Holiday Homes in Southwest Florida

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Featured Holiday Homes in Southwest Florida

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

8.0 out of 10, Very good, (1)
"The Bar and pool makes this place Had a great time"
The price is AU$264
includes taxes & fees
14 Jan - 15 Jan
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

The Sonset Updates Throughout Private pool near Vanderbilt Beach &Delnor Wiggins

10.0 out of 10, Exceptional, (92)
"This was our first trip to Naples and it certainly won’t be our last. Beau’s property was absolutely perfect for our family of three. The location was outstanding and the house had everything we needed. Before we even arrived, Beau was incredibly proactive in communicating a potential issue with the pool heater and even preemptively issued a refund for heater fee for any inconvenience. The master bed was very comfortable, which is rare in rental properties. We’re so glad to know we’ve found a...
The Sonset Updates Throughout Private pool near Vanderbilt Beach &Delnor Wiggins

Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

10.0 out of 10, Exceptional, (29)
"A quick stay with a good friend on our way to a family wedding further south in Florida. We enjoyed the lovely cottage - it was decorated beautifully and very comfortable. I am in love with the bath wallpaper!!! My only suggestion is to add hand soap in the bathrooms, and to have a non-dairy creamer/sugar for those that may want it. The owner was very good with communication and let us know that we could check in early as there wasn't a guest on our arrival day. We enjoyed exploring Bradenton...
The price is AU$649
includes taxes & fees
15 Jan - 16 Jan
Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

Updated home with enclosed pool, open layout, grill, W/D, streaming, and AC

9.8 out of 10, Exceptional, (10)
"The house was very nice "
Updated home with enclosed pool, open layout, grill, W/D, streaming, and AC

Private Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (218)
"Nice house. Very very clean. Owners were quick with response to questions. "
Private Pool House 6 miles from the Beach

Beautiful waterfront home with pool, game room, & dog-friendly

9.4 out of 10, Exceptional, (19)
"Very roomy, quiet neighborhood and close to restaurants. We will be back"
Beautiful waterfront home with pool, game room, & dog-friendly

Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes

10.0 out of 10, Exceptional, (129)
"The house at Cape Coral was beautiful and had everything we needed. It was very comfortable and clean. The pool and hot tub were a great way to relax in the evening after a great day of boating and time on the beach. The owners were very responsive and were excellent with communication and a genuine desire to make our stay wonderful. Will definitely stay again. clean. The pool and hot tub we "
Gulf Canal, Boat Rental, Hot tub, Pool, Kayaks, & Bikes

Tropical Retreat in Southwest Cape Coral

9.8 out of 10, Exceptional, (44)
"This house was exceptional! Split floor plan, new furnishings, spotlessly clean, pool heated to 87 degrees, hot tub available, washer/dryer. Peter was great at communicating. No major issues and this house was gorgeous in a great neighborhood on Cape Coral. Would most definitely stay there again. TY so much Peter! Loved it."
Tropical Retreat in Southwest Cape Coral

Located in the heart of Old Naples! Enjoy the beach shopping and dining

10.0 out of 10, Exceptional, (13)
"Within walking distance of the beach and many restaurants. Carla provides everything you need for the beach. We would stay here again without hesitation."
Located in the heart of Old Naples! Enjoy the beach shopping and dining

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (220)
"Beautiful Villas close to beach and shopping!"
Tropical Villas of Venice Beach

Villa 17 BREATHTAKING VIEWS! Salt Water Pool 30 Reviews!

9.8 out of 10, Exceptional, (43)
"Would stay again"
Villa 17 BREATHTAKING VIEWS! Salt Water Pool 30 Reviews!

Unharmed by Milton! Closest Vacation Cottage to Vanderbilt Beach priv. Pool&Spa

10.0 out of 10, Exceptional, (258)
"Cozy cottage in nice neighborhood, close to beach and shopping"
The price is AU$799
includes taxes & fees
20 Jan - 21 Jan
Unharmed by Milton! Closest Vacation Cottage to Vanderbilt Beach priv. Pool&Spa

Cute Bungalow close to downtown and Anna Maria Island.

9.6 out of 10, Exceptional, (18)
"Was just right for what we needed and what we expected for the price. "
Cute Bungalow close to downtown and Anna Maria Island.

Villa 1, Spacious, Hot Tub, Saltwater Htd Pool 136 reviews

10.0 out of 10, Exceptional, (152)
"Property is very nice, great location, very accessible, affordable, and the manager was pleasant. Enjoyed our stay"
Villa 1, Spacious, Hot Tub, Saltwater Htd Pool 136 reviews

Cozy Studio in Quiet Neighborhood

8.4 out of 10, Very good, (7)
"Having lived in both Bradenton and SRQ many years I was surprised at both location and size of stay. It was literally a one car garage, completely turned into a vrbo. For a week or less very doable. But for the whole month of Feb. a little too small and inconvenient."
The price is AU$271
includes taxes & fees
11 Jan - 12 Jan
Cozy Studio in Quiet Neighborhood

Paradise Naples Pool Home. Free headed pool

10.0 out of 10, Exceptional, (15)
"The inside of the house was beautiful. Great family room and pool area. The master is gorgeous. Very clean. "
Paradise Naples Pool Home. Free headed pool

Tranquil home near golf with heated pool/spa, high-speed WiFi & central AC

8.6 out of 10, Excellent, (32)
"The air conditioning did not work. "
Tranquil home near golf with heated pool/spa, high-speed WiFi & central AC

3/2 Home steps away from Tiger Tail access

8.8 out of 10, Excellent, (21)
"I will start with the pros. 1. Excellent, walkable location to Tigertail beach. 2. Beach chairs, cooler and beach towels provided plus some floaties for the pool. 3. Kitchen was well stocked with dishes, glasses, cookware and spices etc. 4. Fishing dock with chairs and grill on patio. Cons 1.Rental agency, though very quick to respond to any questions, deferred any issues with rental stating they would "let the owner know". This was fairly frustrating when we were left to repair any issues...
3/2 Home steps away from Tiger Tail access

NEW - Close to MERCATO & BEACH Designer Pool Home on Estate Lot! 3+bedrooms!

9.8 out of 10, Exceptional, (57)
"Yulia’s property is wonderful and she is very accommodating! We will definitely be back again for a repeat stay."
NEW - Close to MERCATO & BEACH Designer Pool Home on Estate Lot! 3+bedrooms!

Quiet Naples Home: Walking Distance to Downtown w/ 2 Bicycles. Pet Friendly!

9.8 out of 10, Exceptional, (8)
"The stay was great, host are very commutative and helpful if at all needed. Property was exactly as advertised! Great location and environment, definitely recommend. I did not need the second bedroom, but for a family this is a great get away stop!"
The price is AU$651
includes taxes & fees
6 Jan - 7 Jan
Quiet Naples Home: Walking Distance to Downtown w/ 2 Bicycles. Pet Friendly!
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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Other property types in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (704)
"Very enjoyable stay!"
The price is AU$537
includes taxes & fees
12 Jan - 13 Jan
The Suites at Fishermen’s Village- 2 Bedroom Suites

Bellasera Resort

4.0 star property
9.6 out of 10, Exceptional, (2076)
"The hotel is walkable to shopping and dining. Very quiet. Friendly staff. There is a shuttle that will take you within a few miles of the hotel. Free bicycles. Great food in the restaurant but there are many food options close by. Two bedroom condo was huge and immaculate. "
The price is AU$884
includes taxes & fees
4 Jan - 5 Jan
Bellasera Resort

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
9.2 out of 10, Wonderful, (491)
"This property is incredible. We had such a wonderful stay. The room was phenomenal. The facilities were beyond wonderful. Our family had a great trip "
The price is AU$454
includes taxes & fees
15 Jan - 16 Jan
Hyatt Vacation Club at Coconut Cove, Bonita Springs
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.