5 Vacation Rentals You Wish You Had Booked

Did you know that a weekly vacation rental is likely to be less expensive than staying in a single hotel room for 7 nights? Don’t get me wrong, I love a luxury hotel room just as much as the next girl. Who doesn’t appreciate fresh towels every day?! Not to mention the chocolates left on your pillow for turn down service and a bathroom stocked with complimentary brand-name toiletries. But when you travel with your family, somewhere around the time you go from a king-sized bed to two double beds and a rollaway, it stops being fun to share a single room. Or maybe it was never that great.

When you rent a whole house there is the potential for everyone to have their own room. At best you won’t have to share with your kids. There will be a kitchen, which can save you money if you choose to prepare your meals at home. A central living space allowing for a place to hang out rather than on your hotel beds. There is usually free parking and no fee for the wi-fi. Plus extra amenities can include a private pool, outdoor living space, and laundry facilities.

More often than not nowadays when we plan family vacations, our preferred accommodation choice is a rental home. These are just a few of our recent favorites from the last few years.

Cape Cod, Massachusetts

Orleans Vacation Rental

The first time we rented a house, we stayed in this little gem. Centrally located on the Cape in the town of in Orleans, it was the perfect place for a summer vacation with another family. The master and another bedroom share a bathroom upstairs. A little strange if you aren’t super close to the other guests. On the main floor, there are two additional bedrooms. There is an option to rent the attached studio giving you five bedrooms total and enough space to sleep ten people. While it is not oceanfront, the master bedroom has a limited view of the Atlantic and Nauset Beach is a short walk down the road. This house is stunning on the inside and really feels like a home, not a rental. The property is tastefully decorated with the owner’s artwork and furnishings. It made us want to spend just as much time at the house as we did out exploring or on the beach.

Pro Tip: In this home, we appreciated the large outdoor living space and the fact that the kitchen came fully stocked with spices, cleaning supplies, and other basic necessities. This isn’t always the case with vacation rentals.

Eleuthera, Bahamas

Eleuthera Vacation Rental

My family is still talking about the 2-bedroom home we rented on Eleuthera. We would love to stay there again someday. With a white color palette, clean lines and trendy furnishings this modern beach house was just our style. Although it does not have ocean views the home’s central location on the island more than made up for it. Eleuthera is 110 miles long and in some places no more than a mile wide. Governor’s Harbor, where the house is located, is the midway point of Eleuthera. This gave us easy access to the main airport and the ability to explore many of Eleuthera’s beautiful beaches. The house also had a private pool which we took advantage of in the late afternoons.

Pro Tip: The hosts of this home live nearby and couldn’t have been more welcoming. The first night we arrived they even left a homemade meal for us in the fridge. A welcome treat after a long day of travel. Throughout our stay, they also dropped off fresh veggies from their garden.

Anna Maria Island, Florida

Anna Maria Island Vacation Rental

One Thanksgiving my extended family rented the Beach Villa on Anna Maria Island. Located a short two block walk from the beach it made it easy to go back and forth during the day. With five bedrooms and four and a half baths, there was plenty of room for the eleven of us. The master bedroom is on the main level of the house along with the living room, kitchen, and dining room. The outdoor space is made for families to enjoy. There is a heated pool, jacuzzi, lots of seating and a wet bar with flat screen television.

Pro Tip: With such a large group it was much easier to eat in rather than go out. Although there is a Publix supermarket just down the road from this home, we recommend checking out the upscale Fresh Market in nearby Bradenton. You can even pre-order online for in-store pick-up.

Edinburgh, Scotland

Edinburgh Vacation Rental

The Writer’s Pad is all about the location. This two-bedroom, New Town flat is in an excellent spot for exploring Edinburgh. Our family of four was very comfortable in this vacation rental. The smaller, front bedroom has a double bed, while the larger back bedroom has two twins that can be joined together as a king bed if need be. The kitchen is very small, but that didn’t bother us as we weren’t making meals on this trip. We just stocked it with coffee and breakfast provisions. There is a washer but no dryer. You can either hang dry your clothing outback or from a clever rack that drops down from the hallway ceiling. There is only one modest, but functional bathroom, so you will need to share.

Pro Tip: This apartment just two blocks from the bustling Broughton Street which is home to great shops and restaurants. I highly recommend Asti for great Italian food. Make a reservation though as it tends to get crowded. We also walked to Hanover Street where you can catch the hop-on-hop-off bus. Rather than use taxis, we purchased a 24-hour bus pass for our family to help us get around and see the city.

Sayulita, Mexico

Sayulita Vacation Rental

Perched high on a hill above the town of Sayulita, Casa Angel has spectacular ocean views from almost every room in the house. There are 3 bedrooms, each with their own bathroom. Two of the bedrooms are located upstairs and one is on the main floor with direct access to the patio and pool area. There is a well-equipped kitchen with filtered water from the taps and refrigerator. It is a bonus in Mexico not to have to buy bottled water.

This was the first time our vacation rental included maid service. This is a luxury I will look for in future rental properties. It was nice to have everything tidied up daily. There home also comes with an English speaking caretaker who was readily available to help us and seemed to know everything about Sayulita.

Pro-Tip: Sayulita’s cobblestone hillsides are very steep. If you plan to rent a car, do not get one with a low front bumper. It is very easy to bottom out and cause damage to the car. We barely used ours. It is a five-minute walk down the hill and into town.

Commenting area

  1. Love the post! Makes me wanna pack up and just leave hehe

  2. I love the destinations and the photos. I will look into vacation rentals that include a maid service as well!

    • Dana Freeman May 30, 2016 at 1:57 pm · · Reply

      Yes to Maid Service! It really made it feel like I was on vacation, not just doing all the same chores I do at home 🙂

  3. These are great!!

  4. I have been in Casa Angel, it´s a fantastic place! And Sayulita is lovely.

    • Dana Freeman June 10, 2016 at 5:50 pm · · Reply

      Isn’t it lovely. And in an odd coincidence the owner’s primary resident is here in Vermont!

  5. The stylists one looks absolutely lovely and s great place to stay there

  6. great roundup! i especially love the one with the small pool in the back.


  7. We visit Florida often! Now I have a new place I need to check out! Thanks for sharing 🙂

  8. We love a good vacation rental! Very helpful with a family of 5…

  9. I agree: vacation rentals are the best solution and these look amazing: can I have thatFlorida pool please? My kids would love it!

  10. Great recommendation for Sayulita! We live in Mexico City and have still not visited this beachside town – now I know where to stay when we eventually get there!!

  11. These are great! I’m a BIG fan of Sayulita, Mexico. Will have to check out Casa Angel. Vacation rentals are so the way to go when you’re traveling as a family.

  12. I love the variety of stays you recommend. We are hoping to get to Edinburgh later this year and I’ve noted the Writers Retreat. Sounds like the perfect place we’d stay.

  13. Absolutely! Vacation rentals=happy travel. I love AMI and will try to get that place. Well, I love Cape Cod and the other places, too.

    • Dana Freeman August 24, 2016 at 5:54 pm · · Reply

      I just stayed in another Homeaway Rental in Cape Cod this past July. It was fabulous for a family of 4-6. I will write about it next!

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