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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Longboat Key cottages

Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is NZ$799
includes taxes & fees
30 May - 31 May
The Inn On Siesta Key
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (123 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is NZ$977
includes taxes & fees
31 May - 1 June
Casey Key Beachfront Escape: Charming 1BR Cottage
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (66 reviews)
"Perfect location to Anna Maria Island-real “old Florida” feel."
United States
Mary W.
The price is NZ$363
includes taxes & fees
28 May - 29 May
The "Grouper"
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is NZ$417
includes taxes & fees
28 May - 29 May
Coastal Luxury 7mi to Anna Maria Private Cottage
Property grounds

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (20 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is NZ$612
includes taxes & fees
29 May - 30 May
Sunny PaG Island rental w/bikes-just steps2beach
Property grounds

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is NZ$418
includes taxes & fees
30 May - 31 May
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Exterior

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (25 reviews)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
The price is NZ$680
includes taxes & fees
16 June - 17 June
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is NZ$708
includes taxes & fees
21 June - 22 June
Lido Key Getaway - Bikes & Beach Gear
Exterior

Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.8 out of 10, Exceptional, (48 reviews)
"Yes, the Host went over the top very clean very accommodating great location!!!"
United States
Susan T.
The price is NZ$852
includes taxes & fees
9 June - 10 June
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is NZ$857
includes taxes & fees
17 June - 18 June
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is NZ$630
includes taxes & fees
9 June - 10 June
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is NZ$5,210
includes taxes & fees
4 June - 5 June
3716 7th Ave W
Property grounds

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is NZ$1,278
includes taxes & fees
1 June - 2 June
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
Nest Cottage Across street from beach and Heated Pool
Outdoor dining

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (5 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
The price is NZ$340
includes taxes & fees
3 June - 4 June
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (39 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is NZ$426
includes taxes & fees
4 June - 5 June
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Exterior

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (47 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is NZ$2,218
includes taxes & fees
14 June - 15 June
Adorable Cottage with Covered Balconies and Private Pool
Property grounds

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
Romantic Island Getaway! Just Steps from the Beach
Exterior

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"Everything was fantastic!"
United States
Kevin O.
Beautiful Guest House Near the Beach with Private Pool!
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.
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Top Longboat Key Hotel Reviews

Island Time: Open Wednesday, $199/nt + Fees!

Island Time: Open Wednesday, $199/nt + Fees!

10/10 Excellent
"I had everything I needed. It was comfortable and had a tremendous view of the Gulf. Heidi was very attentive and sent a text prior to arrival with suggestions of local things to do, as well as links to several restaurants in the area. I used that text several times! She is a very helpful and thoughtful host.I stayed over Memorial Day weekend. Usually the beaches are packed like sardines that weekend, but that was not the case. Traffic was light most of the time, and I did not have any trouble getting into a restaurant. It was quiet at night and peaceful through the day. It was a wonderfully, relaxing time, and I am definitely planning to come back."
Gordon M. 3-night trip
Posted 13 hours ago
Island Time: Open Wednesday, $199/nt + Fees!

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
939
Accommodation
23 Cottages
Lowest Price
NZ$340
Highest Price
NZ$5,210