Holiday Homes in Naples

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Featured Holiday Homes in Naples

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

9.6 out of 10, Exceptional, (12)
"We had a great stay over Christmas! The pool and spa were used morning and night by the kids and adults! Love the outdoor area where the adults can relax while the kids swim! Can’t wait to go back!"
Luxe, waterfront home with pool, spa, dock & gorgeous backyard

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

8.8 out of 10, Excellent, (37)
"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

9.2 out of 10, Wonderful, (77)
"Love this property! You can walk to restaurants and the marina, short drive to Marco beaches."
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, (12)
"The space was great for our 3 family group. Enough space for everyone to have a quiet spot. The pool area could use a good cleaning. The grill needs to be replaced, fire hazard. The freezer would leak water from the inside onto the floor, had to keep a towel underneath. There was a septic issue that was resolved as fast as the owner could get someone out there. "
Lovely Naples Home: Backyard Oasis w/ Pool!

Luxurious 4-Bed Pool Home with Dock & Gulf Views

10.0 out of 10, Exceptional, (121)
"What a little piece of paradise. The setting was just spectacular. Nightly sunsets and daily fishing (and dolphin spotting) from the dock. Home was immaculately clean. "
Luxurious 4-Bed Pool Home with Dock & Gulf Views

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

9.2 out of 10, Wonderful, (15)
"My wife and I along with our three adult children, their three spouses and our 5 grandchildren enjoyed a great week at this VRBO. The home was very clean at check in, had plenty of space and provided for a great family vacation! The location is minutes to the beach as well as all of your shopping needs. We would rent again if headed to Naples! "
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, (124)
"Home is beautiful and spacious. Hot tub and pool are great! It’s like having your own resort. I stayed there with my husband, children and grandchildren. Everything you need for them, Beth has! They loved the Frozen playroom. We enjoyed our stay and hope to return again someday."
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, (61)
"This house and its host were great. Plenty of stock of everything…. We grilled on the grill swam in the heated pool, walked to the bars, and drove to the beaches. If you want a little quieter off the island this is your place. Great for walking biking and 2 miles to Marco and 5 miles to south Naples. Would go back in a second…. Great TV accommodations for night timesports watching."
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, (43)
"Probably the best, updated, clean houses we’ve ever rented! It was absolutely wonderful. And the added cost to heat the pool and hot tub was totally worth it. Had to contact the management to figure out how to turn on hot tub and heat it up, and they instructed me to download the app and once I did that I had control of the lights and turning the spa on and off. Kids absolutely loved it. And the location is incredible. Quiet neighborhood and close to so many restaurants and shopping as well as...
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, (55)
"Good access to beaches, state parks, and amenities "
Newly Renovated Private Pool Home -Minutes to Bonita Beach. Quiet location.

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

9.4 out of 10, Exceptional, (10)
"We side this property for overflow and WFH guests (we live nearby). Perfect for both!"
* * 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, (57)
"Very nice place. "
Peaceful home next to the best restaurants, BEACHES... $5 CLEANING

Elegant guest suite with a Dock and Pool

10.0 out of 10, Exceptional, (84)
"We had an amazing vacation and this property was wonderfully located and an Oasis with it's privacy and amenities. We would definitely stay here again!!!"
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, (267)
"As others have said, the place is as advertised. Host is great and communicates timely. Any issues were addressed right away. We could easily walk to the beach and the house comes with anything you need. Thanks!"
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, (56)
"Lovely cottage"
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.
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Other property types in Naples

Bellasera Resort

4.0 star property
9.6 out of 10, Exceptional, (2132)
"Excellent property and service. Highly recommended!"
The price is NZ$1,172
includes taxes & fees
6 Apr - 7 Apr
Bellasera Resort

Wiggins Pass Chalet

4.0 star property
9.8 out of 10, Exceptional, (202)
"Great location. We were a little early and our room wasnt ready. Autum offered us beach chairs an directions to a beautiful beach location. A perfect spot to relax after a long day of travel. She also recomended a great place to have dinner. Will return as everything was A ."
The price is NZ$359
includes taxes & fees
2 Apr - 3 Apr
Wiggins Pass Chalet

GreenLinks Golf Villas at Lely Resort

3.0 star property
9.4 out of 10, Exceptional, (513)
"We had a wonderful time!!"
The price is NZ$568
includes taxes & fees
12 Apr - 13 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.