A crowded beach with people sunbathing and swimming.

Search Guest Houses in Southwest Florida

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Southwest Florida guest houses

1. Serene Stays Naples

Serene Stays Naples
3.0 star property
Rural Estates
The price is ¥16,876
¥18,732 total
includes taxes & fees
Sep 7 - Sep 8
Serene Stays Naples

2. TriLuxe Inn & Studios

TriLuxe Inn & Studios
2.0 star property
Iona
8.2 out of 10, Very Good, (23 reviews)
"Honestly, not a bad place to stay for a short trip. Nice and clean rooms but very bad water pressure "
United States
Abigail
The price is ¥10,626
¥16,901 total
includes taxes & fees
Oct 1 - Oct 2
TriLuxe Inn & Studios

3. Cozy serene affordable loft in a quiet neighborhood 15-20 minutes to the beach!

Cozy serene affordable loft in a quiet neighborhood 15-20 minutes to the beach!
Naples
10.0 out of 10, Exceptional, (24 reviews)
"Clean loft studio with a short drive to the beach or historic naples! We had a great stay!"
United States
Brittney
The price is ¥12,501
¥30,010 total
includes taxes & fees
Sep 19 - Sep 20
Cozy serene affordable loft in a quiet neighborhood 15-20 minutes to the beach!

4. Summerwind Studios

Summerwind Studios
2.0 star property
Iona
8.2 out of 10, Very Good, (15 reviews)
"Average amenities, spacious room. Support was always available and helpful when needed for check in or TV advice."
United States
Jay
The price is ¥10,626
¥16,901 total
includes taxes & fees
Oct 1 - Oct 2
Summerwind Studios

5. White Orchid Apartments

White Orchid Apartments
2.0 star property
Iona
8.4 out of 10, Very Good, (58 reviews)
"Super clean, had everything you need, easy access and departure, good location."
United States
Laura
The price is ¥10,095
¥16,311 total
includes taxes & fees
Oct 1 - Oct 2
White Orchid Apartments

6. The Palmetto Inn

The Palmetto Inn
3.0 star property
Downtown Boca Grande Historic District
8.2 out of 10, Very Good, (125 reviews)
"Wow! Such a great place to stay! Everything was great! The location is the best! Everything was so clean and new. We’re already planning our next stay here. I highly recommend it."
United States
GARY
The price is ¥25,783
¥28,749 total
includes taxes & fees
Sep 7 - Sep 8
The Palmetto Inn

7. 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.
The price is ¥17,579
¥39,093 total
includes taxes & fees
Sep 8 - Sep 9
Close to Siesta Key beach with a hot tub and a large garden

8. 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
The price is ¥16,243
¥28,367 total
includes taxes & fees
Sep 7 - Sep 8
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

9. Luxe King Studio Near AMI! Beach Gear & Fast WiFi - Double Room

Luxe King Studio Near AMI! Beach Gear & Fast WiFi - Double Room
Bradenton
The price is ¥10,869
¥58,574 total
includes taxes & fees
Sep 7 - Sep 8
Luxe King Studio Near AMI! Beach Gear & Fast WiFi - Double Room

10. 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.
The price is ¥23,439
¥55,707 total
includes taxes & fees
Sep 8 - Sep 9
Siesta key Guest House 5 star on the water Private

11. Cozy studio "glamping" shack 2 miles from Englewood Beach!

Cozy studio "glamping" shack 2 miles from Englewood Beach!
Englewood Central
8.8 out of 10, Excellent, (6 reviews)
"Wonderful place hosted by a very nice family"
United States
Stephen T.
The price is ¥11,720
¥29,924 total
includes taxes & fees
Sep 15 - Sep 16
Cozy studio "glamping" shack 2 miles from Englewood Beach!

12. 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.
The price is ¥17,790
¥33,719 total
includes taxes & fees
Sep 7 - Sep 8
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

13. Shad Room - Cozy Private Bedroom in a Shared Home

Shad Room - Cozy Private Bedroom in a Shared Home
2.0 star property
Sebring
The price is ¥10,065
¥23,277 total
includes taxes & fees
Sep 8 - Sep 9
Shad Room - Cozy Private Bedroom in a Shared Home

14. With Oasis Shared Backyard

With Oasis Shared Backyard
Lake Maggiore Shore
8.2 out of 10, Very Good, (36 reviews)
"Just stayed onenight. Will stay again"
United States
Glen V.
The price is ¥14,688
¥23,254 total
includes taxes & fees
Sep 11 - Sep 12
With Oasis Shared Backyard

15. 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.
The price is ¥16,126
¥40,451 total
includes taxes & fees
Sep 22 - Sep 23
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

16. 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
The price is ¥17,956
¥53,283 total
includes taxes & fees
Sep 9 - Sep 10
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

17. Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio
Historic Old Northeast
9.8 out of 10, Exceptional, (18 reviews)
"The property was great and exactly what we needed! The location was within walking distance to so may great spots and the guide Lisa provided was super helpful."
United States
Phoebe A.
The price is ¥12,001
¥29,401 total
includes taxes & fees
Sep 7 - Sep 8
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

18. Tree Top Getaway- Sleeps 4

Tree Top Getaway- Sleeps 4
Gulfport
9.0 out of 10, Wonderful, (8 reviews)
"Fun little property for a weekend getaway!"
United States
Charlotte C.
The price is ¥20,373
¥35,218 total
includes taxes & fees
Sep 7 - Sep 8
Tree Top Getaway- Sleeps 4

19. Largo Palms Suite by Indian Rocks Beach

Largo Palms Suite by Indian Rocks Beach
Orange Lake Village
The price is ¥6,472
¥28,097 total
includes taxes & fees
Sep 7 - Sep 8
Largo Palms Suite by Indian Rocks Beach

20. 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, (42 reviews)
"Perfect place for a getaway"
United States
Barbara F.
The price is ¥15,551
¥45,215 total
includes taxes & fees
Sep 13 - Sep 14
Charming Cottage in Pass-A-Grille Beach, Dogs 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Florida Hotel Reviews

Find out more about Southwest Florida

Southwest Florida Guest Houses information

Number of reviews
648
Accommodation
7 Guest Houses
Lowest Price
¥16,311
Highest Price
¥58,574

Explore a world of travel with Expedia