeous   private island & beach 100+reviews !!

Penthouse 5th floor Drop Dead gorgeous private island & beach 100+reviews !!

Longboat Key, FL
The price is $324 per night from Dec 24 to Dec 24
This family-friendly Longboat Key condo building is located on the beach, 2.7 mi (4.4 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Mote ...
4.9/5 Exceptional! (105 reviews)
Just as advertised
"We were looking for a quiet ocean front apartment and this unit did not disappoint. What you see advertised is what you get. Would definitely stay in same unit again!"

Reviewed on Dec 4, 2021

Penthouse 5th floor Drop Dead gorgeous private island & beach 100+reviews !!
Last-minute cancellation next weekend on sale

Last-minute cancellation next weekend on sale

Longboat Key, FL
The price is $293 per night from Dec 20 to Dec 20
This Longboat Key condo building is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...
5/5 Exceptional! (80 reviews)
Great stay in LBK!!
"Oceanfront, ground floor! A perfect week in Longboat Key. Amazing sunsets, cozy home and a sweet bird who visited daily! Be back soon."

Reviewed on Nov 11, 2021

Last-minute cancellation next weekend on sale
2 BR Longboat Key Gulf Front Beach Villa

2 BR Longboat Key Gulf Front Beach Villa

Longboat Key, FL
The price is $300 per night from Dec 10 to Dec 10
This Longboat Key vacation home is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...
4.7/5 Exceptional! (19 reviews)
Hidden paradise!
"Most amazing experience! Large enough for our family and even felt like we had a private pool and beach! Very clean inside and updated too! Will Definitely return!"

Reviewed on Sep 29, 2021

2 BR Longboat Key Gulf Front Beach Villa
Cabana Beach Club #5B: Suite/1 BA Resort on Longboat Key by RVA, Sleeps 4

Cabana Beach Club #5B: Suite/1 BA Resort on Longboat Key by RVA, Sleeps 4

Longboat Key, FL
Situated on the beach, this condo building is 0.3 mi (0.5 km) from Cannons Marina and within 3 mi (5 km) of Beer Can Island and Coquina Beach. Jewfish Key and ...
4.1/5 Very Good! (19 reviews)
Excellent
"Will stay again"

Reviewed on Jul 7, 2021

Cabana Beach Club #5B: Suite/1 BA Resort on Longboat Key by RVA, Sleeps 4
The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4

The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4

Longboat Key, FL
Situated on the beach, this romantic apartment building is within 6 mi (10 km) of Cannons Marina, Lido Beach, and St. Armands Circle. Mote Marine Laboratory ...
4.7/5 Exceptional! (23 reviews)
Getaway to the beach
"Nice little place right on the beach. Well stocked with what we needed for a relaxing break."

Reviewed on Oct 24, 2021

The Beach on Longboat Key #104: STUDIO / 1 BA Resort by RVA, Sleeps 4
Amazing Panoramic Gulf View and The Most Beautiful Sunset.

Amazing Panoramic Gulf View and The Most Beautiful Sunset.

Longboat Key, FL
The price is $140 per night from Jan 4 to Jan 4
Located in Longboat Key, this beachfront condo building is next to a golf course, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach ...
4.8/5 Exceptional! (72 reviews)
Nov 2021
"Beautiful property, great location. The unit was very comfortable with a great beach view. So nice to have lots of clothing storage - big dresser & huge closet. Kitchen nicely provisioned. My only recommendation would be to have a couple more dish towels & a box or two of Kleenex/tissues."

Reviewed on Nov 5, 2021

Amazing Panoramic Gulf View and The Most Beautiful Sunset.
Beach Front One Bedroom Condo Paradise. Fully Remodeled September 2021.

Beach Front One Bedroom Condo Paradise. Fully Remodeled September 2021.

Longboat Key, FL
Located in Longboat Key, this beachfront condo building is next to a golf course, 2.7 mi (4.4 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach ...
5/5 Exceptional! (2 reviews)
"Room was newly remolded, very nice and just steps away from the beach! Owners are very nice and answered all my questions!"

Reviewed on Nov 2, 2021

Beach Front One Bedroom Condo Paradise. Fully Remodeled September 2021.
NEW! Longboat Key Resort Escape: Walk to the Beach

NEW! Longboat Key Resort Escape: Walk to the Beach

Longboat Key, FL
Nestled on the beach, this Longboat Key condo building is 1.2 mi (2 km) from Cannons Marina and 2.9 mi (4.7 km) from Beer Can Island. Jewfish Key is 3.1 mi (4.9 ...
NEW! Longboat Key Resort Escape: Walk to the Beach
Welcome Snowbirds! Enjoy the beautiful Island Longboat Key with an amazing beach

Welcome Snowbirds! Enjoy the beautiful Island Longboat Key with an amazing beach

Longboat Key, FL
Situated on the waterfront, this romantic vacation home is 1.1 mi (1.8 km) from Cannons Marina and 2.8 mi (4.5 km) from Beer Can Island. Jewfish Key is 2.9 mi ...
2.8/5 (6 reviews)
The good and not so good
"On the plus side, we had a wonderful week on Longboat Key. The accommodation was well located in a safe friendly neighborhood close to Durante Park, good restaurants and a convenience store. The beach was great but definitely more than a 5 minute walk. The mini-patio on the canal was very pleasant ..."

Reviewed on May 10, 2021

Welcome Snowbirds! Enjoy the beautiful Island Longboat Key with an amazing beach
Inn on the Beach 2807

Inn on the Beach 2807

Longboat Key, FL
Situated in Longboat Key, this romantic condo building is within 2 mi (3 km) of Sarasota BayWalk, Lido Beach, and Mote Marine Laboratory & Aquarium. St. Armands ...
4.5/5 Wonderful! (4 reviews)
Beautiful Place/Views!!
"This rental was just as advertised. Very clean, beautiful views, very nicely decorated, great location and beach and has everything you need! I would definitely recommend this place!"

Reviewed on Jul 26, 2021

Inn on the Beach 2807
Beach Front Condo Paradise. Ground Floor. Studio. Fully Remodeled September 2021

Beach Front Condo Paradise. Ground Floor. Studio. Fully Remodeled September 2021

Longboat Key, FL
The price is $128 per night from Dec 12 to Dec 12
Located in Longboat Key, this beachfront apartment building is next to a golf course, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina ...
4.7/5 Exceptional! (3 reviews)
Peaceful
"Had the opportunity to celebrate my husband's birthday over Thanksgiving week in this cozy and clean studio. We slept, relaxed, and enjoyed the beach which was only walking distance for the studio. We ejoyed the sunset every day, priceless. Definately, worth coming back in summer."

Reviewed on Nov 29, 2021

Beach Front Condo Paradise. Ground Floor. Studio. Fully Remodeled September 2021
Panoramic beach View and amazing Sunset.

Panoramic beach View and amazing Sunset.

Longboat Key, FL
The price is $145 per night from Dec 15 to Dec 15
This Longboat Key condo building is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...
4.8/5 Exceptional! (50 reviews)
walk in shower
"I especially appreciated the walk in shower instead of a bath tub since I am recuperating from a broken leg. Made life easier. Office staff was quick with a replacement for a broken coffee maker. View was lovely! Only negative was a hot mattress."

Reviewed on Oct 29, 2021

Panoramic beach View and amazing Sunset.
223 STUDIO - Diplomat Beach Resort

223 STUDIO - Diplomat Beach Resort

Longboat Key, FL
Situated on the beach, this apartment building is within 6 mi (10 km) of Cannons Marina, Lido Beach, and St. Armands Circle. Mote Marine Laboratory & Aquarium ...
4/5 Very Good! (1 review)
Vacation
"Great location"

Reviewed on Mar 17, 2021

223 STUDIO - Diplomat Beach Resort
 Is this unit fabulous or what ? Direct gulffront private Island beach

Is this unit fabulous or what ? Direct gulffront private Island beach

Longboat Key, FL
This Longboat Key condo building is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...
5/5 Exceptional! (45 reviews)
The owner, Jim, was very hands on. Contacted us in middle of stay.
"A little piece of paradise."

Reviewed on Nov 24, 2021

Is this unit fabulous or what ? Direct gulffront private Island beach
NEW! Longboat Key Escape w/ Private Resort Beach!

NEW! Longboat Key Escape w/ Private Resort Beach!

Longboat Key, FL
This family-friendly Longboat Key condo building is located on the beach, within 3 mi (5 km) of Cannons Marina, Beer Can Island and Coquina Beach. Jewfish Key ...
4/5 Very Good! (4 reviews)
Easy beach access. Easy pool access.
"Literally walked out of the door and was 15’ from the pool and 40 yards from the beach."

Reviewed on Sep 13, 2021

NEW! Longboat Key Escape w/ Private Resort Beach!
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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.

Large Group Rentals Longboat Key

NEW! Sunny Gulf Coast Villa w/ Direct Beach Access

NEW! Sunny Gulf Coast Villa w/ Direct Beach Access

Longboat Key, FL
NEW! Sunny Gulf Coast Villa w/ Direct Beach Access
Only home  like this on the barrier islands

Only home like this on the barrier islands

Longboat Key, FL
Only home like this on the barrier islands
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.

Choosing the perfect Longboat Key rental

You don't have to give up the privacy of your own residence. Book a vacation rental instead of a hotel and avoid the crowds. Reserve one of Longboat Key's 10 vacation rentals now on Expedia.com.

Foodies, animal lovers, and shoppers are in for a treat, while all visitors will find something at this relaxing beach destination to delight in. Families will find plenty of fun activities in the area, including boating. Grown-ups might be interested in watching a romantic sunrise.

Dining in Longboat Key

Longboat Key is recognized for its cafés. If you'd rather eat in, that's simple too, since most vacation rentals come with full-size kitchens.

Sightseeing around Longboat Key

Some top sights around Longboat Key include University of South Florida Sarasota, Mote Marine Aquarium, and John and Mable Ringling Museum of Art. You can easily spend a leisurely day (or days) in the sunshine at Beer Can Island, Siesta Key Public Beach, or Cortez Beach. Enjoy a leisurely day of shopping at St. Armands Circle or Bay Isles Shopping Center. Unwind in the green spaces with stops at Sarasota Jungle Gardens and Marie Selby Botanical Gardens. For more things to do, spend the day at Cannons Marina or Marina Jack.

Packing for your Longboat Key trip

Whether your trip is short or long, you can use the following seasonal average temperatures to decide what to bring.

  • January–March: 64°F
  • April–June: 77°F
  • July–September: 82°F
  • October–December: 70°F

Booking your rental on Expedia

Book your vacation rental in Longboat Key easily and safely on Expedia. We can help you get in touch with the property owner to make special arrangements. With the convenience of a short-term rental, you're sure to have a memorable trip.

Frequently asked questions