Jacksonville, Florida has character, and so do these homes. Happy Day Vacay places guests in the heart of the city's most beloved historic neighborhoods, steps from front porches, original charm, and the local coffee shop, bar, or museum everyone keeps talking about. Each home carries its own story and layout, but they all share the essentials: plush beds, real wifi, and yards big enough for the dog to stretch out. Kids welcome. Pets welcome. Vacation here fits real life, it doesn't ask you to leave it behind.

12 properties  

$139/night

240

OwnerRez
3 Bedrooms • 2 Baths (1 full, 1 half) • Sleeps 8-11
Allows pets Internet
Historic Springfield home with tons of charm and space. Lovely peaceful backyard space, great for entertaining. Home has a large kitchen and entertaining space. There are 4 twins, 1 queen, 2 fold out sofa beds and an air mattress. Approximately 10 min san marco, riverside and other surrounding neighborhoods. 30 min to beaches and St Augustine. 1 mile to Vystar and other arenas.

Photos Details Inquire

$149/night

917

OwnerRez
2 Bedrooms • 1 Bath • Sleeps 5-8
Allows pets Internet
Must be min 25 yrs old. This super stylish 2 bedroom home in San Marco will give you everything you are looking for during your getaway. You will enjoy the open space, large dining area, fun outdoor space, multiple patios, and super plush comfy beds. This triplex is located walking distance to the shops and restaurants of San Marco.

Photos Details Inquire

$159/night

919

OwnerRez
3 Bedrooms • 1 Bath • Sleeps 5-8
Allows pets Internet
Must be min 25 yrs old. You will fall in love with this cozy stylish one level home in San Marco. There is plenty of seating, space and fun shared outdoor areas including 2 private patios at this awesome triplex. The beds are plush comfy beds with nice linens and sound machines will ensure you sleep well. Enjoy the home and walk to nearby shops, restaurants, and bars in the trendy fun San Marco neighborhood.

Photos Details Inquire

$119/night

921

OwnerRez
1 Bedroom • 1 Bath • Sleeps 4-5
Allows pets Internet
Must be min 25 yrs old. This one bedroom home is the perfect space to relax, work or just enjoy some peace! There is lots of open space, plush comfy bed, shared courtyard and excellent location. Enjoy this awesome triplex or take a quick walk and you will be at the shops, restaurants and bars of the trendy San Marco neighborhood in Jacksonville.

Photos Details Inquire

$145/night

1026

OwnerRez
3 Bedrooms • 3 Baths • Sleeps 7-10
Allows pets Internet
Must be min 25 yrs old. This historic Springfield home has been fully renovated & is central to everything fun. Less than 5 min from Vystar & other show venues, less than 30 min from beaches, St Augustine & other areas of Jacksonville. Close to the zoo & museums & the best restaurants & bars in Jacksonville. This home is all one floor and has tons of functional space for a family. Pet & child friendly. You will feel right at home in this lovely cottage style house with tons of amenities.

Photos Details Inquire

$175/night

1142

OwnerRez
3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 7-9
Allows pets Internet
Must be min 25 yrs old. Updated stylish historic home centrally located to everything Jacksonville has to offer. Spacious, family & pet friendly, this home will give you all the cozy feels you are looking for. Plush nectar beds with cotton linens and sound machines in each bedroom ensure you will wake up rested. On & off street parking, large pavered back yard, luscious landscaping & a quiet neighborhood make this a peaceful home to relax, have fun, work remotely or do whatever you desire!

Photos Details Inquire

$139/night

1413

OwnerRez
3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 7-10
Allows pets Internet
Must be min 25 yrs old. This home has lots of space and style to give you all the comfort and upgraded feel you want on vacation. Workspaces, formal dining area, tv's, and much more to give you everything you need while away from home. Plush comfortable beds, sound machines, and full gig wifi will help you sleep hard and work as needed! This home is centrally located to the fun trendy neighborhoods in Jax and even a quick drive to the beach!

Photos Details Inquire

$159/night

1430

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 6-9
Allows pets Internet
Must be min 25 yrs old. You will feel right at home and close to everything in this centrally located, very well decorated duplex home with super plush beds, sound machines, gig wifi and a huge back yard for your furry pets or your wild little ones! There are so many wonderful things about this home, you will need to stay here to believe it. And one of the best features of all.....Its all on one floor!

Photos Details Inquire

$119/night

1432

OwnerRez
1 Bedroom • 1 Bath • Sleeps 3-5
Allows pets Internet
Must be min 25 yrs old. You will feel right at home in this cozy spacious one bedroom home (duplex) with lots of space, a workspace, plush beds and a giant back yard for your furry friend or wild little one!

Photos Details Inquire

$149/night

1537

OwnerRez
3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 6-9
Allows pets Internet
Must be min 25 yrs old. You will feel right at home in this open stylish space that is central to all the trendy fun neighborhoods in Jacksonville. Fully fenced yard with peaceful landscaping will provide all the tranquility you are looking for and plenty of desks throughout the home to help you work when you need to!

Photos Details Inquire

$169/night

2680

OwnerRez
3 Bedrooms • 2 Baths • Sleeps 7-9
Allows pets Internet
Must be min 25 yrs old. You will fall in love with this cozy renovated stylish home that is spacious and feels good. Plush beds, nice linens, and sound machines will put you in a sound sleep and give you all the rest you need after exploring the fun neighborhood of riverside. This home is fully fenced and walking distance to many bars, restaurants, shops, etc.

Photos Details Inquire

$150/night

2694

OwnerRez
3 Bedrooms • 1 Bath • Sleeps 8-9
Allows pets Internet
Must be min 25 yrs of age to rent. This home has it all! Historic feel with all the modern comforts. Comfortable quality beds & linens, smart tv, cozy touches, multiple work spaces for all your remote needs, front porch rockers, off street parking for several cars, beautiful landscaping and centrally located to walk to coffee shops, bars, restaurants & more!

Photos Details Inquire