Holiday rentals near Theodore Roosevelt Area

We found 1,088 holiday rentals — enter your dates for availability

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July 2025

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Find the perfect holiday rental that's close to Theodore Roosevelt Area. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as a garden and pool. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Theodore Roosevelt Area

Showing deals for:3 Oct - 10 Oct

Chrome cast TV to stream your favorite shows from your device.

Exceptional

(16 reviews)

4 blocks from beach! spacious getaway w game room, outdoor kitchen. Kid-friendly

Jacksonville Beach, FL

12% off

AU$993 per night

includes taxes & fees

Exceptional

(60 reviews)

The Island Estate! Heated Salt Pool/Spa On The St John’s River! 9 Min To Beach!

Jacksonville, FL

8% off

AU$2,372 per night

includes taxes & fees

Spacious Living Room with Patio off the back and Electric Fireplace

Exceptional

(7 reviews)

Beautiful Townhome 2 Blocks from the beach with beach cruisers!

Jacksonville Beach, FL

8% off

AU$463 per night

includes taxes & fees

Exceptional

(5 reviews)

Charming 3/1 home in Jacksonville, 8 min to Stadium with Large Screen Porch

Jacksonville, FL

11% off

AU$276 per night

includes taxes & fees

Comfortable conversation set under covered pergola with sunshade and bug screen

Exceptional

(62 reviews)

Light Grey Getaway under 2 miles to mayo, 4 miles to the beach

Jacksonville Beach, FL

11% off

AU$443 per night

includes taxes & fees

Exceptional

(28 reviews)

Big Wheelchair Accessible Home Close to Beach/Mayo with Zen Den and Fenced Yard

Jacksonville Beach, FL

12% off

AU$519 per night

includes taxes & fees

Exceptional

(107 reviews)

Mayo Clinc 1mile from Intercoastal waterfront home w/pool and Breathtaking Views

Jacksonville Beach, FL

9% off

AU$572 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Theodore Roosevelt Area

Experience the warmth of Shady Oaks 3-bedroom ranch home near Mayo Clinic

Sleeps 6 · 3 bedrooms · 2 bathrooms

Top rated rentals - Theodore Roosevelt Area

Fantastic ocean views from the living room

Premier Host

Just perfection by the beach

We thoroughly enjoyed ourselves and the Happy pineapple was the perfection location and space. Everything is so well thought out for a perfect family visit. We had our 3 and 6 year old with us and all the beach toys left there for us was so useful and great we didn’t have to spend money on. The hosts were great and so responsive, we couldn’t of asked for better and location was perfect for restaurants too!! Salt lake, lynches and the Thai around corner we’re our favs. Thank you so much, we highly recommend to anyone. Marissa

Marissa P.

Stayed Oct 2019

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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value