Holiday Homes in Naples

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Naples

Luxe, waterfront home with pool, spa, dock & gorgeous backyard

9.6 out of 10, Exceptional, (13)
"Absolutely beautiful home with gorgeous pool and view of the canal! We even got to see dolphins 3 of our days during the week which was an extra special surprise!!"
Luxe, waterfront home with pool, spa, dock & gorgeous backyard

Beautiful home with private pool & lanai - near beaches & parks

8.6 out of 10, Excellent, (38)
"The house is adorable, close to everything. Easy check in and out process. Has everything you need. The pool was beautiful. The only downside is there is a house directly in back of the pool that is occupied so there is no privacy at all when your on the lanai or in the pool. "
Beautiful home with private pool & lanai - near beaches & parks

Private Waterfront home with pool and hot tub with large dock in Isle of Capri

9.4 out of 10, Exceptional, (78)
"We really enjoyed our month stay. Daniel was very helpful and loved the views and watching the dolphins. Will definitely go back. "
Private Waterfront home with pool and hot tub with large dock in Isle of Capri

Lovely Naples Home: Backyard Oasis w/ Pool!

9.6 out of 10, Exceptional, (14)
"This rental was not intended. Our previous rental was unsafe for my special needs son. So for only 3 of us, this was a lot of house. However, it is located in a very nice neighborhood. There are lots of great things in the area. The house was very clean and welcoming. It felt like home away from home. The pool was very nice! We were excited to FaceTime the rest of our family back home to show them how incredible it was, so when we all come back we can rent this place again! I would highly...
Lovely Naples Home: Backyard Oasis w/ Pool!

Luxurious 4-Bed Pool Home with Dock & Gulf Views

10.0 out of 10, Exceptional, (124)
"Beautiful home with impressive view. Can’t wait to book it again. The house was spotless and was better than it showed online !"
Luxurious 4-Bed Pool Home with Dock & Gulf Views

6 Bedrooms 4 baths Dream Pool Home near Vanderbilt Beach Naples Florida

9.4 out of 10, Exceptional, (18)
"Great stay. Maybe more bath towels would be nice but otherwise we had a wonderful time and any questions we had were addressed in a very timely manner"
6 Bedrooms 4 baths Dream Pool Home near Vanderbilt Beach Naples Florida

Key West Style Luxury Home with resort style heated pool and infinity line spa

9.8 out of 10, Exceptional, (126)
"So much to do in the back yard … pool, hot tub, dining poolside and swim up table in the pool!! Plenty of sun loungers AND ample spots in the shade of the palm and oak trees! Loved the screened lanai for meals, family card games and morning relaxing! "
Key West Style Luxury Home with resort style heated pool and infinity line spa

APRIL 2025 AVAILABLE! YOUR OASIS! NEWER home w/ POOL. 4 miles to Beach&downtown!

9.8 out of 10, Exceptional, (76)
"Me and my cousin stayed here for a week, clean nice house in a very nice neighborhood. Pool was warm, we enjoyed biking nearby public parks, going to naples beach thats only 15 mins away, and walking around the sidewalks of neighborhood "
APRIL 2025 AVAILABLE! YOUR OASIS! NEWER home w/ POOL. 4 miles to Beach&downtown!

Secluded Beach Retreat: Bonita Beach Coastal Gem

9.2 out of 10, Wonderful, (13)
"The house had large spaces for gathering, well equipped kitchen and very convenient to beach. "
Secluded Beach Retreat: Bonita Beach Coastal Gem

ISLAND LIFESTYLE FAMILY VACATION HOME (BRAND NEW)

10.0 out of 10, Exceptional, (64)
"This home was just as advertised and better. The home is on a quiet residential street with beautiful homes and cute islandy restaurants nearby. This home was stocked with all the essentials..laundry and dish detergent, paper towels,sponges etc. All appliances are like new, beautiful pool and private lanai, comfy beds, barbecue grill and a garage filled with bikes and beach items. Short 10 minute drive to Marco and about 30 minutes to downtown Naples.We loved our time here and wish we could have...
ISLAND LIFESTYLE FAMILY VACATION HOME (BRAND NEW)

Renovated snowbird-friendly home with private heated pool, pool spa, gas grill

9.4 out of 10, Exceptional, (44)
"Lives the house. Clean, great pool, great location. Sauna never seemed to get hot unfortunately. Overall would def recommend "
Renovated snowbird-friendly home with private heated pool, pool spa, gas grill

Newly Renovated Private Pool Home -Minutes to Bonita Beach. Quiet location.

10.0 out of 10, Exceptional, (58)
"Perfect location near beaches, grocery stores, and restaurants. The house had everything we needed, including lots of beach towels, beach chairs and toys. The home was well stocked from the kitchen and bathrooms, to even providing laundry detergent. The pool and back patio were private, beautifully landscaped making for a relaxing place to hang out. Great neighborhood to enjoy a morning run/walk. We all enjoyed our stay for spring break, will definitely stay here again."
Newly Renovated Private Pool Home -Minutes to Bonita Beach. Quiet location.

* * Endless Summer * * Beach. Unique. Comfort.

9.2 out of 10, Wonderful, (12)
"Great house within walking distance to Vanderbilt Beach. Very clean and comfortable. Host was very responsive. Would stay there again!"
* * Endless Summer * * Beach. Unique. Comfort.

Charming 3-bedroom house in Hickory Bay- on water-North Naples- Bonita Springs-

10.0 out of 10, Exceptional, (5)
"Great location with lots of places to walk for food and bait, etc... Very up and coming neighborhood. The outdoor space was way bigger than it presents in pictures. Great pool and hot tub and several conversation areas. The canal access was easy and fun to explore. We judge everything on if we could live there and we could. The indoor space is very large and open and super comfortable. The bedrooms are a bit small and close to each other but still fine because you have plenty of other...
Charming 3-bedroom house in Hickory Bay- on water-North Naples- Bonita Springs-

New! Sunkissed - 1 Mile to Beach! Heated Pool!

10.0 out of 10, Exceptional, (3)
"The house was lovely, with lots of living space and a beautiful screened-in pool and patio. We had a couple of quick questions for the manager, and received the answers very promptly. Handy location for Vanderbilt Beach. Kitchen very well stocked with cookware, dishware, utensils/knives and storage containers. Overall, had a great stay."
New! Sunkissed - 1 Mile to Beach! Heated Pool!

Peaceful home next to the best restaurants, BEACHES... $5 CLEANING

9.6 out of 10, Exceptional, (59)
"The unit has a great location, close to the beach and restaurants. 1 block from the American legion. Unit has all the amenities of home. The host was so kind and available if needed. Would happily stay again in the future. "
Peaceful home next to the best restaurants, BEACHES... $5 CLEANING

Elegant guest suite with a Dock and Pool

10.0 out of 10, Exceptional, (86)
"We had a very nice time and the place was very clean. I wish we could’ve met up with Scott and Bre a little bit more but we’ll have to do that next time! Thank you for a good time."
Elegant guest suite with a Dock and Pool

Bonita Beach Mansion, New Constuction Home, Pool, Spa, Bikes and Near Beach

9.8 out of 10, Exceptional, (22)
"Beautiful home, great space for a multi-generational family stay. Overall very comfortable with upscale features, including spa-like bathrooms. The whole family really enjoyed the pool and hot tub!"
Bonita Beach Mansion, New Constuction Home, Pool, Spa, Bikes and Near Beach

Charming Beach Cottage with private Pool&Spa! Walk to stunning Vanderbilt Beach

10.0 out of 10, Exceptional, (271)
"Nice place to stay with a family! "
The price is NZ$664
includes taxes & fees
19 May - 20 May
Charming Beach Cottage with private Pool&Spa! Walk to stunning Vanderbilt Beach

Charming Bungalow, remodeled, heated pool, walk to the beach

9.8 out of 10, Exceptional, (58)
"Everything about the home was as advertised! We really enjoyed the heated pool! The neighborhood was quiet but beach access was farther than we expected, about 2 miles or so! The beach around the area was very busy and parking difficult to come by! Make sure you get to the beach early morning by 10 or so or you won’t find a place to park! Host Stacey was very responsive to our questions! Not a lot of places to walk too! Overall we loved this home! One mattress on the bed was terrible and very...
Charming Bungalow, remodeled, heated pool, walk to the 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.
Don't see what you're looking for?
See all available properties in Naples
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Naples

Bellasera Resort

4.0 star property
9.6 out of 10, Exceptional, (2146)
"We loved our stay at Bellasera so much and can't wait to stay here again. Room was huge (895 SF) and we had a full kitchen and a washer/dryer, plus a dining room, living room, and enclosed balcony that also had a table and 4 chairs. The staff was great! The concierge got us a reservation for dinner at a "very hard to get reservations" restaurant! The free shuttle service that will take you and pick you up until 11 at night is amazing! 5-minute walk to 5th Avenue. 5 stars!"
The price is NZ$847
includes taxes & fees
27 Apr - 28 Apr
Bellasera Resort

Wiggins Pass Chalet

4.0 star property
9.8 out of 10, Exceptional, (208)
"Host was super friendly and helpful. "
The price is NZ$304
includes taxes & fees
1 May - 2 May
Wiggins Pass Chalet

GreenLinks Golf Villas at Lely Resort

3.0 star property
9.4 out of 10, Exceptional, (515)
"Clean "
The price is NZ$477
includes taxes & fees
27 Apr - 28 Apr
GreenLinks Golf Villas at Lely Resort
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.