A crowded beach with people sunbathing and swimming.

Search Guest Houses in Southwest Florida

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • 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
"Our stay at Serene Stays Naples was very pleasant. We loved the well stocked, modern kitchen and very comfortable beds. Definitely will return."
United States
Nanette
The price is £85
includes taxes & fees
5 Oct - 6 Oct
Serene Stays Naples

2. TriLuxe Inn & Studios

TriLuxe Inn & Studios
2.0 star property
Iona
8.2 out of 10, Very good, (23 reviews)
"Everything was great, will definitely be coming back"
United States
Ruben
The price is £81
includes taxes & fees
1 Oct - 2 Oct
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 £149
includes taxes & fees
25 Sept - 26 Sept
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 £81
includes taxes & fees
1 Oct - 2 Oct
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 £78
includes taxes & fees
8 Oct - 9 Oct
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, (126 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 £109
includes taxes & fees
27 Sept - 28 Sept
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 £191
includes taxes & fees
21 Sept - 22 Sept
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 £139
includes taxes & fees
21 Sept - 22 Sept
Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

9. 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 £145
includes taxes & fees
27 Sept - 28 Sept
Cozy studio "glamping" shack 2 miles from Englewood Beach!

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 £271
includes taxes & fees
1 Oct - 2 Oct
Siesta key Guest House 5 star on the water Private

11. 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 £165
includes taxes & fees
8 Oct - 9 Oct
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

12. 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 £197
includes taxes & fees
21 Sept - 22 Sept
Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

13. 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 £139
includes taxes & fees
24 Sept - 25 Sept
Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

14. Largo Palms Suite by Indian Rocks Beach

Largo Palms Suite by Indian Rocks Beach
Orange Lake Village
The price is £142
includes taxes & fees
21 Sept - 22 Sept
Largo Palms Suite by Indian Rocks Beach

15. 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 £280
includes taxes & fees
24 Sept - 25 Sept
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

16. 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 £175
includes taxes & fees
21 Sept - 22 Sept
Tree Top Getaway- Sleeps 4

17. 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, (43 reviews)
"This place is adorable also properly stocked and very clean . The location is great! We thoroughly enjoyed are stay. I will be staying again in the next few weeks!"
United States
Julie R.
The price is £245
includes taxes & fees
25 Sept - 26 Sept
Charming Cottage in Pass-A-Grille Beach, Dogs Ok

18. Walk to The Beach, shops and restaurants, The sweetest place is “The Sweet”

Walk to The Beach, shops and restaurants, The sweetest place is “The Sweet”
Largo
10.0 out of 10, Exceptional, (62 reviews)
"Nice place to stay. It’s 1 mile from the beach and lots of good food options close by. "
United States
Max W.
The price is £194
includes taxes & fees
21 Sept - 22 Sept
Walk to The Beach, shops and restaurants, The sweetest place is “The Sweet”

19. Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Steps to Beach, Heated Pool, 2 Queen Beds, 2BA
Madeira Beach
The price is £214
includes taxes & fees
24 Sept - 25 Sept
Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

20. Largo Palms House by Indian Rocks Beach

Largo Palms House by Indian Rocks Beach
Orange Lake Village
The price is £262
includes taxes & fees
30 Sept - 1 Oct
Largo Palms House by Indian Rocks Beach
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
676
Accommodation
7 Guest Houses
Lowest Price
£78
Highest Price
£280

Explore a world of travel with Expedia