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

Search Guest Houses in Longboat Key

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6

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.
$186 nightly
The price is $217
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, (138 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
$163 nightly
The price is $182
Oct 7 - Oct 8
Total with taxes and fees
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball
A beach with a sandy shore, a few people, and buildings in the background.

3. 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.
$251 nightly
The price is $280
Oct 7 - Oct 8
Total with taxes and fees
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes
A covered outdoor deck with a ceiling fan, wooden railing, and a seating area with cushions.

4. 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 7 - Oct 8
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.

5. 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.
$225 nightly
The price is $250
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.

6. 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, (46 reviews)
"Perfect place for a getaway"
United States
Barbara F.
$295 nightly
The price is $329
Oct 13 - Oct 14
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.

7. 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
$325 nightly
The price is $363
Oct 7 - Oct 8
Total with taxes and fees
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
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

Spacious 3BR Gulfside Condo – Silver Sands #238 by RVA

Spacious 3BR Gulfside Condo – Silver Sands #238 by RVA

10/10 Excellent
"Condo was wonderful and location was incredible. Had the beach to ourselves for most of the week! Just be aware that while the property is oceanfront, this condo does not overlook the ocean. You are behind the main building that faces the beach."
Taylor H. 7-night trip
Posted 4 days ago
Spacious 3BR Gulfside Condo – Silver Sands #238 by RVA

Find out more about Longboat Key

Longboat Key Guest Houses information

Number of reviews
378
Accommodation
0 Guest Houses
Lowest Price
$182
Highest Price
$363

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