Longboat Key Vacation Rentals from ￥48,667: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Longboat Key has to offer?

Siesta Key Island Rentals : This vacation home rental near Longboat Key comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

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Our top choices for Longboat Key vacation rentals

A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

1. Pelican Post at Anna Maria Island Inn

Bradenton Beach

Wilson

￥29,710 total

includes taxes & fees

Sep 22 - Sep 23

A two-story building with a balcony, palm trees, and outdoor seating.

2. Bridgewalk Resort

Bridge Street

Hannah

￥52,012 total

includes taxes & fees

Sep 9 - Sep 10

A water slide in a pool area with a rocky backdrop and a small waterfall.

3. Cedar Run Resort - Roam Hospitality

South Bradenton

Deliondra

￥68,173 total

includes taxes & fees

Aug 30 - Aug 31

A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

4. Haley's at The Anna Maria Island Inn

Holmes Beach

Ivet

￥32,676 total

includes taxes & fees

Aug 31 - Sep 1

An outdoor patio with a grill, white chairs, and a red umbrella.

5. Hibiscus Suites - Gateway to Siesta Key

Sarasota

Kat

￥20,624 total

includes taxes & fees

Sep 1 - Sep 2

A modern outdoor seating area with two blue chairs and a large potted plant.

6. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Bradenton

Rob

￥53,511 total

includes taxes & fees

Aug 31 - Sep 1

A pool area with a waterfall feature, lounge chairs, and palm trees.

7. Tropical Beach Resorts

South Village

Margaret Lai Ling

￥26,048 total

includes taxes & fees

Aug 31 - Sep 1

8. Gulf to Bay Island Oasis

Bradenton Beach

￥93,472 total

includes taxes & fees

Sep 8 - Sep 9

9. DOLPHIN PRIVATE HOUSE

Siesta Key Village

￥63,707 total

includes taxes & fees

Sep 1 - Sep 2

A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

10. SeaSpray Resort

Siesta Key

Isabel

￥37,093 total

includes taxes & fees

Sep 2 - Sep 3

A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

11. Seabreeze at Anna Maria Island Inn

Bradenton Beach

Rixie

￥39,256 total

includes taxes & fees

Sep 2 - Sep 3

A compact living space with a kitchen, a dining area, and a sofa with cushions.

12. Tiny House Siesta

Sarasota

Mario

￥36,522 total

includes taxes & fees

Sep 11 - Sep 12

A modern kitchen with white cabinetry, a central island, pendant lighting, and a dining area with a white sofa and table.

13. 3716 7th Ave W

Bradenton

￥491,445 total

includes taxes & fees

Sep 10 - Sep 11

14. Sun Outdoors Sarasota

Fordville

￥79,008 total

includes taxes & fees

Sep 28 - Sep 29

A beach scene with waves gently lapping at the shore and the sun setting in the distance.

15. Palm Tree Villas

Holmes Beach

Allison

￥105,302 total

includes taxes & fees

Sep 6 - Sep 7

A modern kitchen with a stainless steel refrigerator, granite countertops, wooden cabinets, and two bar stools.

16. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Sarasota

￥45,719 total

includes taxes & fees

Aug 31 - Sep 1

An outdoor deck with tables and chairs, a striped umbrella, and a view of the beach.

17. Alamanda Villas

Holmes Beach

Josephine

￥74,873 total

includes taxes & fees

Sep 28 - Sep 29

18. Pineapple Paradise 1 13 min to Beach Fire Pit

Central Sarasota

￥60,862 total

includes taxes & fees

Sep 1 - Sep 2

A covered outdoor bar area with seating, a pool, and a view of the outdoors.

19. Beach House Suites by the Don CeSar

Belle Vista

Michael

￥37,783 total

includes taxes & fees

Aug 30 - Aug 31

An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

20. Lulu's Key House Green 1/1 Upstairs

Siesta Key Village

￥79,198 total

includes taxes & fees

Aug 30 - Aug 31

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Top Longboat Key Hotel Reviews

Zota Beach Resort

8/10 Good

"Clean room, very spacious. The beach is outstanding. They charge for beach umbrellas ($30). Restaurant is a no go."

Breathtaking Beach Front Property Ground Floor Condo

10/10 Excellent

"Rooms were clean, spacious, and well appointed. Lots of beach/pool toys were available for our kids to use during the stay. These are what are leftover from others that have stayed so YMMV. The beach is close to any room. Pool was clean and has a deep end that my kids enjoyed diving into. My only gripe was the towel rule. They only provide one set of towels and linens for the stay. If something gets soiled you must launder them yourself or pay a fee for fresh."

Sea Club I Beach Resort

10/10 Excellent

"Everything was great. My only suggestion is the villa needs a "community closet" for items to be left. For instance: we flew in on a Thursday. We were hoping there would be sand toys, etc there to use for our stay since we couldn't bring them with us. Since there wasn't I went and bought sand toys, sifters, a boogie board and a skim board for my teen girls to play with while we stayed. We couldn't fly back with them without paying enormous checked bag fees so we opted to leave them "for the next family to enjoy". I imagine the cleaning crew probably had to trash them however. I wish there was a "community closet" to donate such items to for the next family and that we could have borrowed from for our stay. Otherwise it's a fantastic place to stay. We were in villa #31 and it was very well stocked and comfortable and we would love to come back and stay again. The best part, they provide loungers and chairs to take to the beach to use at your leisure! How great is that!?!"

Exclusive Beach-Style Condo with great Gulf-View 🌅 Sand Cay 206, Longboat Key

10/10 Excellent

"A great place. Awesome view of the beach. Spacious unit. Very responsive hosts. The staff at the property are very helpful and follow through. Would definitely come back."

Find out more about Longboat Key

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Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Longboat Key has to offer?

Siesta Key Island Rentals: This vacation home rental near Longboat Key comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Longboat Key?

Choose from 21 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Longboat Key Beaches and Jewfish Key are a couple of lovely local spots to get outside and enjoy nature. Siesta Key Beach and Lido Beach are other popular places to visit in the area.

What are vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

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Check prices for these dates

Our top choices for Longboat Key vacation rentals

1. Pelican Post at Anna Maria Island Inn

2. Bridgewalk Resort

3. Cedar Run Resort - Roam Hospitality

4. Haley's at The Anna Maria Island Inn

5. Hibiscus Suites - Gateway to Siesta Key

6. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

7. Tropical Beach Resorts

8. Gulf to Bay Island Oasis

9. DOLPHIN PRIVATE HOUSE

10. SeaSpray Resort

11. Seabreeze at Anna Maria Island Inn

12. Tiny House Siesta

13. 3716 7th Ave W

14. Sun Outdoors Sarasota

15. Palm Tree Villas

16. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

17. Alamanda Villas

18. Pineapple Paradise 1 13 min to Beach Fire Pit

19. Beach House Suites by the Don CeSar

20. Lulu's Key House Green 1/1 Upstairs

Find vacation rentals that suit your style

Top Longboat Key Hotel Reviews

Zota Beach Resort

The Beach on Longboat Key #227 Resort by RVA

Breathtaking Beach Front Property Ground Floor Condo

Oceanfront Oasis – Longboat Key 226 by RVA

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Island Time!

Sea Club I Beach Resort

Exclusive Beach-Style Condo with great Gulf-View 🌅 Sand Cay 206, Longboat Key

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Find out more about Longboat Key

Frequently asked questions

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