A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Guest Houses in Longboat Key

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Longboat Key guest houses

A marina with boats docked, a wooden dock, and a clear sky.

1. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Whitfield Estates
7.4 out of 10, Good, (6 reviews)
"Looking for a couple nights close to Anna Maria Island without being ON the island. Turns out we were here once before and didnt realize it was the same place. Love the "Back Yard" surprises"
United States
Susan B.
$184 nightly
The price is $215
Oct 8 - Oct 9
Total with taxes and fees
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
A beach with gentle waves and a sunset.

2. Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
Central Sarasota
9.8 out of 10, Exceptional, (137 reviews)
"Stephanie is a great host. The coach house is very clean and comfortable and all of the extras available to us made the trip so good - like beach chairs, umbrellas, e-bikes. It’s a great location with Main Street walkable and fantastic beaches by car."
United Kingdom
Liz
$165 nightly
The price is $184
Sep 28 - Sep 29
Total with taxes and fees
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
A covered outdoor deck with a ceiling fan, wooden railing, and a seating area with cushions.

3. Siesta key Guest House 5 star on the water Private

Siesta key Guest House 5 star on the water Private
South Sarasota
8.8 out of 10, Excellent, (21 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
$339 nightly
The price is $356
Oct 1 - Oct 2
Total with taxes and fees
Siesta key Guest House 5 star on the water Private
A lifeguard tower with a blue umbrella and a yellow flag on a sandy beach.

4. Close to Siesta Key beach with a hot tub and a large garden

Close to Siesta Key beach with a hot tub and a large garden
Sarasota
9.8 out of 10, Exceptional, (140 reviews)
"Wonderful place to stay! Spacious, near Siesta Key beaches, and great pizza walking distance "
United States
Kari H.
$238 nightly
The price is $265
Oct 8 - Oct 9
Total with taxes and fees
Close to Siesta Key beach with a hot tub and a large garden
An aerial view of a coastal town with a long sandy beach, a marina, and residential buildings.

5. Charming Cottage in Pass-A-Grille Beach, Dogs Ok

Charming Cottage in Pass-A-Grille Beach, Dogs Ok
Pass-a-Grille
9.6 out of 10, Exceptional, (44 reviews)
"Perfect place for a getaway"
United States
Barbara F.
$286 nightly
The price is $319
Sep 25 - Sep 26
Total with taxes and fees
Charming Cottage in Pass-A-Grille Beach, Dogs Ok
An aerial view of a coastal town with a long sandy beach, a marina, and residential buildings.

6. A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Pass-a-Grille
9.6 out of 10, Exceptional, (17 reviews)
"Great location for walking to beach and local restaurants. Prefect size for my family of four."
United States
Melissa G
$332 nightly
The price is $372
Sep 30 - Oct 1
Total with taxes and fees
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
A beach with a sandy shore, a few people, and buildings in the background.

7. Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
Pass-a-Grille
9.2 out of 10, Wonderful, (10 reviews)
"Perfect little space. Clean, comfortable and you just can't beat the location. Lisa was a joy to work with. "
United States
Laura P.
$231 nightly
The price is $258
Sep 27 - Sep 28
Total with taxes and fees
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
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

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

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

10/10 Excellent
"After an anniversary trip last year and then again in May with our family, my husband and I returned again for our Anniversary! Everything was superb, especially the water pressure from the shower head!! That felt so good after our 14 hour drive!! Right on the beach and not too crowded! Our kids were jealous they couldn’t come back this time. We can’t wait to come back again with the family!"
Bonnie L. 3-night trip
Posted 2 days ago
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Find out more about Longboat Key

Longboat Key Guest Houses information

Number of reviews
375
Accommodation
0 Guest Houses
Lowest Price
$184
Highest Price
$372

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